Chemistry Part - 2

C h apter
ontents
CBSE–XII (PART-2)
Syllabus I - II
Sr.No. Topic Page No.
1. Haloalkene & Haloarene (Chapter-10) 001–026
2. Alcohol, Phenol & Ether (Chapter-11) 027–054
3. Aldehydes, Ketones and Carboxylic Acids (Chapter-12) 055-084
4. Amine (Chapter-13) 085-114
5. Biomolecules (Chapter-14) 115-136
6. Chemical Test 137-140
7. Name Reactions 141-148
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CBSE 1
HALOALKANES AND HALOARENES : (CHAPTER-10)

CHAPTER AT A GLANCE
Classification of Alkyl halide and Aryl halide :
Halogen Derivatives
Alkyl halides Alkenyl halides Alkynyl halides Aryl haides
Mono halides Di-halides Tri-halides Tetra halides
Primary halides Secondary halides Tertiary halides

General methods of Preparation of Alkyl halide ;
(1) By direct halogenation of alkanes :
U.V.light
R—H + Cl2 R—Cl + HCl
(excess)
(2) By the addition of H—X on alkenes :
R—CH = CHR + HX RCH2—CHXR
eg : CH2 = CH2 + HX CH3—CH2X
eg : CH3 – CH = CH2 + HX CH3 CH CH3
X
Isopropyl halide
(3) By Alcohols :
(a) By the action of hydrogen halides :
H X
R—CH2—OH RCH2—X
(b) By the action of phosphorous halides :
node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\10_Haloalkene & Haloarene
R—OH + PCl5 R—Cl + POCl3 + HCl

3R—OH + PCl3 3RCl + H3PO3
PBr3 and PI3 are less stable, thus for bromides ( P + Br2) and for iodides ( P + I2) mixture is used.
(c) By reaction with thionyl chloride (Darzen's procedure) :
Pyridine
R—OH + SOCl2 (1mole)
R—Cl + SO2 + HCl
One mole One mole
(4) By halide exchange :
dry acetone
R–Cl or R—Br + KI R–I + KCl or KBr (Finkelstein reaction)
2CH3Cl + Hg2F2 Water
2CH3–F + Hg2Cl2 (Swart reaction)
Note : Finkelstein reaction can only be used to prepare R–I and swart's reaction can only be used to
prepare R–F.

2 Chemistry
• Physical Properties
(a) The lower members CH3F, CH3Cl, CH3Br, C2H5Cl and C2H5F are gases at room temp.
(b) Higher B.P. than parent alkanes.
Decreasing order of B.P. is : R – I > R—Br > R—Cl > R—F
among isomeric R—X, decreasing order of B.P. is : Primary > Secondary > tertiary
(c) R—F and R—Cl lighter than water
R—Br and R—I heavier than water
Decreasing order of density is : R—I > R—Br > R—Cl > R—F
(d) R—X are polar co-valent compounds but insoluble in water because they cannot form
H–bonds. They dissolve in organic solvents.
(e) R—X (except R—F) burns with a green flame when interacted with Cu wire. (Beliestein test).
(f) Dipole moment order–
(i) CH3Cl > CH3F > CH3Br > CH3I (ii) Cl > Cl
Chemical Properties of Alkyl halide :

(I) Nucleophilic substitution reaction
+ –
Nu + C–X C – Nu + X (General NSR)
haloalkane
SN1 reaction :
SN2 reaction :
CH3Br + CH3OH + KBr
Methyl bromide Methyl alcohol
Bromo methane Methanol
(II) Elimination reactions
B: H
C=C +B–H+X–
C C
B = Base ; X = Leaving group

(III) Reaction with metals
Reaction with sodium (Wurtz reaction)

R – X + 2Na + X – R Dry ether
R – R + 2NaX

CBSE 3
Stereochemical Aspects of NSR :
(1) Ordinary light : These waves vibrates equally in all directions.
(2) Nicol prism: It is made by crystalline CaCO3 and paste with Canada balsom layer.
(3) Plane Polerised Light(PPL) : Such a beam of light which has vibrations only in one plane is
called PPL.
(4) Optically active compound : Certain compound rotate the plane polarized light when it is
passed through their solution by Nicol prism, such compounds are called optically active
compounds.
(5) Optical isomers and optical isomerism :
Optically active compounds rotate PPL clockwise and anticlockwise, on this basis such types of
compounds are two types:
(a) dextro rotatory or d or + compounds :
Compounds which rotates PPL towards clockwise called as dextro rotatory or 'd' or '+'
isomer.
(b) Laevo rotatory or or – compounds :
Compounds which rotates PPL towards anticlockwise called as laevo rotatory or 'l' or '-'
Such d and isomers of a compounds are called optical isomers and phenomenon is termed
as optical isomerism.
(6) Chiral or chirality :
The object which are non-superimposed on their mirror image, are called to be chiral and the
property is known as chirality.
(7) Achiral : The objects which are superimposed on their mirror images are called achiral.
(8) Enantiomers : Stereo isomers are mirror image of each other and cannot be superimposed on
each other, these isomers are enantiomers among them one is dextrorotatory and other of laevo
rotatory.
(9) Racemic mixture and racemisation :
A mixture containing two enantiomrers in equal proportions will have zero optical rotation as the
rotation due to one isomer with be cancelled by other iosomers. Such a mixture is known as
racemic mixture or racemic modification.
The process of conversion of enantiomers into a racemic mixture is known as racemisation.

# A racemic mixture is represented by prefixing d before the name.
SN1 reaction proceed with racemisation
*
CH3–CH–CH2–CH3 + KOH CH3–CH–CH2–CH 3 + KBr
Br OH
2-Bromobutane butan-2-ol
(Optically active) (Optically inactive)
SN2 reaction proceed with stereo chemical inversion.
CH3–CH–C6H13 + KOH CH3–CH–C6H13
Br OH
(–) 2-bromooctane (+) octan-2-ol

4 Chemistry
ESR of chlorobenznee
Name Reactions
1. Finkelstein Reaction 2. Swarts Reaction
3. Wurtz Reaction 4. Fittig Reaction
5. Wurtz-Fittig Reaction 6. Friedel-Crafts Reaction of chlorobenzene
7. Sandmeyer reaction 8. Gatterman reaction
Poly Halogen Compounds :
Carbon compounds containing more than one halogen atom are usually referred to as
polyhalogen compounds.
(1) Dicloromethane (CH2Cl2) :
(a) Dicloromethane is widely used as a solvent as a paint remover.
(b) It is also used as a metal cleaning and finishing solvent.
(c) In humans, direct skin contact with methylene chloride causes intense burning and mild
redness of skin.
(2) Trichloromethane(chloroform) (CHCl3) :
(a) Chloroform is used as general anesthetic in surgery.
(b) Chloroform is slowly oxidized by air in the presence of sunlight to an extremely poisonous
gas, carbonyl chloride, also known as phosgene.
It is therefore stored in closed dark colored bottles completely filled so that air is kept out.
light
2CHCl3 + O2 2COCl2 + 2HCl
Phosgene
(3) Triiodomethane (Iodoforms) :
Iodoforms used as antiseptic due to the liberation of free iodine and not due to iodoform itself.
(4) Tetrachloromethane(CCl4) / Carbontetrachloride / Pyrin :
Used as cleaning fluid, fire extinguisher.
(5) Freons : ChloroFlouroCarbon/CFCs : node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\10_Haloalkene & Haloarene
The chloro fluoro derivatives of methane and ethane are called freon.
DDT : Dichlorodiphenyltrichloroethane
Cl
Cl
Cl Cl
Cl
H
DDT
It is used as pesticides.

CBSE 5
EXERCISE-1 INTEXT QUESTIONS

1. Write the structure of the following compounds :
(i) 2-Chloro-3-methylpentane (ii) 1-Chloro-4-ethylcyclohexane
(iii) 4-tert. Butyl-3-iodoheptane (iv) 1, 4-Dibromobut-2- ene
(v) 1-Bromo-4-sec. butyl-2-methylbenzene
Cl
Cl CH3
1 2 3 4 5
Ans. (i) CH3–CH–CH–CH–CH3 (ii)
2-Chloro-3-methyl pentane
C2H5
1-Chloro-4-ethylcyclohexane
I
1 2 3 4 5 6 7 1 2 3 4
(iii) CH3–CH2–CH–CH–CH2–CH2–CH3 (iv) Br–CH2–CH=CH–CH2–Br
CH3 –C–CH3 1,4-Dibromobut-2-ene
CH3
4-tert-Butyl-3-iodoheptane
Br
1 2 CH3
6
(v) 5
4
3
CH3–CH–CH2–CH3
1-Bromo-4-sec-butyl-2-methylbenzene
2. Draw the structure of major monohalo products in each of the following reactions :
OH CH2CH3 Br2, heat or
(i) + SOCl2 (ii) O2N UV light
CH2OH heat
+ HCl CH3
(iii) HO (iv) + HI
heat
(v) CH3CH2Br + NaI (vi) + Br2
UV light
CH–CH3
Cl
Br
Ans. (i) (ii) O2N
4-(1-Bromoethyl)
Chlorocyclohexan
Nitrobenzenen
CH2Cl
CH3
(iii) HO (iv) I
4-Chloro methylphenol 1-Iodo-1methylcyclohexane
Br
(v) CH 3 CH 2 I (vi)
Iodoethane
3-Bromocyclohexane

6 Chemistry
3. Arrange each set of compounds in order of increasing boiling points.
(i) Bromomethane, Bromoform, Chloromethane, Dibromomethane.
(ii) 1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.
Br Br
Ans. (i) CH3–Cl < CH3–Br < CH2–Br < Br–CH–Br (increases M.W.)
Chloromethane Bromomethane Dibromomethane Bromoform
Cl
(ii) CH3–CH–CH3 < Cl–CH2–CH2–CH3 < Cl–CH2–CH2–CH2–CH3
Isopropyl chloride 1-Chloropropane 1-Chlorobutane
4. Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2
mechanism ? Explain your answer.
(i) CH3CH2CH2CH2Br or CH3CH2CHCH3
Br
CH3
(ii) CH CH CHCH or H C–C–Br
3 2 3 3
Br CH3
(iii) CH3CHCH2CH2Br or CH3CH2CHCH2Br
CH3 CH3
1
Ans. (i) S N 2
Hindrance on carbon
CH3CH2CH2CH2Br > CH3CH2CH–CH3
Br
1-Bromobutane (1°) 2-Bromobutane (2°)
(more hindrance)
CH3
(ii) CH3–CH2–CH–CH3 > CH3–C–Br
Br CH3
2-Bromobutane (2°) 2-Bromo-2-methylpropane (3°)
1° 1°
(iii) CH3–CH–CH2–CH2–Br > CH3–CH2–CH–CH2–Br
CH3 CH3
1-Bromo-3-methylbutane (1°) 1-Bromo-2-methylbutane (1°) node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\10_Haloalkene & Haloarene
(More hindrance)
5. In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction ?
Cl
Cl Cl
(i) and (ii) and Cl
Cl
Ans. (i) 2-Chloro-2-methylpropane (3°) 3° more stable

(I)
Cl
(ii)
2-Chloroheptane (2°) 2° more stable
(I)

CBSE 7
6. Identify A, B, C, D, E, R and R1 in the following :-
dry ether H 2O
Br + Mg A B
dry ether H 2O
Br + Mg A B
dry ether D2 O
R – Br + Mg C CH3CHCH3
D
CH3 CH3
Na ether Mg H2O
CH3––––––––––CH3 R1 – X D E
CH3 CH3
CH3
Ans. (A) MgBr (B) (C) CH3–CH–MgBr (D) H3C–C–MgBr
CH3 CH3
(E) CH3–CH–CH3
CH3
7. Write IUPAC names of the following :

H3C H
H CH3
(i) H
(ii) H
H Br
H Br
H3C
H3C
H3C CH3
H3C CH3
(iii) (iv)
H
H
H Br
H Br
H
H3C
H3C H
H CH3
(v) H (vi)
H
H Br
H Br
H
H
Ans. (i) 4-Bromopent-2-ene (ii) 3-Bromo-2-methylbut-1-ene

(iii) 4-Bromo-3-methylpent-2-ene (iv) 1-Bromo-2-methylbut-2-ene
(v) 1-Bromobut-2-ene (vi) 3-Bromo-2-methylpropene

8 Chemistry
8. Write the products of the following reactions :
(i) H + HBr (ii) CH3–CH2–CH = CH2 + HCl

H H
Peroxide
CH2– C = CH 2 + HBr
(iii) H
CH2– CH2– CH2– Br
Ans. (i) (ii) CH 3 CH 2 – CH CH3 (iii)

H |
Cl
H Br H H
9. Haloalkanes react with KCN to form alkyl cyanides as main product while AgCN forms
isocyanides as the chief product. Explain.
Ans. KCN is predominantly ionic and provides cyanide ions in solution. Although both carbon and
nitrogen atoms are in a position to donate electron pairs, the attack takes place mainly through
carbon atom and not through nitrogen atom since C—C bond is more stable than C—N bond.
However, AgCN is mainly covalent in nature and nitrogen is free to donate electron pair forming
isocyanide as the main product.
10. In the following pairs of hydrogen compounds, which would undergo SN2 reaction faster ?
CH2Cl and Cl ; and

I
Cl
Ans. CH2Cl It is primary halide and therefore undergoes SN2 reaction faster.
I As iodine is a better leaving group because of its large size, it will be

released at a faster rate in the presence of incoming nucleophile.
11. Predict the order of reactivity of the following compounds in SN1 and SN2 reactions : node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\10_Haloalkene & Haloarene
(i) The four isomeric bromobutanes

(ii) C6H5CH2Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br, C6H5C(CH3)(C6H5)Br
Ans. (i) CH3CH2CH2CH2Br < (CH3)2CHCH2Br < CH3CH2CH(Br)CH3 < (CH3)3CBr (SN1)
CH3CH2CH2CH2Br > (CH3)2CHCH2Br > CH3CH2CH(Br)CH3 > (CH3)3CBr (SN2)
(ii) C6H5C(CH3)(C6H5)Br > C6H5CH(C6H5) Br > C6H5CH(CH3)Br > C6H5CH2Br (SN1)
C6H5C(CH3)(C6H5) Br < C6H5 CH(C6H5) Br < C6H5CH(CH3)Br < C6H5CH2Br(SN2)

CBSE 9
EXERCISE-2 NCERT EXERCISE

1. Which compound in each of the following pairs will react faster in SN2 reaction with OH ?
(i) CH3Br or CH3I (ii) (CH3)3CCl or CH3Cl
Ans. (i) CH3 – I is more reactive because I is better leaving group than Br
CH3
(ii) H3C–C–Cl < CH3– Cl
CH3
In case of (CH3)3CCl, the attack of the nucleophile at the carbon atom is hindered of the presence
of bulky substituents on that carbon atom bearing the leaving group.
2. Predict all the alkenes that would be formed by dehydrohalogenation of the following halides
with sodium ethoxide in ethanol and identify the major alkene.
(i) 1-Bromo-1-methylcyclohexane
(ii) 2-Chloro-2-methylbutane
(iii) 2,2, 3-Trimethyl-3-bromopentane
Br CH3 CH3
Ans. (i) C2H 5ONa/C2H 5OH
+ HBr
(Only one alkene)
+
CH3 CH3 CH3
CH CH
C2H 5ONa/C2H 5OH
(ii) CH3–––CH2–––C–––CH3 –HBr
CH3–––CH=C –––CH3 + CH3–––CH2–––C=CH2
–HCl
Br
Cl 2-Methyl-2-butene (Major)
2-Methyl-2-butene major 2-Methyl-1-butene
2-Methyl-1-butene (Minor)
minor
+
CH3 Br CH3
C2H 5ONa/C2H 5OH
(iii) CH3–––C–––C–––CH2–––CH3 –HBr
CH3–––C–––C=CH–––CH3
CH3 CH3 CH3 CH3
3,4,4-Trimethypent -2-ene (I) (major)
+
CH3 CH2
CH3–––C–––C–––CH2–––CH3
CH3
2-Ethyl-3, 3-dimethybut-1-ene (II)
3. How will you bring about the following conversion ?

(i) Ethanol to but-1-yne (ii) Ethane to bromoethene
(iii) Propene to 1-nitropropane (iv) Toluene to benzyl alcohol
(v) Propene to propyne (vi) Ethanol to ethyl fluoride
(vii) Bromomethane to propanone (viii) But-1-ene to but-2-ene
(ix) 1-Chlorobutane to n-octane (x) Benzene to biphenyl
–+
Ans. (i) CH3–CH2–OH PCl5 CH3CH2–Cl CH C Na CH3CH2 C CH
But-1-yne
hv Alc.KOH H Br
(ii) CH 3 CH3 2Cl 2 CH 3 CHCl 2 CH CH 1mole
CH2 CH Br
(iii) CH 3 CH CH2 HBr Peroxide
CH3 CH 2 CH2 Br AgNO2
CH 3–CH
AgBr CH2–CH
3 2NO
CH d
2 2 CH 2NO 2
Pr opene 1 Bromopropane 1 Nitropropane

10 Chemistry
CH3 CH2Cl CH2OH
Cl2/UV light NaOH(aq)
NaOH(alc.)
(iv) or heat NaCl
Toluene Benzyl chloride Benzyl alcohol
Br2./CCl4 NaNH2
(v) CH3–CH=CH2 CH3–––CH–––CH2 LiqNH3
CH3–C CH
Propene Br Propyne
Br
1,2-Dibromopropane
PCl5 AgF
(vi) CH3–CH2–OH –POCl3, –HCl
CH3–CH2– Cl CH3–CH2–F
Ethanol Chloroethane
AgF
KCN (alc) CH3–MgBr H2O
(vii) CH3 – Br CH3 – CN CH3–C=NMgBr H3C–C = O
Bromomethane Acetonitrile
CH3
CH3
Hydrolysis H O +
Br
HBr KOH (alc)/
(viii) CH3CH2CH=CH2 (Markovnikov CH3CH2CHCH3 –HBr
CH3CH = CHCH3
But-1-ene addition) 2-Bromobutane 2–Butene
KOH (alc)/ –HBr

dry ether
(ix) 2CH3CH2CH2CH2–Cl + 2Na –2NaCl CH3CH2CH2CH2CH2CH2CH2CH3
1-Chlorobutane n-Octane
Cl
Br2/Fe
2
Br
Cl Na
(x) Anhydark
AlCl Dry ether
3
Benzene Chlorobenzene
Bromobenzene Diphenyl
4. Write the structure of the major organic product in each of the following reactions.
ace to ne ethanol
(i) CH 3 CH2 CH2 Cl Nal heat (ii) CH 3 3 CBr KOH heat
water aq.acetone
(iii) CH3 CH(Br)CH 2 CH 3 NaOH (iv) CH 3 CH2 Br KCN
(v) C6H5ONa + C2H5Cl (vi) CH3CH2CH2OH + SOCl2
Peroxide
(vii) CH3 CH2 CH CH2 HBr (viii) CH3CH = C(CH3)2 + HBr
Ans. (i) CH 3 CH 2 CH 2 I (ii) CH3–C = CH2

1 Iodopropane
CH3
(2-Methylpropene)
(iii) CH 3CH OH CH 2 CH3 (iv) CH3 CH 2 CN

Bu tan 2 ol Ethyl Cyanide
(v) C6 H 5 O C2 H 5 (vi) CH 3 CH 2CH 2 Cl

Phenetole 1 Chloropropane
Br
(vii) CH 3 CH 2CH 2 Br (viii) CH3–CH2–C–CH3
1 Bromobu tan e
CH3
2-Bromo-2-methylbutane

CBSE 11
EtOH H2 O
5. Write the mechanism of the following reaction : nBuBr KCN nBuCN
Ans. The given reaction is :
EtOH H2 O
nBuBr KCN nBuCN
The given reaction is an SN2 reaction.
C3H5 C3H 5 C3H5

–
C–Br NC C Br NC—C + Br
H H
H H H H
6. Arrange the compounds of each set in order of reactivity towards SN2 displacement :
(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
(ii) 1-Bromo-3-methylbutane,2-Bromo-2-methylbutane,3-Bromo-2-methylbutane
(iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane,1-Bromo-3-methylbutane.
Ans. (i) S N 1
2
Hindrance on carbon
Br Br
CH3CH2CH2CH2CH2 – Br > CH3CH2CH2CHCH3 > CH3CH2CCH3

CH 3
1-Bromopentane (1°) 2-Bromopentane (2°) 2-Bromo-2-methylbutane (3°)
CH3 Br Br
(ii) CH3CHCH2CH2Br > CH3CHCHCH3 > CH3CCH2CH3

CH 3 CH 3
1-Bromo-3-methylbutane 2-Bromo-3-methylbutane 2-Bromo-2-methylbutane
(1°) (2°) (3°)
CH3
CH3–CH2–CH2–CH2–Br CH3– CH–CH2–CH2–Br

(iii)
1-Bromobutane (1°) 1-Bromo-3-methylbutane (1°)
CH 3 CH3
CH3–CH2–CH–CH2–Br CH3–C–CH2–Br
CH 3
1-Bromo-2-methylbutane (1°) 1-Bromo-2, 2-dimethylpropane

(more branching at nearer distance)
Hence, the increasing order of reactivity of the given compounds towards SN2 is :
1-Bromo-2, 2-dimethylpropane < 1-Bromo-2-methylbutane < 1-Bromo-3-methylbutane < 1-
Bromobutane.
7. How the following conversions can be carried out ?
(i) Propene to propan-1-ol (ii) 1-Bromopropane to 2-bromopropane
(iii) Toluene to benzyl alcohol (iv) Benzene to 4-bromonitrobenzene
(v) Ethanol to propanenitrile (vi) Aniline to chloro benzene
(vii) 2- Chlorobutane to 3, 4-dimethylhexane (viii) 2-Methyl-1-propene to 2-chloro-2-methyl propane
(ix) Ethyl chloride to propanoic acid (x) But-1-ene to n-butyliodide
(xi) 2-Chloropropane to 1- propanol (xii) Chlorobenzene to p-nitrophenol
(xiii) 2-Bromopropane to 1-bromopropane (xiv) Chloroethane to butane
(xv) tert-Butyl bromide to isobutyl bromide

12 Chemistry
HBr/Peroxide Aq.KOH/ (i) BH3/THF
Ans. (i) CH3–CH=CH2 (Ani-Markovnikov
CH3–CH2–CH2–Br or CH3–CH=CH2 CH3–CH2–CH
CH CH–OH
CH –OH
1-Bromopropane
(Nucleophilic 2
(ii) H2O2/OH
3 2 2
Propene addition) Propan-1-ol

substitution)
(Nucleophilic
Aq KOH/
Br
KOH(alc)/ HBr
(ii) CH3–CH2–CH2–Br (Dehydrohalogenation)
CH3–CH=CH2 Markvnikov CH3–CH–CH3
1-Bromopropane Propene 2-bromopropane
addition
CH3 CH2Cl CH2–OH

Cl2
(iii) –HCl
KOH
Benzyl alcohol
Br Br
Br2/FeBr3 HNO3/H 2SO4
(iv) Dark (Nitration)
Benzene Bromobenzene NO2
4-Bromonitrobenzene
red P / Br2 KCN,Aq.ethanol
(v) CH3 Ethanol
CH 2 OH CH 3 CH
2
Bromoethane
Br CH 3 CH 2
Propanenitrile
CN
+ –
NH2 N2Cl Cl
NaNO2+2HCl,
273-278 K Cu 2Cl2
(vi) –NaCl, –2H 2O + N2
Aniline Benzenediazonium Chlorobenzene
chloride
Cl CH3 CH3
2Na/dry ether
(vii) 2CH3– CH– CH2–CH3 (Wurtz reaction) CH3–CH2–CH–CH–CH2–CH3 + 2NaCl
2-Chlorobutane 3, 4-Dimethylhexane
CH3 CH2
HCl
(viii) CH3–C=CH2 (Markovnikov
CH3–C–CH3
2-Methyl-1-propene addition) Cl
2-Chloro-2-methylpropane
KCN/aq. ethanol Hydrolysis
(ix) CH3–CH2–Cl (nucleophilic
CH3–CH2–CN + KCl
Nal/dry
CH3–CH2–COOH
substitution) Propanenitrile Propanoic acid
Ethylchloride acetone
NaI/dry
HBr/Peroxide acetone
(x) CH3–CH2–CH2–CH2—1
CH3– CH2–CH=CH2 (Anti-Markovnikov
CH3–CH2–CH2–CH2–Br
Bromobutane Finkeistein n- Butyl iodide
But-1-ene addition)
reaction
Cl
KOH(alc)/ (i) BH3/THF
(xi) CH3–CH–CH3 (Dethydrohalogenation)
CH3–CH=CH2
Propene (ii) H 2O2/OH
2-Chloropropane
HBr/Peroxide (Anti-Markovnikov
addition)
Aq. KOH/
CH3–CH2–CH2–OH (Nucleophilic
CH3–CH2–CH2–Br
1-Propanol substitution) 1-Bromopropane
Cl Cl Cl OH
HNO3/H 2SO 4 (i) NaOH, 433 K
(xii) (Nitration) (ii) dil HCl
Chlorobenzene NO2 2 NO2
p-Chloronitrobenzene
p-Chloronitrobenzene p--Nitrophenol
(Major product)

CBSE 13
Br
KOH(alc)/ HBr/peroxide
(xiii) CH3– CH–CH3 Dehydrohalogenation CH3–CH=CH2+HBr CH3–CH2–CH2–Br
Propene Anti-Markovikov 1- Bromopropane
2-Bromopropane addition
2Na / dryether
(xiv) CH3CH2 Cl Wurtz reaction
CH 3 CH 2 CH2 CH 3 2NaCl
Chloroethane Butane
Br
KOH(alc)/ HBr/Peroxide
(xv) CH3–C–CH3 Dehydrohalogenation
CH3–C=CH2 (Anit-Markovnikov
CH3–CH–CH2–Br
CH3 CH3 addition) CH3
Tert-Butylbromide 2-Methylpropene Isobutyl bromide
8. The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the
presence of alcoholic KOH, alkenes are major products. Explain.
Ans. OH– ion is highly solvated in an aqueous solution and as a result, the basic character of OH– ion
decreases. Therefore, it cannot abstract a hydrogen from the -carbon. So
R–Cl + Aq. KOH R–OH + KCl
On the other hand, an alcoholic solution of KOH contains alkoxide (RO–) ion, which is a strong
base. Thus, it can abstract hydrogen from the -carbon of the alkyl chloride and form an alkene
by eliminating a molecule of HCl.
R CH2 CH2 Cl KOH(alc) R CH CH 2 KCl H2O
Alkyl chloride Alkene
9. Primary alkyl halide C4H9Br(a) reacted with alcoholic KOH to given compound (b). Compound (b)
is reacted with HBr to give (c) which is an isomer of (a). When (a) is reacted with sodium metal
it gives compound (d), C8H18 which is different from the compound formed when n-butyl
bromide is reacted with sodium. Give the structural formula of (a) and write the equations for all
the reactions.
Ans. There are two primary alkyl halides having the formula, C4H9Br. They are n-butyl bromide and
isobutyl bromide.
CH3–CH2–CH2–CH2–Br CH3–CH–CH2–Br
n-Butyl bromide CH 3
Isobutyl bromide
2Na / dry ether
2CH 3CH 2CH 2CH 2Br (Wurtz reaction)
CH 3 CH2 CH2 CH2 CH2 CH2 CH2 CH 3 2NaBr
n Butyl bromide n-Octane
2Na/dry ether
CH3CHCH2Br (Wurtz reaction)
CH3CHCH2CH2CHCH3 +2NaBr
CH3 CH3 CH3
Isobutyl bromide (a) 2, 5-Dimethylhexane (d)
KOH (alc)/
CH3–CH–CH2–Br (Dehydrohalogenation)
CH3–C=CH2+HBr
CH3 CH3
Isobutyl bromide (a) 2-Methylpropene (b)
Br
HBr
CH3–C=CH2 (Markovnikov addition)
CH3–C–CH3
CH3 CH3
2-Methylpropene (b) 2-Bromo-2-methylpropane (c)
(an isomer of (a))

14 Chemistry
10. What happens when
(i) n-butyl chloride is treated with alcoholic KOH,
(ii) bromobenzene is treated with Mg in the presence of dry ether,
(iii) chlorobenzene is subjected to hydrolysis,
(iv) ethyl chloride is treated with aqueous KOH,
(v) methyl bromide is treated with sodium in the presence of dry ether,
(vi) methyl chloride is treated with KCN.
MgBr OH
(i) NaOH, 623 K, 300 atm
l Ans. (i) CH3 CH2 CH2 dry
CH+Mg ether
(ii)
KCl H2 O (iii)
But l ene
Chlorobenzene
Phenylmagenesium bromide Phenol
(iv) CH 3 CH 2 OH (v) CH 3 CH3 (vi) CH 3 CN

Ethanol Ethane Methyl cyanide
X
X
11. Out of and , which is an example of vinylic halide?
X
Ans.
12. The following compounds are given to you :

2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane
(a) Write the compound which is most reactive towards SN2 reaction.
(b) Write the compound which is optically active.
(c) Write the compound which is most reactive towards -elimination reaction.
Ans. (i) 1–Bromopentane (ii) 2–Bromopentane (iii) 2–Bromo–2–methylbutane
13. Write the major monohalo product(s) in each of the following reactions :-
CH2–CH=CH2
(i) +Br2 UV light

? (ii) +HBr
Peroxide
?
CH2OH
Heat
(iii) +HCl ?
OH
Br
CH2–CH2–CH2Br CH2Cl
Ans. (i) (ii) (iii)
HO

CBSE 15
14. Which of the following two reactions is SN2 and why ?
C2H5 C2H5
Y
(i) (ii) H H
X CH3 Y CH3
Retantion
Ans. (i) Inversion of configuration

15. Which would undergo SN2 reaction faster in the following pair :
C6H5 – CH2 – CH2 – Br and C 6H 5 – CH – CH 3
Br
Ans. C6H5–CH2CH2–Br
16. How do you convert the following :
(i) Prop-1-ene of Propan-2-ol (ii) Bromobenzene to 2-bromoacetophenone
(iii) 2-bromobutane to But-2-ene
H2O/H+
Ans. (i) CH3–CH=CH2 CH3–CH(OH)–CH3
Br Br O
C–CH3
(ii) CH3COCl/Anhy AlCl3
Br
KOH(Alc)
(iii) CH3–CH2–CH–CH 3 CH3–CH=CH–CH3 (or any other correct method)

(i) ethyl chloride is treated with NaI in the presence of acetone,
(ii) chlorobenzene is treated with Na metal in the presence of dry ether,
(iii) methyl chloride is treated with KNO2?
Write chemical equations in support of your answer.

Ans. (i) C2H5Cl + NaI Acetone
C2H 5I + NaCl
Dry ether
(ii) Cl + 2Na + Cl
+2NaCl
(iii) CH3Cl + KNO2 CH3–ONO + KCl

16 Chemistry
EXERCISE-3 RACE
Type 1 : Passage question 1 :-

The substitution reaction of alkyl halide mainly occurs by SN1 or SN2 mechanism. Whatever
mechanism alkyl halides follow for the substitution reaction to occur, the polarity of the carbon
halogen bond is responsible for these substitution reactions. The rate of SN1 reactions are governed by
the stability of carbocation whereas for SN2 reactions steric factor is the deciding factor. If the starting
material is a chiral compound, we may end up with an inverted product or racemic mixture depending
upon the type of mechanism followed by alkyl halide. Cleavage of ethers with HI is also governed by
steric factor and stability of carbocation, which indicates that in organic chemistry, these two major
factors help us in deciding the kind of product formed.
(a) When anisole is treatest with HI the product obtained is ?
(i) Phenol & methyl iodide (ii) Iodobenzene & methanol
(iii) Methyl iodide & methyl alcohol (iv) Phenol & methyl alcohol
(b) Name the instrument used for measuring the angle by which the plane polarised light is rotated.
(i) Nicol Prism (ii) Polarimeter
(iii) Polariser (iv) None of these
(c) Predict the major product formed when 2-Bromopentane reacts with alcoholic KOH.
(i) Pent-1-ene (ii) Pent-2-ene
(iii) Pentane (iv) But-1-ene
(d) The conversion of an alkyl halide into an alcohol by aqueous NaOH is classified as
(i) a dehydrohalogenation reaction (ii) a substitution reaction
(iii) an addition reaction (iv) a dehydration reaction
Type 2 : Assertion and Reason :-
Question 2 to 6 :- Note :- In the following questions a statement of assertion followed by a reason .
choose the correct answer out of the following choices –
(i) Both Assertion (A) and Reason (R) are correct statements, and Reason (R) is the correct
explanation of Assertion (A).
(ii) Both Assertion (A) and Reason (R) are correct statements, but Reason (R) is not the correct
(iii) Assertion (A) is correct, but Reason (R) is incorrect statement.
(iv) Assertion (A) is incorrect, but Reason (R) is correct statement.
2. Assertion : Aryl iodides can be prepared by reaction of arenes with iodine in the presence of an
oxidising agent.
Reason : Oxiding agent oxidises I2 into HI.

CBSE 17
3. Assertion : It is difficult to replace chlorine by –OH in chlorobenzene in comparison to that in
Chloroethane.
Reason : Chlorine-carbon (C—Cl) bond in chlorobenzene has a partial double bond character
due to resonance.
4. Assertion : Phosphorus chlorides (tri and penta) are preferred over thionyl chloride for the
preparation of alkyl chlorides from alcohols.
Reason : Thionyl chlorides give pure alkyl halides.
5. Assertion : KCN reacts with methyl chloride to give methyl isocyanide.
Reason : CN¯ is an ambident nucleophile.
6. Assertion : Presence of a nitro group at ortho or para position increases the reactivity of
haloarenes towards nucleophilic substitution.
Reason : Nitro group, being an electron withdrawing group decreases the electron density over
the benzene ring.
Type 3 : Multiple choice quation (one correct answer) (Queations 7 to 16):-
7. In the reaction R – OH + PBr3 RBr. The number of moles of alcohol that may be converted
in to akyl-bromide by one mole of PBr3 is
1
(i) 1-mole (ii) 2-moles (iii) 3-moles (iv) mole
3
8. A equimolar mixture of methyl iodide and ethyl iodide is heated with sodium and dry ether. The
number of possible alkane product is
(i) one (ii) two (iii) three (iv) four
9. The major product formed in the following reaction
CH 3
|
CH 3 C CH CH 3 HBr
| |
CH 3 OH
(i) (CH3)3CCHBrCH3 (ii) (CH3)3CCH = CH2

(iii) (CH3)2CBrCH(CH3)2 (iv) (CH3)2C = C(CH3)2
10. Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and paral halo
compounds. The reaction is
(i) Electrophilic elimination reaction (ii) Electrophilic substitution reaction
(iii) Free radical addition reaction (iv) Nucleophilic substitution reaction
11. Which reagent will you use for the following reaction ?
CH3CH2CH2CH3 CH3CH2CH2CH2Cl + CH3CH2CHClCH3
(i) Cl2 / UV light (ii) NaCl + H2SO4
(iii) Cl2 gas in dark (iv) Cl2 gas in the presence of iron in dark

18 Chemistry
12. The order of reactivity of following alcohols with halogen acids is ___________.
CH 3
|
(a) CH3CH2—CH2—OH (b) CH3 CH 2 CH OH (c) CH3 CH 2 C OH
| |
CH3 CH 3
(i) (a) > (b) > (c) (ii) (c) > (b) > (a) (iii) (b) > (a) > (c) (iv) (a) > (c) > (b)
13. Which of the following is halogen exchange reaction ?
(i) R X + NaI RI + NaX
C=C + HX C–C
(ii)
H X
ZnCl2
(iii) R – OH + HX R – X + H2O
CH3 CH3 CH3
(iv) Fe
+ X2 +
dark X
X
14. Arrange the following compounds in increasing order of their boiling points.
CH3
CH3 |
(a) CH – CH2Br (b) CH3CH2CH2CH2Br (c) H3 C C CH 3
CH3
|
Br
(i) (b) < (a) < (c) (ii) (a) < (b) < (c) (iii) (c) < (a) < (b) (iv) (c) < (b) < (a)
15. Chlorobenzene is formed by reaction of chlorine with benzene in the presence of AlCl3. Which of
the following species attacks the benzene ring in this reaction?
(i) Cl¯ (ii) Cl+ (iii) AlCl3 (iv) [AlCl4]¯
16. A primary alkyl halide would prefer to undergo _____________.
(i) SN1 reaction (ii) SN2 reaction (iii) –Elimination (iv) Racemisation
ANSWER KEY
Q. No. 1(a) (b) (c) (d) 2 3 4 5 6 7 8

Ans. (i) (ii) (ii) (ii) (iii) (i) (iv) (iv) (i) (iii) (iii)
Q. No. 9 10 11 12 13 14 15 16
Ans. (iii) (ii) (i) (ii) (i) (iii) (ii) (ii)

CBSE 19
EXERCISE-4 PREVIOUS YEARS QUESTION

1. In the following reaction : [CBSE Term-I, 2022]
CH3 CH3
R –X
Na/dry ether
CH3 CH3
CH3 CH3
R in the above reaction is
CH3 CH3 CH3 CH3 CH3

CH3
(a)CH3 CH2 (b) CH3 CH2 (c) CH3–C– (d) CH3 H
CH3 CH3 CH3 CH3 CH3 CH3
Ans. (c)
2. 2-Bromo-2-methylpropane is allowed to react with alcoholic KOH solution. The major product
formed is : [CBSE Term-I, 2021-22]
CH3 CH3
(a) CH3–C–OH (b) CH3–C–O–C2H5
CH3 CH3
CH3 CH3
– +
(c) CH3–C–O K (d) CH3 –C = CH2
CH3
Ans. (d)
CH3 CH
Alcoholic KOH
CH3 C CH2 H3C–C=CH2 + HBr
Br H
Alcoholic KOH is dehydrohalogenating agent.
3. Which of the following molecules is chiral in nature ? [CBSE Term-I, 2021-22]
Br Br
(a) CH3–C–CH3 (b) CH3–C–H

C2H5 C2H5
Br CH3
(c) CH3–C–H (d) CH3–C–CH2–Br
CH3 C2H5
Ans. (b)
Br
H3C C* H
C2H5
The carbon which have four different atom/group of atoms, known as chiral carbon.

20 Chemistry
4. An SN1 reaction of an enantiomerically pure chiral alkyl halide gives a product :
[CBSE Term-I, 2021-22]
(a) with retention of configuration (b) with inversion of configuration
(c) with recemisation (d) with partial racemisation
Ans. (c) Racemisation
In case of optically active alkyl halides, SN1 reactions are accompained by racemisation.
5. Which of the following is most reactive towards nucleophilic substitution reaction ?
[CBSE Term-I, 2021-22]
Cl Cl Cl Cl
CH3 CH3
(a) (b) (c) (d)
NO2 CH3 CH3

Ans. (a) Due to –NO2 is electron withdrawing group. increases the Reactivity of Haloarenes.
6. Which of the following belongs to the class of allylic halides ? [CBSE Term-I, 2021-22]
X
X
(a) (b) (c) (d)
X
Ans. (d)
3
sp
3
sp
CH2–X 3
Allylic halide sp
These are the compounds in which halogen atom is borded to an sp3 hybridised carbon atom next
to C = C i.e. to an allylic carbon.
7. Out of the following, the one which is most reactive towards nucleophilic substitution reaction is
[CBSE Compartment, 2021]
(A) CH2 = CH – Cl (B) C6H5 – Cl
(C) CH3CH = CH – Cl (D) CH3 – CH2 – CH2 – Cl
Ans. (D)
8. Give reasons : [CBSE Compartment, 2021]
(a) Grignard reagent should be prepared under anhydrous conditions,
(b) Alkyl halides are immiscible with water although they are polar, and node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\10_Haloalkene & Haloarene
(c) Chloroform is stored in dark coloured bottles filled up to the brim. [1 × 3 = 3]

Ans. (a) Grignard reagents in the presence of moisture, they react with H2O to give alkanes.
R Mg X H 2O R H Mg(OH)X
Grigrard Alkane
reagent
(b) The molecules of water are held together by hydrogen bonds, As the new force of attraction
between water and alkyl halide molecules are weaker than the forces of attraction already
existing between alkyl halide- alkyl halide molecules and water-water molecules, they cannot
form H-bond with water.
(c) Chloroform is slowly oxidised by air in the presence of light to an extremely poisonous gas
phosgene (carbonyl chloride). It is therefore stored in closed dark coloured bottles completely
filled so that air is kept out.
2CHCl3 + O2 Light 2COCl2 + 2HCl
Phosgene

CBSE 21
9. Read the given passage and answer the questions number 1 to 5 that follow : 1× 5 = 5
The substitution reaction of alkyl halide mainly occurs by SN1 or SN2 mechanism. Whatever
mechanism alkyl halides follow for the substitution reaction to occur, the polarity of the carbon
halogen bond is responsible for these substitution reactions. The rate of SN1 reactions are
governed by the stability of carbocation whereas for SN2 reactions steric factor is the deciding
factor. If the starting material is a chiral compound, we may end up with an inverted product or
racemic mixture depending upon the type of mechanism followed by alkyl halide. Cleavage
of ethers with HI is also governed by steric factor and stability of carbocation, which
indicates that in organic chemistry, these two major factors help us in deciding the kind of
product formed. (CBSE 2020)
(i) Predict the stereochemistry of the product formed if an optically active alkyl halide undergoes
substitution reaction by SN1 mechanism. [1]
(ii) Name the instrument used for measuring the angle by which the plane polarised light is
rotated. [1]
(iii) Predict the major product when 2-Bromopentane reacts with alcoholic KOH. [1]
(iv) Give one use of CHI3. [1]
(v) Write the structures of the products formed when anisole is treated with HI. [1]
Ans. (i) Racemic Mixture
(ii)Polarimeter
(iii) Pent-2-ene/CH3CH=CHCH2CH2
(iv) Antiseptic
(v) CH3I + C6H5OH
10. Out of Chlorobenzene and Cyclohexyl chloride, which one is more reactive towards nucleophilic
substitution reaction and why ? [1]
(CBSE 2019)
Ans. Cyclohexyl chloride; Because of partial double bond character of C–Cl bond in Chlorobenzene/
3 2
Resonance effect / sp hybridised carbon in cyclohexyl chloride whereas sp carbon in
chlorobenzene.
11. Among all the isomers of molecular formula C4H9Br, identify :

(a) The one isomer which is optically active. (CBSE 2019)
(b) The one isomer which is highly reactive towards .
(c) The two isomers which give same product on dehydrohalogenation with alcoholic KOH. [3]
Ans. (a) CH3CH2CH(Br)CH3
(b) CH3CH2CH2CH2Br
(c) (CH3)3Br and (CH3)2CHCH2Br
12. Out of Chlorobenzene and p-nitrochlorobenzene, which one is more reactive towards nucleophilic
substitution reaction and why ? [1]
(CBSE 2019)
Ans. p-nitrochlorobenzene undergoes nucleophilic substitution reaction faster than chlorobenzene due
to resonance effect.

22 Chemistry
13. Out of chlorobenzene and benzyl chloride, which one gets easily hydrolysed by aqueous NaOH
and why ? (CBSE 2018)
Cl CH2Cl
Ans.
The benzyl chloride is more hydrolysed in aquation NaOH as in chloro benzene the lone pair of
chlorine are in conjugation with -Bond of benzene due to which partial double bond character
develop & it reduce its reactivity.
14. (a) Identify the chiral molecule in the following pair : (CBSE 2018)
OH & OH
(i) (ii)
(b) Write the structure of the product when chlorobenzene is treated with methyl chloride in
the presence of sodium metal and dry ether.
(c) Write the structure of the alkene formed by dehydrohalogenation of 1-bromo-1-
methylcyclohexane with alcoholic KOH.
Ans. (a) The chiral molecule. (b)

OH
Br CH3 CH3 CH2
(c) Alc. KOH/

+
(major) (minor)

CBSE 23
EXERCISE-5 MOCK TEST

1. Write the IUPAC name of following compound. [1]
H CH3
H
H
H Br
X
X
2. Out of and , which is an example of vinylic halide ? [1]
3. Which would undergo SN2 reaction faster in the following pair : [1]
C6H5 – CH2 – CH2 – Br and C6H 5 – CH – CH 3
Br
4. Which one of the following compound is more easily hydrolysed by KOH & Why. [2]
CH3CHClCH2CH3 or CH3CH2Cl
5. Write the structure of the product when chlorobenzene is treated with methyl chloride in the
presence of sodium metal and dry ether. [2]
6. Complete reaction : [2]
CH3
(i) + HI ?
(ii) CH3CH2CH=CH2 + HBr ?

7. Write a chemical test to distinguish between [2]
(a) Chlorobenzene & benzyl chloride
(b) Chloroform & CCl4
8. Suggest a possible mechanism for the reaction n BuBr + KCN n-BuCN [3]
9. Give reasons for the following [3]

(i) Ethyl iodide undergoes SN2 reaction faster than ethyl bromide
(ii) (±) 2-Butanol is optically inactive.
(iii) C–X bond length in halobenzene is smaller than C–X bond length in CH3–X.

24 Chemistry
10. How do you convert the following : [3]
(i) Prop-1-ene of Propan-2-ol
(ii) Bromobenzene to 2-bromoacetophenone
(iii) 2-bromobutane to But-2-ene
11. Write the major monohalo product(s) in each of the following reactions : [5]
UV light
(i) +Br2 ?
CH2–CH=CH2
Peroxide
(ii) +HBr ?
CH2OH
Heat
+HCl ?
(iii)
OH
PCl5
(iv) CH2OH

(v) CH2–CH = CH 2 + HBr

CBSE 25
MOCK TEST SOLUTIONS
1. 3-bromo-2-methyl prop-1-ene
X
2.
3. C6H5 – CH2CH2 – Br
4. CH3CHClCH2CH3 is more reactive than CH3CH2CH2CH2Cl as the former one gives more stable
carbocation intermediate.
H3C H H3C H – HC
H
C OH
+ 3
CCl C— OH
H3CCH2 H3CCH2 H3CH2C
Cl CH3
5. Na
+ CH3–Cl
dry ether
Toluene
CH3
6. (i) I
(ii) CH3–CH2–CH–CH3
Br
7. (a) Benzyl chloride when treated with AgNO3 solution will give a white ppt. while chlorobenzene will not.
(b) CHCl3 when treated with 1º amine & KOH gives offensive smelling isocyanides while CCl4
does not show this test.
C3H5 C3H5
C3H5 –
8. C–Br NC C Br NC—C + Br
H H
H H H H

26 Chemistry
9. (i) Iodide is better leaving group because of its larger size than bromide therefore ethyl idoide
under goes SN2 reaction faster than ethyl bromide.
(ii) +2 butanol is a racemic mixture it is a mixture which contains two enatiomers in equal
proportion and thus have zero optical rotation so it is optically inactive.
(iii) Due to delocalisation of lone pairs of electron of X atom over the benzene ring. C-X bond in
halogenzen acquire some double bond character while in CH3-X, C-X bond is a single bond.
H2 O/H
10. (i) CH 3 CH CH 2 CH 3 CH(OH) CH 3
Br Br O
CH3COCl/Anhy AlCl3 C–CH3
(ii)
Br
|
KOH(Alc)
(iii) CH 3 CH 2 CH CH 3 CH 3 CH CH CH 3 (or any other correct method)
Br CH2Cl
CH2–CH2–CH2Br
11. (i) (ii) (iii)
HO
(iv) CH2Cl (v) CH2–CH – CH3 node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\10_Haloalkene & Haloarene
Br

CBSE 27
ALCOHOL, PHENOL & ETHER : (CHAPTER-11)

CHAPTER AT A GLANCE
PART-I : ALCOHOL
Topic : Naming and Classification of alcohols
I. Based on no. of –OH groups
(i) Monohydric alcohol (ii) Dihydric alcohol (iii) Tri Hydric alcohol
CH 2 OH
CH 2 OH |
| CH OH
C2H5OH CH 2 OH |
CH 2 OH
Ethyl alcohol Ethylene glycol Glycerol
II. Compound containing Csp 3 OH :
In this class of alcohol the –OH group is attached to an sp3 hybridised carbon atom of alkyl group.
They are further classified as follows
Classification of Monohydric alcohols on the basis of position of –OH group :
(A) Primary, Secondary, Tertiary alcohols :
(i) Primary alcohol (ii) Secondary alcohol (iii) Tertiary alcohol
R
1º 3°
R – CH2 – OH R 2º R – 3C – OH
3
CH – OH sp
sp
R sp3 R
Functional : – CH 2 – OH
group Functional : CH – OH Functional : – C – OH
group group
CH3
H 3C
e.g. CH3–OH e.g. CH–OH H3C–C–OH
Methyl alcohol
H 3C CH3
Isopropyl alcohol ter.butyl alcohol
CH3–CH–CH2–CH3
CH –CH –OH
3 2 OH
Ethyl alcohol sec. butyl alcohol
node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
3
sp
(B) Allylic alcohols : CH2 = CH – CH2 –
allyl group
3
sp
(i) Primary allylic alcohol CH2 = CH – CH2 – OH
H
(ii) Secondary allylic alcohol CH2 = CH – C – OH
–C–
–C–
(iii) tertiary allylic alcohol CH2 = CH – C – OH
–C–

28 Chemistry
(C) Benzylic alcohol :
3 sp3
sp
CH2 –
C 6H 5 – CH2 – Benzyl group
sp3 –C– –C–
CH2 – OH
H – C – OH –C – C – OH
Benzyl alcohol
(primery) Secondary Tertiary
Topic : Reaction Mechanism
1. Write mechanism of following reaction
+
H
C=C + H2O C–C
dil. H 2SO4
H OH
2. Write the mechanism of preparation of Ethene from Ethanol ?
H2SO4
CH3 CH2 OH 443K
CH 2 CH 2
3. Write the mechanism of preparation of Ethanol to Ethoxyethane.
2C2H5OH C2H5OC2H5
Topic : General method of preparations of alcohols
1. From alkene
(i) By acid catalysed hydration of alkene
(ii) By hydroboration oxidation of alkene
2. From carbonyl compound : By reduction of aldehyde and ketone
3. By reduction of carboxylic acid and acid derivatives
4. Formation of Alcohol from Haloalkenes
5. Formation of alcohol by Aliphatic amine
6. From Grignard reagent
Carbonyl compound i.e. aldehyde and ketone shows nucleophilic addition reaction.
Topic : Chemical Reaction of alcohol (R – OH) node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
Chemical Reaction of Alcohol (R – OH)
I. Reactions involving II. Reactions involving III. Reaction involving

cleavage of R–O–H bond cleavage of carbon-oxygen (C-O) complete molecule
R – OH of alcohol (R–OH)
bond in alcohols
(I) Reactions involving cleavage of
–O–H bond cleavaging order in these type of reactions :
Primary alcohol > Secondary alcohol > Tertiary alcohol
1. Reaction with metal
2. Esterification

CBSE 29
(II) Reaction involving cleavage of carbon-oxygen (C – OH) bond in alcohol (R – OH)
1. Reaction with halogen acids

2. Reaction with PCl3/PCl5/SOCl2
3. Dehydration of alcohols (Elimination reaction)
4. Oxidation
5. Catalytic Dehydrogenation
Topic : Some Commercially Important Alcohols
Methanol and ethanol are among the two commercially important alcohols.
1. Methanol : Methanol, CH3OH, also known as ‘wood spirit’, was produced by destructive
distillation of wood.
Preparation : Methanol is produced by catalytic hydrogenation of carbon monoxide at high
pressure and temperature and in the presence of ZnO – Cr2O3 catalyst.
ZnO –Cr2 O3
CO 2H 2 200–300atm
CH3OH
573–673K
Properties : Methanol is a colourless liquid and boils at 337 K. It is highly poisonous in nature.
Ingestion of even small quantities of methanol can cause blindness and large quantities causes
even death.
Uses : Methanol is used as a solvent in paints, varnishes and chiefly for making formaldehyde.
2. Ethanol :
Preparation : Ethanol, (C2H5OH), is obtained commercially by fermentation, the oldest method
is from sugars. The sugar in molasses, sugarcane or fruits such as grapes is converted to
glucose and fructose, (both of which have the formula C6H12O6), in the presence of an enzyme,
invertase. Glucose and fructose undergo fermentation in the presence of another enzyme,
zymase, which is found in yeast.
C12H22O11 + H2O Invertase
C 6 H12 O 6 C6 H12 O 6
Glu cos e Fructose
C6H12O6 Zymase
2C2H5OH+ 2CO2
Properties : Ethanol is a colourless liquid with boiling point 351 K.
Uses :
It is used as a solvent in paint industry and in the preparation of a number of carbon compounds.

30 Chemistry
PART-II : ETHER
Topic : Naming
(i) Simple ether or symmetrical ether :
The ethers in which similar alkyl groups are attached to the divalent oxygen (i.e. functional group
of –O– ether) known as simple ether.
Structure Common name IUPAC
R–O–R Dialkyl ether Alkoxy alkane
1. CH3–O–CH3 Dimethyl ether Methoxy methane
2. CH3–CH2–O–CH2–CH3 Diethyl ether Ethoxy ethane
(ii) Mixed ether or unsymmetrical ether :
The ethers in which different alkyl groups are attached to the divalent oxygen (–O–) is known as
mixed or unsymmetrical ether.
Structure Common name IUPAC
R–O–R' Alkyl Alkyl' ether Alkoxy alkane
1. CH3–O–CH2–CH3 Ethyl methyl ether Methoxy ethane
CH3
2. H3C–C–O–CH3 ter Butyl methyl ether 2-Methoxy-2-methyl propane
CH3
Aromatic ether :
OR
(Ar–O–R)
Alkyl aryl ether
General Method of Preparation of Ether

1. By dehydration of alcohols
2. Williamson synthesis reaction / Williamson ether synthesis reaction
(A) Formation of simple ether (symmetrical ether)
– ..
R – X + R – ONa R–O
.. – R + NaX
Alkyl halide Sodium Symm.
alkoxide Ether
(B)Formation of unsymmetrical ether
R – X + R' – ONa
..
R–O .. – R + NaX
Chemical reactions of ethers :
1. Reaction with halogen acids : Cleavage of C–O bond in ethers.
Topic : Anisole
Preparation of anisole
–+
OH ONa OCH3
+NaOH CH3Cl
Phenol Sodium Anisole

phenoxide
Electrophilic substitution reactions
(i) Halogenation
(ii) Friedel-Crafts reaction : (A) Alkylation (B) Acetylation
(iii) Nitration

CBSE 31
PART-III PHENOL
TOPIC : NAMING
Phenol : The simplest hydroxy derivative of benzene is known as phenol in which – OH group
attached with sp2 hybridised carbon of benzene.
Functional group of phenol : C 2– OH
sp
Nomenclature of Phenol & examples of phenolic compounds :

CH3
CH3 CH3
OH
OH
OH OH
Common Name Phenol o-Cresol m-Cresol p-Cresol
IUPAC Name Phenol 2-Methylphenol 3-Methylphenol 4-Methylphenol
OH
OH OH
OH
OH OH
Common name Catechol Resorcinol Hydroquinone or quinol
Benzene-1,2-diol Benzene-1,3- diol Benzene-1,4- diol
Topic : General Method of Preparation of Phenol

1. From haloarenes 2. From benzenesulphonic acid
3. From diazonium salts 4. From cumene
Topic : Electrophilic Substitution reaction of Phenol
1. Nitration of Phenol
(a) With dilute HNO3 (b) With conc. HNO3
2. Halogenation
(a) With liquid bromine (b) With bromine water

3. Kolbe’s reaction 4. Reimer-Tiemann reaction
5. Reaction of phenol with zinc dust 6. Oxidation
Topic : Name Reactions
1. Friedel-Crafts alkylation Reaction of Anisole
2. Friedel-Crafts acylation reaction
3. Reimer-Tiemann Reaction
4. Kolbe’s Reaction
5. Williamson's ether synthesis reaction

32 Chemistry
1. Name the following compounds according to IUPAC system.

CH2OH CH2OH
OH
(i) CH3–CH2–CH–CH–CH–CH3 (ii) CH3–CH–CH2–CH–CH–CH3 (iii)

CH2Cl CH3 CH3 OH Br
H2C=CH–CH–CH2–CH2–CH3
(iv) (v) CH3 – C = C – CH2OH
OH CH3 Br
Ans. (i) 3-Chloromethyl - 2- isopropylpentan-l-ol
(ii) 2, 5 - Dimethylhexane - 1, 3 – diol (iii) 3-Bromocyclohexanol
(iv) Hex-1-en-3-ol (v) 2-Bromo-3-methylbut-2-en-1-ol
2. Write structures of the products of the following reactions :
O O
NaBH4
(i) CH3 CH CH2 H2 O / H
(ii) CH2 – C–O–CH3
H
NaBH4
(iii) CH –CH –CH–CHO
3 2
CH3
O OH
CH2–C–OCH3
Ans. (i) CH3–CH–CH3 (ii)
O H O
OH
Propan-2-ol
Methyl (2-hydroxycyclohexyl)
ethanoate
(iii) CH3–CH2–CH–CH2OH
CH3
2-Methylbutan-l-ol
3. Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the
corresponding phenoxide ions.
– –
O O O O O
Ans. –
–
–
(Resonance structure of the phenoxide ion)
O O O O O O
N+ N+ N+ N+ N+ N+
— — — —
O O O O O O O O—
—
O O
—
O O
(Resonance structures of p-nitrophenoxide ion)
– –
O O O
—
O O O
O O O O
+
N +
+
N N N N
O— O
—
O— – + O— —
O
–
(Resonance structures of o-nitrophenoxide ion)
It can be observed that the presence of nitro groups increases the stability of phenoxide ion.

CBSE 33
4. Predict the products of the following reactions :
OC2H5
(i) CH3–CH2–CH2–O–CH3 + HBr (ii) + HBr
OC 2H5 Conc.H SO
(iii) 2
Conc.HNO3
4
(iv) (CH 3 )3 C OC2 H5 HI
OC H OH
+ C2H5Br (SN2)
Ans. (i) CH3–CH2–CH2–OH –CH3–Br (SN2) (ii)
Propanol Bromomethane Ethoxybenzene Phenol Bromoethane
OC H Conc.H2SO4 OC 2H5 OC2H5

(iii)
Conc.HNO 3 + (CH3 )3 C(Nitration)
OC2 H 5 (iv) (CH 3 )3 C I C 2 H5 OH (S N 1)
tert Butyl ethyl ether tert Butyliodide Ethanol
NO2 NO2
Ethoxybenzene 1-Ethoxy-4-nitrobenzene 2-Ethoxynitrobenzene
(Major) (Minor)
5. Give IUPAC names of the following compounds :

(i) CH —CH—CH—CH—CH OH
3 2 (ii) CH3 —CH—O—CH2CH3
—
—
Cl CH3 CH3 CH3
OH NO2
H3C CH3 OC2H5
(iii) (iv)
Ans. (i) 4-Chloro-2,3-dimethylpentan-1-ol (ii) 2-Ethoxypropane
(iii) 2,6-Dimethylphenol (iv) 1-Ethoxy-2-nitrocyclohexane

6. Arrange the following sets of compounds in order of their increasing boiling points:
(a) Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol.
(b) Pentan-1-ol, n-butane, pentanal, ethoxyethane.
Ans. (a) Methanol, ethanol, propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol.
(b) n-Butane, ethoxyethane, pentanal and pentan-1-ol.
7. Arrange the following compounds in increasing order of their acid strength: Propan-1-ol, 2, 4,
6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-methylphenol.
Ans. Propan-1-ol, 4-methylphenol, phenol, 3-nitrophenol, 3, 5-dinitrophenol, 2, 4, 6-trinitrophenol.

8. Write the structures of the major products expected from the following reactions:
(a) Mononitration of 3-methylphenol
(b) Dinitration of 3-methylphenol
(c) Mononitration of phenyl methanoate.
Ans. The combined influence of –OH and –CH3 groups determine the position of the incoming group.
OH OH OH OCOCH3
O2N O2N
(a) and (b) (c)

CH3 CH3 CH3
NO2 NO2 NO2

34 Chemistry
9. The following is not an appropriate reaction for the preparation of t-butyl ethyl ether.
CH3 CH3
C2 H5 ONa + CH3 —C—Cl CH 3 —C—OC 2H 5
CH3 CH 3
(i) What would be the major product of this reaction ?
(ii) Write a suitable reaction for the preparation of t-butylethyl ether.
Ans. (i) The major product of the given reaction is 2-methylprop-1-ene.
It is because sodium ethoxide is a strong nucleophile as well as a strong base. Thus elimination
reaction predominates over substitution.

CH 3 CH3
+
(ii)
: :
CH3—C—CONa+CH3 CH2Cl CH 3 —C—OC2H5

CH3 CH 3
CH3 CH 3
10. (i) CH3 — CH2—CH—CH2—O—CH2 —CH3
CH3
— —
(ii) CH3—CH2 —CH2—O—C—CH2 —CH3

CH3
(iii) CH2—O—
Ans. (i) CH3 —CH2—CH—CH2OH + CH3 CH2I

CH3
CH3
— —
(ii) CH3CH2CH2OH + CH3CH2—C—I

CH3
(iii) CH2I + —OH

CBSE 35

1. Show how will you synthesize :
(i) l-phenylethanol from a suitable alkene.
(ii) cyclohexylmethanol using an alkyl halide by an SN2 reaction
(iii) pentan-1-ol using a suitable alkyl halide ?
CH2Cl CH2OH
CH=CH2 + CH–CH3
H
Ans. (i) +H2O OH (ii) + aq. NaOH + NaCl
Phenylethene 1-phenylethanol Chloromethylcyclohexane Cyclohexylmethanol
(iii) CH3CH2CH2CH2CH2Cl + aq. NaOH CH3CH2CH2CH2CH2OH + NaCl

1-Chloropentane Pantan-1-ol
2. Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that of
ethanol.
Ans. The acidic nature of phenol can be represented by the following two reactions.
(i) Phenol reacts with sodium to give sodium phenoxide, liberating H2.
OH ONa
+ Na + 1 H2
2
Phenol Sodium phenoxide
(ii) Phenol reacts with sodium hydroxide to give sodium phenoxide and water as by-products.
OH ONa
+ NaOH + H2O
Sodium phenoxide
The acidity of phenol is more than that of ethanol. This is because after losing a proton, the
phenoxide ion undergoes resonance and gets stabilized whereas ethoxide ion does not.
O O O O O
3. How are the following conversions carried out ?

(i) Propene Propan-2-ol
(ii) Benzyl chloride Benzyl alcohol
(iii) Ethyl magnesium chloride Propan-1-ol.
(iv) Methyl magnesium bromide 2-Methylpropan-2-ol.
Ans. (i) CH –CH=CH +H O H CH –CH–CH

3 2 2 3 3
OH
Propene Propan–2–ol
CH2Cl CH2ONa CH2OH
H+
(ii) + NaOH
NaCl
Benzyl chloride Benzyl alcohol
C
Et2H5
– + H
+
(iii) H–C–H + CEt2HMg Cl

5MgCl
H–C–H Et–CH
CH3CH2–OH + Mg(OH)Cl
2CH2–OH +Mg(OH)Cl
O OMgCl
CH3 OH
H3C – + H2O
(iv) C=O+CH3–MgBr CH3–C–OMgBr CH3–C–CH3 + Mg(OH)Br
H3C
CH3
Adduct CH3
2-Methylpropan-2-ol

36 Chemistry
4. Name the reagents used in the following reactions :
(i) Oxidation of a primary alcohol to carboxylic acid.
(ii) Oxidation of a primary alcohol to aldehyde.
(iii) Bromination of phenol to 2,4,6-tribromophenol.
(iv) Benzyl alcohol to benzoic acid.
(v) Dehydration of propan-2-ol to propene.
(vi) Butan-2-one to butan-2-ol.
Sol. (i) Acidified potassium permanganate (ii) Pyridinium chlorochromate (PCC)
(iii) Bromine water (iv) Acidified potassium permanganate
(v) 85% phosphoric acid (vi) NaBH4 or LiAlH4
5. Illustrate with examples the limitations of Williamson synthesis for the preparation of certain
types of ethers.
Ans. The reaction of Williamson synthesis involves SN2 attack of an alkoxide ion on a primary alkyl
halide.
CH3 CH3
+
CH3–C–O Na + CH3 – Cl CH3–O–C–CH3 + NaCl
CH3 CH3
But if secondary or tertiary alkyl halides are taken in place of primary alkyl halides, then
elimination would compete over substitution. As a result, alkenes would be produced. This is
because alkoxides are nucleophiles as well as strong bases. Hence, they react with alkyl halides,
which results in an elimination reaction.
CH3
CH3–C–Cl +NaO–CH3 CH3–C=CH2 + CH3OH + NaCl
CH3 CH3
Tertiary alkyl halide Alkene
6. How is l-propoxypropane synthesised from propan-1-ol ? Write mechanism of this reaction.

+
H
2CH3CH2CH2–OH CH3CH2CH2–O–CH2CH2CH3
Ans. Propane-1-ol 1-Propoxypropane
The mechanism of this reaction involves the following three steps :

Step 1 : Protonation
+ H
H +
CH3CH2CH2–O–H CH3CH2CH2–O –H
Propane-1-ol
Step 2 : Nucleophilic attack

+ H +
CH3CH2CH2–O + CH3–CH2–CH2–O CH3CH2CH2–O–CH2–CH2–CH3
H
H H
+
H2 O
Step 3 : Deprotonation
+ +
CH3CH2CH2–O–CH3CH2CH2 CH3CH2CH2 – O – CH2CH2CH3 + H
H 1-Propoxypropane

CBSE 37
7. Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable
method. Give reason.
Ans. The formation of ethers by dehydration of alcohol is a bimolecular reaction (SN2) involving the
attack of an alcohol molecule on a protonated alcohol molecule. In this method, the alkyl group
should be unhindered. In case of secondary or tertiary alcohols, the alkyl group is hindered. As a
result, elimination dominates substitution. Hence, in place of ethers, alkenes are formed.
8. Write the equation of the reaction of hydrogen iodide with :
(i) 1-propoxypropane (ii) Methoxybenezene and (iii) Benzyl ethyl ether
373 K
Ans. (i) C H CH –O–CH C H + HI
2 5 2 CH CH CH –OH+CH CH CH – I
2 2 5 3 2 2 3 2 2
l-Propoxypropane Propan-1-ol 1-Iodopropane

OCH3 OH CH2–O–C2H5 CH2l
(ii) + HI + CH3–I (SN2) (iii) + HI + C2H5–OH (SN1)
Methoxy benzene Phenol Benzyl ethyl ether Benzyl iodide Ethanol
9. Write the mechanism of the reaction of HI with methoxymethane.

Ans. The mechanism of the reaction of HI with methoxymethane involves the following steps :
H
Step1 : Protonation of methoxymethane : CH3–O–CH3 + H—I + –
CH3–O–CH3 + I
H
+
Step2 : Nucleophilic attack of I– : I– + CH3–O–CH3 CH3I + CH3OH
10. Write equations of the following reactions :
(i) Friedel-Crafts reaction-alkylation of anisole.
(ii) Nitration of anisole.
(iii) Bromination of anisole in ethanoic acid medium.
(iv) Friedel-Craft's acetylation of anisole.
OCH3 OCH3 OCH3
Anhyd AlCl3 CH3
Ans. (i) + CH 3Cl
CS 2 +
CH3
Anisole 4-Methoxytoluene 2-Methoxytoluene
(Major) (Minor)
OCH3 OCH3 OCH3
H 2SO 4 NO2
(ii) HNO 3
+
NO2
Anisole 2-Nitroanisole 4-Nitroanisole
(Minor) (Major)
OCH3 OCH3 OCH3
Br2 in Br
(iii) Ethanoic acid
+
Br
Anisole p-Bromoanisole o-Nitroanisole
(Major) (Minor)
OCH3 OCH3 OCH3
Anhyd AlCl3 COCH3
(iv) + CH 3COCl +
COCH3
Anisole Ethanoyl chloride 2-Methoxy- 4-Methoxy-
acetophenone acetophenone
(Minor) (Major)

38 Chemistry
11. Show how would you synthesise the following alcohols from appropriate alkenes?
CH3
OH OH
(i) (ii)
OH
OH
(iii) (iv)
CH3 CH2
Ans. (i) or
1-Methylcyclohexene Methylenecyclohexene
(ii)
4-Methylhept-3-ene
(iii) or
Pent-1-ene Pent-2-ene
(iv)
2-Cyclohexylbut-2-ene
12. When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place :
Br
HBr
CH3–CH–CH–CH3 CH3–C–CH2–CH3
CH3 OH CH3
Give a mechanism for this reaction.
Ans. The mechanism of the given reaction involves the following steps :
Step 1 : Protonation
+
H
CH3–CH–CH–CH3 CH3–CH–CH–CH3
CH3 OH CH3 OH2
+
3-Methylbutan-2-ol
Step 2 : Formation of 2° carbocation by the elimination of a water molecule

+
CH3–CH–CH–CH3 CH3–CH–CH–CH3 node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
–H2O
CH3 O+H2 CH3
2°Carbocation
Step 3 : Re-arrangement by the hydride-ion shift.

H
+ 1-2-hydride shilt +
CH3–C–CH–CH3 CH3–C–CH2–CH3
CH3 CH3
3°Carbocation
(more stable)
Step 4 : Nucleophilic attack

Br
+
CH3–C–CH2–CH3 Br— CH3–C–CH2–CH3
CH3 CH3
2-Bromo-2-methylbutane

CBSE 39
CH = CH – CH 2 – OH
13. Write the IUPAC name of the following compound :
Ans. 3-phenyl-prop-2-en-1-ol
14. (a) Arrange the following compounds in the increasing order of their acid strength :
p-cresol, p-nitrophenol, phenol
(b) Write the mechanism (using curved arrow notation) of the following reaction :
H3O
CH2 = CH2 CH3 – + H2O
Ans. (a) p-cresol < Phenol < p-nitrophenol
H H
+
(b) C=C +H–O –H
+
– C – C + H 2O
15. Write the structures of the products when Butan-2-ol reacts with the following :
(i) CrO3 (ii) SOCl2
O Cl
Ans. (i) H3C (ii) H C
CH3 3 CH3
16. Give reasons for the followings :

(a) Acetylation of aniline reduces its activation effect.
(b) CH3NH2 is more basic than C6H5NH2
(c) Although –NH2 is o/p directing group, yet aniline on nitration gives a significant amount of
m-nitroaniline.
Ans. (i) Due to the resonance, the electron pair of nitrogen atom gets delocalised towards carbonyl
group/ resonating structures.
(ii) Because of +I effect in methylamine electron density at nitrogen increases whereas in

aniline resonance takes place and electron density on nitrogen decreases / resonating
structures.
(iii) Due to protonation of aniline/formation of anilinium ion
17. Write the chemical equations involved in the following reactions:
(i) Kolbe's reaction (ii) Friedal- Crafts acetylation of anisole.
OH ONa OH OCH3 OCH3 OH
COOH COCH 3
(i) CO2
Ans. (i) NaOH
(ii) H
+
(ii) +CH 3COCl
Anhyd. AlCl3
+
2-Hydroxybenzoic acid
(Salicylic acid) COCH3

40 Chemistry
18. How do you convert :
(i) Phenol to toluene (ii) Formaldehyde to Ethanol

OH CH3
Ans. (i) Anhyd. AlCl3
+Zn
CH3Cl
H2O/H +
(ii) HCHO+CH3MgX CH3CH 2OMgX CH3CH2OH
19. Give reasons for the following:

(a) Protonation of Phenols is difficult whereas ethanol easily undergoes protonation.
(b) Boiling point of ethanol is higher than that of dimethyl ether.
(c) Anisole on reaction with HI gives phenol and CH3–I as main products and not iodobenzene
and CH3OH.
Ans. (a) In phenols lone pair of electron on oxygen are delocalized over benzene ring due to resonance
but in alcohol lone pair of electron on oxygen are localized & hence available for protonation
/ + R- effect in phenol but not in ethanol.
(b) Due to intermolecular hydrogen bonding
(c) Weaker (O-CH3) bond and stronger(O-C6H5) bond ,due to resonance / carbon in benzene is sp2
hybridized due to which partial double bond character.
20. Write the IUPAC name of the given compound :
CH3
CH3 C CH2 OH
CH3
Ans. 2, 2–Dimethylpropan–1–ol
21. Give reasons for the following :
(i) p-nitrophenol is more acidic than p-methylphenol.
(ii) Bond length of C – O bond in phenol is shorter than that in methanol.
(iii) (CH3)3C – Br on reaction with sodium methoxide (Na+ –OCH3). Gives alkene as the main
product and not an ether.
Ans. (i) Due to withdrawing effect of –NO2 group & donating effect of –CH3 group or
4-nitrophenoxide ion is more stable than 4-methylphenoxide ion
(ii) Due to +R effect of – OH group in phenol / due to sp2 hybridization of C–atom in C–OH
group in phenol whereas sp3 hybridization of C–atom in C–OH group in methanol.
(ii) Williamon’s synthesis is not applicable for tertiary alkyl halides as they yield alkenes instead
of ethers. The reaction of CH3ONa with (CH3)3C–Br gives exclusively 2–methyl propene.
CH3
: :
CH3 – C – Br + Na – O – CH3 CH3 – C = CH 2 + NaBr

CH3 CH3

CBSE 41
EXERCISE-3 RACE
Type 1 : Passage question 1 :
In phenol –OH group directly attached to sp2 hybridised carbon of benzene ring acts as a electron
withdrawing group and is responsible for the acidic nature of phenol. Due to this, the lone pair of
electrons of are involved in resonance with C-atoms of benzine ring. As a result of resonance,
the oxygen atom acquires a partial positive charge. This weakens the –OH bond and thus
facilitates the release of a proton.
(a) Which one is stronger acid
(i) phenol (ii) alcohol (iii) Cresol (iv) None of these
(b) Phenol can be distinguished from ethanol by the reactions with _________.
(i) Br2/CS2 (ii) Na (iii) Neutral FeCl3 (iv) All the above
(c) Which of the following reactions will not give phenol ?
Cl
fusion with NaOH at 300 atm

(i) +
(ii) H 2O / H
NH2
(i) NaNO 2 / HCl

(ii)
(ii) H 2O (Warming)
(i) Oleum
(iii) (ii) NaOH (heating)
+
(iii) H
Cl
(i) NaOH (aq.) / 298 k / 1atm

(iv) (ii) HCl
CH 3
|
(d) The correct IUPAC name of CH3 C CH 2 CH 3 is :
|
OH
(i) tert-butyl alcohol (ii) 2,2-Dimethylpropanol
(iii) 2-Methylbutan-2-ol (iv) 3-Methylbutan-3-ol

42 Chemistry
Question 2 to 6 :- Note :- In the following questions a statement of assertion followed by a reason .
2. Assertion : p-nitrophenol is more acidic than phenol.
Reason : Nitro group helps in the stabilisation of the phenoxide ion by dispersal of negative
charge due to resonance
3. Assertion : Boiling points of alcohols and ethers are high.
Reason : They can form intermolecular hydrogen-bonding.
4. Assertion : Ethanol is a weaker acid than phenol.
Reason : Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH.
5. Assertion : Phenol forms 2, 4, 6 – tribromophenol on treatment with Br2 in carbon disulphide at
Reason : Bromine polarises in H2O.
6. Assertion : Phenols give o- and p-nitrophenol on nitration with conc. HNO3 and H2SO4 mixture.
Reason : –OH group in phenol is o–, p– directing.
Type 3 : Multiple choice Question (one correct answer) (Questions 7 to 16) :- node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
7. Alkene is obtained when an alcohol is passed over heated Cu. The alcohol is:
(i) CH3–CH2–OH (ii) CH3–CH–OH

CH3
CH3 CH3
(iii) CH 3–C–OH (iv) C6H 5–CH–CH 2–OH
CH3
8. What is the correct order of reactivity of alcohols in the following reaction ?
ZnCl2
R–OH + HCl R–Cl + H2O
(i) 1° > 2° > 3° (ii) 1° < 2° > 3° (iii) 3° > 2° > 1° (iv) 3° > 1° > 2°

CBSE 43
9. Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields.
(i) o-Cresol (ii) m-Cresol
(iii) 2, 4-Dihydroxytoluene (iv) Benzyl alcohol
10. CH3CH2OH can be converted into CH3CHO by ________.
(i) catalytic hydrogenation
(ii) treatment with LiAlH4
(iii) treatment with pyridinium chlorochromate
(iv) treatment with KMnO4
11. The process of converting alkyl halides into alcohols involves ___________.
(i) addition reaction (ii) substitution reaction
(iii) dehydrohalogenation reaction (iv) rearrangement reaction
12. IUPAC name of m-cresol is ___________.
(i) 3-methylphenol (ii) 3-chlorophenol
(iii) 3-methoxyphenol (iv) benzene-1,3-diol
13. Which of the following species can act as the strongest base?
(i) OH (ii) OR (iii) OC6H5 (iv) O
NO2
14. Which of the following compounds will react with sodium hydroxide solution in water?
(i) C6H5OH (ii) C6H5CH2OH (iii) (CH3)3COH (iv) C2H5OH
15. Which of the following is most acidic?
(i) Benzyl alcohol (ii) Cyclohexanol (iii) Phenol (iv) m-Chlorophenol
16. Which of the following reagents can not be used to oxidise primary alcohols to aldehydes?
(i) CrO3 in anhydrous medium

(ii) KMnO4 in acidic medium
(iii) Pyridinium chlorochromate
(iv) Heat in the presence of Cu at 573K
ANSWER KEY
Q.No. 1(a) (b) (c) (d) 2 3 4 5 6 7 8
Ans. (i) (iii) (iv) (iii) (i) (i) (ii) (iv) (i) (iii) (iii)
Q.No. 9 10 11 12 13 14 15 16
Ans. (iv) (i),(iii) (ii) (i) (ii) (i) (iv) (iii), (iv)

44 Chemistry
1. The C–O–C bond angle in the ether molecule is : [Term-I _2021-2022]
(a) 101° (b) 90° (c) 120° (d) 180º
Ans. (a)
2. Which of the following reagents will not convert ethyl alcohol into ethyl chloride ?
[Term-I _2021-2022]
(a) PCl5 (b) NaCl (c) SOCl2 (d) HCl/ZnCl2
Ans. (b)
3. Phenol on being heated with concentrated H2SO4 and then with concentrated HNO3 gives :
(a) o-nitrophenol (b) 2,4,6-trinitrophenol [Term-I _2021-2022]
(c) p-nitrophenol (d) m-nitrophenol
Ans. (b)
4. Lucas reagent produces cloudiness immediately with : [Term-I _2021-2022]
CH3
(a) CH3–C–CH3 (b) CH3–CH–CH2–CH3
OH OH
(c) CH3–CH2–CH2–OH (d) CH3–CH–CH2–OH

CH3
Ans. (a)
5. Major products formed by heating (CH3)3C–O–CH2–CH3 with HI are: [Term-I _2021-2022]
(a) (CH3)3C–I and CH3CH2OH (b) (CH3)3C–OH and CH3CH2I
(c) (CH3)3C–I and CH3CH2I (d) (CH3)3C–OH and CH3CH2OH
Ans. (a)
6. A compound (X) with the molecular formula C3H8O can be oxidised is another compound (Y)
whose molecular formula is C3H6O2. The compound (X) may be: [Term-I _2021-2022] node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
(a) CH3–CH2–OCH3 (b) CH3–CH–CH3

OH
(c) CH3–CH2–CH2–OH (d) CH3–CH2–CHO

Ans. (c)
Mg H2O
7. In the following reaction: CH 3 Br dry ether
X Y [Term-1 _2021-2022]
'Y' will be :
(a) CH4 (b) CH3MgBr (c) CH3–OH (d) CH3–CH3
Ans. (a)

CBSE 45
8. Arrange the following compounds in decreasing order of their acidic character :
[Term-1 _2021-2022]
OH OH OH
CH3 NO2
(I) (II) (III)
(a) II > I > III (b) II > III > I (c) III > I > II (d) I > II > III
Ans. (b)
9. Match the following : [Term-1 _2021-2022]
I II
(i) Salicyl aldehyde (A) Kolbe's reaction
(ii) o-nitrophenol (B) Williamson's synthesis
(iii) Salicylic acid (C) Intramolecular Hydrogen bonding
(iv) p-nitrophenol (D) Reimer-Tiemann reaction
(v) Unsymmetrical ether
Which of the following is the best matched option ?

(a) i-A, ii-C, iii-D, iv-B (b) i-D, v-B, iii-C, iv-A
(c) i-D, v-B, ii-C, iii-A (d) i-B, ii-C, iii-A, iv-D
Ans. (c)
10. Which of the following intermediates is formed in the reaction shown below ?
CH3 – CH2 – OH + HI CH3 – CH2 – I + H2O [Term-1 _2021-2022]
(a) CH3CH2 OH2 (b) CH3 CH 2

(c) Both CH3CH2 OH2 and CH3 CH 2 (d) CH3CH2 O CH2 CH3
Ans. (c)
+ – + H
CH3– CH2– O – H + H– I CH3– CH2– O +I
H
+
CH3– CH2 + H2 O
CH3 CH3 I CH3 CH2 I

46 Chemistry
11. The reaction : [Term-1 _2021-2022]
OH OH
1. CHCl3 + NaOH(aq) CHO
+
2. H3O
is an example of
(a) Reimer-Tiemann reaction (b) Kolbe's reaction
(c) Williamson's synthesis (d) Wurtz reaction
Ans. (a) Reimer Tiemann (formylation) Rxn
OH OH
H OH
KOH CH
+ Cl–CH Cl + OH
Cl KOH –HCl
–2KCl
–H2O
OH O
C–H
Salicyl aldehyde
B2H6
12. In the following reaction : PhCH = CH2 – (?) [Term-1 _2021-2022]
H2O2/OH
(Where Ph is Phenyl)
The product formed is :
(a) PhCH–CH3 (b) PhCH2 – CH2 – OH
OH
(c) PhCH2CHO (d) Ph–C–CH3
O
Ans. (b) Ph CH = CH2 + B2H6 (Ph–CH2–CH2–)3B H 2 O 2 / NaOH
3Ph–CH2–CH2–OH node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
13. Phenol is more acidic than ethanol because : [Term-1 _2021-2022]

(a) Ethoxide ion is more stable than Phenoxide ion
(b) Phenoxide ion is more stable than Ethoxide ion
(c) Phenol undergoes electrophilic substitution reaction.
(d) Phenol undergoes protonation easily.
Ans. (b)
O
Due to resonance phenoxide ion is more stable and availability of H+ ion increases. While
RO– do not shows resonance and it is re-combine with H+ ion and availability of H+ decreases.

CBSE 47
14. The structure(s) of the major product (s) expected from the mononitration of 3-methylphenol will
be : [Term-1 _2021-2022]
OH OH OH OH
O2N NO2
and and
(a) (b)
CH3 CH3 CH3
CH3 NO2
NO2
OH OH
OH OH NO2
NO2 and
(c) O2N (d)
and O2N CH3 CH3
CH3 CH3
OH OH OH
dil. HNO3 NO2
Ans. (a) +
CH3 CH3 CH3
NO2
15. 1-Phenylethanol may be prepared by the reaction of C6H5MgBr with : [Term-1 _2021-2022]
(a) CH3–C– CH3 (b) CH3–CHO (c) HCHO (d) CH3–CH2–CHO
O
Ans. (b)
H3 C H3C + – H3C
C6H5 MgBr + C=O C–O C – OMgBr
H H H
C6H5
+ H2O
CH3–CH–OH H3C Br
C6H5 C–OH + Mg
H OH
1-Phenyl Ethanol C6H5
16. Which reagent will be required for one step conversion of benzenediazonium chloride to phenol ?
(a) Cu2Cl2 (b) NaOH(aq) [CBSETerm-1 _2021-2022]
(c) H2O (d) Alcoholic KOH
Ans. (c)
+
N2 Cl OH
–
H2O
warm + N2 + HCl
+ –
N2 Cl OH
+H2O + N2 + HCl

48 Chemistry
17. Write the structure of the main products formed in the following reactions: [1 × 3 = 3]
O
CH2–C–O–CH3 NaBH4
(a) [CBSE Compartment_2021]
O
+
H2O, H
(b) HCHO + CH3MgBr
CH3 +
H2O, H
(c)
OR
(a) Carry out the following conversions : [1 × 2 = 2]
(i) Propene to propan-2-ol
(ii) Benzyl chloride to benzyl alcohol
(b) Arrange the following compounds in increasing order of their acidic strength : [1]
4-Methylphenol, Phenol, 4-Nitrophenol
OH
CH2–C–OCH3
Ans. (i)
O
(ii) CH3CH2–OH
CH3
(iii) OH
OR
(a) (i) CH2=CH–CH3 H Br
CH3-CH-CH3 aq KOH
CH3-CH-CH3
Br node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
OH
Propan-2-ol
O
C–Cl CHO CH2–OH
H2 LiAlH4
(ii) BaSO4,Pd 2H
OH OH OH
(b) < <
CH3 NO2

CBSE 49
18. (a) Out of t-butyl alcohol and n-butanol, which one will undergo acid catalyzed dehydration
faster and why ? (CBSE 2020)
(b) Carry out the following conversions : [1×3=3]
(i) Phenol to salicylaldehyde
(ii) t-butylchloride to t-butyl ethyl ether
(iii) Propene to Propanol
OR
(a) Give the mechanism for the formation of ethanol from ethene. [2]
(b) Predict the reagent for carrying out the following coversions : [1×3=3]
(i) Phenol to benzoquinone
(ii) Anisole to p-bromoanisole
(iii) Phenol to 2,4,6-tribromophenol
Ans. (a) Tert-butyl alcohol, because it forms more stable 3º carbocation than 1º carbocation.
(b)
OH
OH OH OH CHO
H Cl NaOH CH –H2O
(i) + Cl – CH + OH
Cl NaOH – HCl
– 2NaCl Salicyaldehyde
C2H 5Cl
(ii) (CH3)3CCl + NaOH (aq) (CH3)3COH (CH3)3CONa (CH3)3COC2H5
B2 H6 (3NaOH + 3H 2O 2)
(iii) CH3CH = CH2 (CH3 – CH2 – CH2 –)3B CH3 – CH 2 – CH3
|
OH
OR
(a) Step 1 : Protonation of alkene to form carbocation by electrophilic attack of H3O+.
H2O + H+ H3O+
H H
|+ | ..
C=C +H–O
.. – H –C–C + + H2 O
..
|
Step 2 : Nucleophilic attack of water on carbocation
H H H
| .. | | |+
–C–C+ +H2O
.. –C–C–O –H
| | |
Step 3 : Deprotonation to form an alcohol.
..
H H H :OH
| | | | |
+
–C–C–O –H – C – C – + H+
| | | |
(b) (i) (K2Cr2O7 + H2SO4) (Na2Cr2O7 + H2SO4)
(ii) Br2 in CH3COOH
(iii) Br2 aq./Bromine water

50 Chemistry
19. (a) Give equations of the following reactions : [5]
(i) Phenol is treated with conc. HNO3.
(ii) Propene is treated with B2H6 followed by H2O2/OH–. (CBSE 2019)
(iii) Sodium t-butoxide is treated with CH3Cl.
(b) How will you distinguish between butan-1-ol and butan-2-ol ?

(c) Arrange the following in increasing order of acidity :
Phenol, ethanol, water
OR
(a) How can you obtain Phenol from :
(i) Cumene, (ii) Benzene sulphonic acid, (iii) Benzene diazonium-chloride ?
(b) Write the structure of the major product obtained from dinitration of 3-methylphenol.
(c) Write the reaction involved in Kolbe's reaction. [5]
OH OH
O2N NO2
conc. HNO3
Sol. (a) (i) (picric acid)
NO2
(ii) CH3–CH=CH2+(½B2H6) (CH3–CH2–CH2–)3B
–
H2O 3H2O 2,OH
3CH3–CH2–CH2–OH
CH3 CH3
(iii) CH3–C–ONa + CH3Cl CH3–C–O–CH3
CH3 CH3
(b) On heating with (NaOH + l2), Butan-2-ol forms yellow ppt of iodoform (CH4) whereas
butan-1-ol does not (or any other correct chemical test)
(c) Ethanol < Water < Phenol
OR
CH3 CH 3
CH2–CH CH3–C–O–O–H OH
(a) (i) O2 +
H
+ CH3COCH3
H 2O
SO 3H OH
(ii) (i) NaOH node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
+
(ii) H
+ –
N2Cl OH
(iii) H2 O
+N2+HCl
OH
O2N
(b)
CH3
NO2
OH ONa OH
COOH
NaOH (i) CO2
(c) (ii) H
+
(Salicylic acid)

CBSE 51
20. Write the IUPAC name of the following : (CBSE 2018)
CH3
CH3 – C – CH – CH3
C2H5 OH
Ans.
21. Write the structures of the main products in the following reactions : (CBSE 2018)
O OC2H 5
NaBH4
CH2–C–OCH 3 CH = CH2
+
(i) (ii) H (iii)
O + H2 O + HI
OH
NaBH
CH2—C—OCH3
Ans. (i)
O
CH–CH3
(ii)
OH
(iii)

52 Chemistry

1. Write the IUPAC name of the following compound : [1]
CH = CH – CH 2 – OH
2. Write the structure of the major product obtained from dinitration of 3-methylphenol. [1]
3. How would you convert following: [1]
Phenol to benzoquinone
4. Boiling point of ethanol is higher than that of dimethyl ether. Why ? [2]
5. Anisole on reaction with HI gives phenol and CH3–I as main products and not iodobenzene and
CH3OH. Why ? [2]
6. Explain the following observations : [2]
(i) Phenol is more acidic than ethanol.
(ii) o– and p-nitrophenols are more acidic than phenol.
7. Write the equations involved in the following reactions: [2]
(i) Reimer – Tiemann reaction
(ii) Williamson’s ether synthesis.
8. Explain the mechanism of acid catalysed hydration of an alkene to form corresponding
alcohol. [3]
9. Write the structures of the main products in the following reactions: [3]
O CH = CH 2
NaBH4
CH 2–C–OCH 3 H+
(i) ? (ii) + H2 O ?
O
OC2H 5
(iii) + HI ?
10. How can you obtain Phenol from (i) Cumene, (ii) Benzene sulphonic acid [3]
11. (a) Give equations of the following reactions : [5]
(i) Phenol is treated with conc. HNO3.
(ii) Propene is treated with B2H6 followed by H2O2/OH–.
(iii) Sodium t-butoxide is treated with CH3Cl.
(b) How will you distinguish between butan-1-ol and butan-2-ol ?
(c) Arrange the following in increasing order of acidity :
Phenol, ethanol, water

CBSE 53
MOCK TEST SOLUTIONS

1. 3-phenyl-prop-2-en-1-ol
OH
O2N
2.
CH3
NO2
OH O
3. K2Cr2O7
H2SO4
O
Phenol benzoquinon
4. (a) Due to intermolecular hydrogen bonding.

(b) o-nitrophenol is steam volatile due to intramolecular hydrogen bonding while p-nitrophenol is
less volatile due to intermolecular hydrogen bonding.
5. Weaker (O-CH3) bond and stronger (O-C6H5) bond ,due to resonance / carbon in benzene is sp2
hybridized due to which partial double bond character.
6. (i) Since the phenoxide ion left after the removal of a proton is stabilized by resonance where as
alkoxide ion is not which is left after the removal of a proton found alcohol.
(ii) o & p-nitrophenols are more acidic then phenol due to –M effect of NO2 at from o & p
position make the ejections of H+ easity & secondly stabilized the conjugate base.
–+ –+
OH ONa ONa
CHO
7. (i) CHCl3 3+ aq.NaOH
CHCl+ aq.NaOH CHCl2 NaOH
Intermediate H+
OH
CHO
Salicylaldehyde
(ii) Williamson ether synthesis is a laboratory method to prepare symmetrical and unsymmetrical
ethers by allowing alkyl halides to react with sodium alkoxides.
R – X + R' – O Na R – O – R' + NaX

Alkyl halide Sodium alkoxide Ether
This reaction involves SN2 attack of the alkoxide ion on the alkyl halide. Better results are
obtained in case of primary alkyl halides.
CH3 CH3
– +
CH–CH–
3 O Na + CH3 – Br CH–
3 O–CH–CH 3 + NaBr
If the alkyl halide is secondary or tertiary, then elimination competes over substitution.

54 Chemistry
8. Step I : Protonation of alkene to form carbocation by electrophilic attack of H3O+.
H2O + H+ H3O+
H H
+ +
C=C + H–O–H –C–C + H2O
Step II : Nucleophilic attack of water on carbacation.

H H H
+ +
–C–C + H 2O –C–C–O–H
Step III : Deprotonation to form an alcohol.

H H H OH
+
–C–C–O—H + H2O –C—C– + H3O+
CH2–C–OCH3
9. (i)
O
CH–CH3
(ii) OH
OH
(iii) + C2H5–I
CH3 CH3
CH–CH
2 CH–C–O–O–H
3 OH SO3H OH
O2 H
+ (i) NaOH
10. (i) H 2O
+CH2 COCH 3 (ii) (ii) H
+
OH OH
O2 N NO2
conc. HNO 3
11. (a) (i)
NO2
(ii) CH3–CH=CH2+(H–BH2)2 (CH3–CH2–CH3)3B

H2O 3H2O2,OH¯ node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\11_Alcohol, Phenol & Ether
3CH3–CH2–CH2–OH
CH3 CH3
(iii) CH–C–ONa
3 + CH3Cl CH–C–O–CH
3 3
CH3 CH3
(b) On heating with NaOH/I2, Butan-2-ol forms yellow ppt of iodoform (CH4) whereas butan-1-ol
does not (or any other correct chemical test)
(c) Ethanol < Water < Phenol

CBSE 55
ALDEHYDE, KETONES AND CARBOXYLIC ACID : CHAPTER-12

CHAPTER AT A GLANCE
Topic : Carbonyl compounds : Aldehydes, Ketones
Carbonyl group : C=O group is known as carbonyl group.
Carbonyl compounds : The carbonyl compounds in which C=O (carbonyl group) is present,
known as carbonyl compounds.
R R
• Aldehyde C=O and Ketone C=O are carbonyl compounds.
H R
• General homologous series formula of carbonyl compound is CnH2nO.
n = 1, 2, 3........... for Aldehyde
n = 3, 4, 5 .......... for Ketones
• Orbital diagram of carbonyl group : C == O
-bond sp2 120°

sp2 -bond sp2
C O C O C O
sp 2 sp2 sp2
120°
• Polar nature of carbonyl group

O O–
+
C C
(A) (B)
• Naming of carbonyl compounds
Br O
CHO
CH3CHO
H 3C CH CH3 C H
Acetaldehyde Benzaldehyde
-Bromobutraldehyde
O O O O
node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\12_Aldehydes, Ketones and Carboxylic acids
C C CH3 C
CH3 C CH3 CH3 CH2
Acetone Acetophenone Propiophenone Benzophenone
O Br CH3 O
CH3 C H CH3 CH2 CH2 CH CH CH2 C H
4-Bromo-3-methylheptanal
Ethanal
O
CHO
CH3 Cyclohexanecarbaldehyde
3-Methylcyclopentanone

56 Chemistry
O O
CH3 CH2 CH CH C H C CH2 CH3
Pent-2-enal 1-Phenylpropan-1-one
O O CH3 O CH3
H3C CH2 C CH2 C H CH3 CH C CH CH3
3-Oxopentanal 2,4-Dimethylpentan-3-one
CHO
OHC CH3 CH CH2 CHO
CHO
Propane-1,2,3-triacarbaldehyde
NO2
4-Nitrobenzenecarbaldehyde
or
4-Nitrobenzaldehyde
General Methods of Preparations of Carbonyl compounds

Structure Common name IUPAC name
HCOOH Formic acid Methanoic acid
CH3COOH Acetic acid Ethanoic acid
CH3CH2COOH Propionic acid Propanoic acid
CH3CH2CH2COOH Butyric acid Butanoic acid
(CH3) 2CHCOOH Isobutyric acid 2-Methylpropanoic acid
HOOC COOH Oxalic acid Ethanedioic acid
HOOC CH 2 COOH Malonic acid Propanedioic acid
HOOC (CH2) 2 COOH Succinic acid Butanedioic acid
HOOC (CH2) 3 COOH Glutaric acid Pentanedioic acid
HOOC (CH2) 4 COOH Adipic acid Hexanedioic acid
HOOC CH 2 CH(COOH) CH 2 COOH – Propane-1, 2, 3-tricarboxylic
acid
COOH
Benzoic acid Benzenecarboxylic acid
(Benzoic acid)

CH2COOH
Phenylacetic acid 2-Phenylethanoic acid
COOH
Phthalic acid Benzene-1, 2-dicarboxylic
COOH acid
(I) The methods by which aldehydes and ketones both are formed :
(1) By oxidation of alcohols
(2) By catalytic dehydrogenation of alcohol
(3) By ozonolysis of alkene
(4) By Hydration of alkyne
(II) The methods by which only aldehdyes are formed.
(1) By reduction of acid chloride (Rosenmund reaction)
(2) From nitrile and esters (stephen reaction)
(III) The methods by which only ketone are formed.
(1) By Grignard reagent

CBSE 57
General Methods of Preparations of Aromatic aldehyde
I. By Gattermann Koch Synthesis reaction
2. By Alkyl benzene
(a) Etard reaction
(b) By Chlorination of alkyl benzene followed by hydrolysis.
General methods of Preparation of Aromatic Ketone
Chemical reactions of Carbonyl compounds
I. Nucleophilic addition reactions (NAR)
Nu Nu Nu
a + –
C O step 1 a H+ fast a
b slow b O step 2 b OH
Planar Tetrahedral intermediate Addition product
2. Nucleophilic addition Elimination reactions

OH
C O + H 2N Z C C N Z + H2O
NHZ
Z = Alkyl, aryl, OH, NH 2, C6H5NH, NHCONH 2, etc.
3. Reduction reactions
4. Oxidation reactions
5. Aldol reaction due to -hydrogen
6. Other reactions –
(i) Cannizzaro reaction
(ii) Halogenation
General Methods of Preparations of Aliphatic and Aromatic Carboxylic acid
I. Oxidation of primary alcohols
2. By Alkyl benzene
3. By Nitrile and acid amide
4. By Grignard reagents
5. By Acid halide and acid anhydride

6. By Esters

58 Chemistry
Chemical properties of Carboxylic acid
(I) Reaction involving cleavage of —O —H bond.
(1) Acidity (Reaction with metals and alkalines)
+
2R COOH + 2Na 2R COONa + H 2
Sodium carboxylate
O
||
(II) Reaction involving cleavage of —C —OH bond
(1) Formation of anhydride
(2) Esterification
(3) Reaction with PCl3, PCl5, SOCl2
O O
|| ||
(III) Reaction involving —C — OH group of reaction involving R — C — OH cleavage.
(1) Reduction
(2) Decarboxylation
O
||
(IV) Reaction involving alkyl group (–R) of R – C – OH
(1) Halogenation
Name Reactions
I. Rosenmund reduction
2. Stephen reaction
3. Etard reaction
4. Gattermann-Koch aldehyde synthesis reaction

5. Clemmensen reduction
6. Wolff-Kishner reduction
7. Friedal Craft acylation of benzene
8. Aldol condensation
9. Cannizzaro reaction
10. Kolbe electrolysis
11. Hell-Volhard-Zelinsky reaction
Distinguish between pair of compounds by Chemical Test
* Organic Reasoning
* Inter conversion

CBSE 59

1. Write the structures of the following compounds.
(i) -Methoxypropionaldehyde (ii) 3-Hydroxybutanal
(iii) 2-Hydroxycyclopentane carbaldehyde (iv) 4-Oxopentanal
(v) Di-sec. butyl ketone (vi) 4-Fluoroacetophenone
H3CO O
Ans. (i) H3C–CH–C–H
OH O
(ii) H3C – CH – CH2 – C –H
(iii) CHO
OH
O
(iv) CH3 –C–CH2 – CH2 –CHO
CH3 O CH3
(v) CH3CH2 CH–C–CH–CH2CH3
O
(vi) F C–CH3
2. Write the structures of products of the following reactions :

O
C Anhyd. AlCl3
(i) C2H5 Cl (ii) (C6H5CH2)2Cd + 2CH3COCl
CH3
1 CrO2Cl2
(iii) H3C – C C –H (iv) 2H3O
+
NO2
O
C
Ans. (i)
Anhyd. AlCl
C2H5 + HCl (ii)
ethyl phenylketone
O OCrCl OH
Tautomerises HO
(iii) H3C – C – CH3 (iv) O2N CHO
Propanone OCrCl OH
p - Nitrobenzaldehyde
3. Arrange the following compounds in increasing order of their boiling points.

CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3
Ans. CH3CH2 CH3 CH3OCH3 CH3 CHO CH3 CH2OH
non polar more polar H bond i ng

60 Chemistry
4. Arrange the following compounds in increasing order of their reactivity in nucleophilic addition
reactions.
(i) Enthanal, Propanal, Propanone, Butanone.
(ii) Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.
Hint : Consider steric effect and electronic effect.
1
Ans. Reactivity of carbonyl compound (+)ve charge on sp2 C steric hindrence
O O O O
C C C C
(i) CH3 H CH3CH2 H CH3 CH3 CH3 CH2CH3
Ethanal Propanal Propanone Butanone
The +I effect of the alkyl group increases in the order :

Ethanal < Propanal < Propanone < Butanone
If +I effect increases then (+)ve charge on sp2 C decreases.
So reactivity order is :
Butanone < Propanone < Propanal < Ethanal
O
CHO CH3 CHO
C
(ii) CH3
NO2 CHO
p-Nitrobenzaldehyde p-Tolualdehyde Benzaldehyde Acetophenone
more – I less – I +I of –CH3
–I group on > C = O inreases (+)ve charge so reactivity order is

Acetophenone < p-tolualdehyde < Benzaldehyde < p-Nitrobenzaldehyde
5. Predict the product of the following reactions :
O O2N
O
(i) (ii)
+
+ HO – NH2
H + NH2 – NH NO2

O
O C
H+ H
+
(iii) R – CH = CH – CHO + NH2 – C – NH – NH2 (iv) CH3

+ CH3CH2NH2
N–OH
Ans. H(i)
+
O2N
NNH NO2
NO (ii)
O
+
H
(iii) R – CH = CH – CH = N – NH – C – NH 2
O H3C
C C = N – CH2CH3
(iv)

CBSE 61
6. Show how each of the following compounds can be converted to benzoic acid.
(i) Ethylbenzene
(ii) Acetophenone
(iii) Bromobenzene
(iv) Phenylethene (Styrene)
CH2CH3 COOK COOH
+
KMnO 4 – KOH H3O
Ans. (i)
Ethylbenzene Benzoic acid
COCH3 COOK COOH

+
KMnO 4 – KOH H3O
(ii)
Acetophenone Benzoic acid
O
Br MgBr C COOH
Mg O=C=O H 3O
+
(iii) OMgBr
Ether dry ice
Bromobenzene Benzoic acid
CH=CH2 COOK
+ COOH
KMnO 4 – KOH H 3O
(iv) + HCOOK
Phenylethene
(styrene)
7. Which acid of each pair shown here would you expect to be stronger?
(i) CH3CO2H or CH2FCO2H (ii) CH2FCO2H or CH2ClCO2H
(iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H
(iv) F3C COOH or H3 C COOH
Ans. Acidic strength

(i) CH3CO2 H < CH2FCO2H (ii) CH2F CO2H > CH2ClCO2H
(iii) CH2FCH2CH2COH < CH3CHFCH2CO2H (iv) F3C
COOH > H3C COOH
8. Give names of the reagents to bring about the following transformations :

(i) Hexan-1-ol to hexanal
(ii) Cyclohexanol to cyclohexanone
(iii) p-Fluorotoluene to p-fluorobenzaldehyde
(iv) Ethanenitrile to ethanal
(v) Allyl alcohol to propenal
(vi) But-2-ene to ethanal
Ans. (i) C5H5NH+ CrO3Cl–(PCC)
(ii) K2Cr2O7 in acidic medium
(iii) CrO3 in the presence of acetic anhydride/1. CrO2Cl2 2. HOH
(iv) (Diisobutyl) aluminium hydride (DIBAL-H)
(v) PCC
(vi) O3/H2O-Zn dust

62 Chemistry
9. Arrange the following compounds in the increasing order of their boiling points :
CH3CH2CH2CHO, CH3CH2CH2CH2OH, H5C2–O–C2H5, CH3CH2CH2CH2CH3
Ans. CH3CH2CH2CH2CH3 < H5C2 – O – C2H5 < CH3CH2CH2CHO < CH3CH2CH2CH2OH
10. Would you expect benzaldehyde to be more reactive or less reactive in nucleophilic addition
reactions than propanal ? Explain your answer.
Ans. The carbon atom of the carbonyl group of benzaldehyde is less electrophilic than carbon atom of
the carbonyl group present in propanal. The polarity of the carbonyl group is reduced in
benzaldehyde due to resonance as shown below and hence it is less reactive than propanal.
11. An organic compound (A) with molecular formula C8H8O forms an orange-red precipitate with 2,4-
DNP reagent and gives yellow precipitate on heating with iodine in the presence of sodium
hydroxide. It neither reduces Tollens' or Fehlings' reagent, nor does it decolourise bromine water or
Baeyer's reagent. On drastic oxidation with chromic acid, it gives a carboxylic acid (B) having
molecular formula C7H6O2. Identify the compounds (A) and (B) and explain the reactions involved.
O
O 2N O2 N
Ans. C H 3C
CH 3 + H 2NHN NO 2 –H2O
C N NH NO2
(A)
C 8H 8O 2,4-Dinitrophenylhydrazine 2,4-DNP derivative
12. Write chemical reactions to affect the following transformations:
(i) Butan-1-ol to butanoic acid
(ii) Benzyl alcohol to phenylethanoic acid
(iii) 3-Nitrobromobenzene to 3-nitrobenzoic acid
(iv) 4-Methylacetophenone to benzene-1,4-dicarboxylic acid
(v) Cyclohexene to hexane-1,6-dioic acid
(vi) Butanal to butanoic acid.
Ans. (i) CH3CH2CH2CH2OH CrO H SO
Jones reagent
CH3CH2CH2COOH
3 2 4
Butan-1-ol Butanoic acid

(ii) C6H5CH2OH HBr
C6H5CH2Br KCN C6H5CH2CN H 2O
C6H5CH2COOH

O O
+
Mg CO2 H3O
(iii) Br ether
MgBr (dry ice)
C C
OMgBr OH
O2 N O2 N O2 N O 2N
3-Nitrobromobenzene 3-Nitrobenzoic acid
COCH COOK COOH
KMnO4/KOH dil. H2SO4
(iv) H3C KOOC HOOC

4-Methylacetophenone Dipotassium benzene- Benzene-1, 4-dicarboxylic
1, 4-dicarboxylate acid (Terephthalic acid)
KMnO 4–H 2SO 4 COOH

(v) COOH
Cyclohexene Hexane-1, 6-dioic acid (Adipic acid)
(iv) CH3CH2CH2CHO Ammoniacal AgNO 3

(Tollens' reagent)
CH3CH2CH2COOH
Butanal Butanoic acid

CBSE 63

1. Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents.
(i) PhMgBr and then H3O+
(ii) Tollen's reagent
(iii) Semicarbazide and weak acid
(iv) Excess ethanol and acid
(v) Zinc amalgam and dilute hydrochloric acid
OMgBr OH
CH=O Ph–MgBr C H H3O
+ C H
Ans. (i) Ph Hydrolysis Ph
Cyclohexane- Cyclohexylphenylcarbinol
carbaldehyde
O
CH=O C–O–
(ii) + 2[Ag(NH3)2] + 3OH
+ –
+ 2Ag + 4NH3 + 2H2O
Silver mirror
Cyclohexane- Cyclohexane-
Tollen's reagent carboxylate ion
carbaldehyde
O
CHO O
CH=NNH–C–NH2 + H2 O
(iii) + H2NNH–C–NH2
Semicarbazide
Cyclohexane- Cyclohexanecarbaldehyde
carbaldehyde semicarbazone
OC2H5
CHO H OC2H5 Dry HCl gas
+ C OC H + H O
(iv) 2 5 2
H
Cyclohexane- H OC2 H5
Ethanol (Excess) Cyclohexanecarbaldehyde
carbaldehyde
diethyl acetal
CH3
CHO Zn/Hg–HCl
(v) (clemmensen
reduction)
Cyclohexane- Methylcyclohexane
carbaldehyde
2. Which of the following compounds would undergo aldol condensation, which the Cannizzaro
reaction and which neither ? Write the structures of the expected products of aldol condensation
and Cannizzaro reaction.
(i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde
(iv) Benzophenone (v) Cyclohexanone (vi) 1-Phenylpropanone
(vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2, 2-Dimethylbutanal
Ans. Aldehydes and ketones having at least one -hydrogen undergo aldol condensation (ii), (v), (vi),
(vii) gives aldol condensation.
Aldehydes (only) having no -hydrogen undergo Cannizzaro reactions. (i), (iii), (ix) gives
cannizzaro reaction.
Compound (iv) is a ketone having no -hydrogen atom and compound (viii) Butan-1-ol is an
alcohol. Hence, these compounds do not undergo either aldol condensation or cannizzaro
reactions.

64 Chemistry
Aldol condensation
CH3
(ii) 2CH3CH2CH2—CH—CHO dil. NaOH CH3CH2CH2—CH—CH—C—CH2CH2CH3
CH3 CH3 OH CHO
2-Methylpentanal
O
(v) 2 O dil NaOH
Cyclohexanone
O CH3
dil NaOH
(vi) 2 C—CH2CH3 C=C—C
CH2 O
1-Phenylpropanone
CH3
CHO
(vii) 2 CH2CHO dil NaOH
CH2—CH=C
Phenylacetaldehyde
Cannizzaro reaction :
H
H H
(i) 2 C=O + conc. KOH H—C—OH + C—OK
H O
H
Methanal Methanol Potassium methanoate
O
(iii) 2 CHO+conc.KOH CH2—OH + C—OK
Benzaldehyde Benzyl alcohol Potassium benzoate
CH3 CH3 CH3

conc.NaOH
(ix) CH3CH2—C—CHO CH3CH2—C—CH2—OH + CH3CH2—C—C—ONa
CH3 CH3 CH3O
2, 2-Dimethylbutanal 2, 2-Dimethylbutan-1-ol Sodium 2, 2-dimethylbutanoate
3. How will you convert ethanal into the following compounds ?

(i) Butane-1, 3-diol (ii) But-2-enal (iii) But-2-enoic acid
OH OH
dil NaOH NaBH4
Ans. (i) CH3CHO CH3—CH—CH2—CHO (Redcution) CH3—CH—CH2—CH2—OH
Ethanal 3-Hydroxybutanal Butane-1, 3 - diol
OH
dil NaOH
(ii) CH3CHO CH3—CH—CH2—CHO –H2O
CH3–CH=CH–CHO
Ethanal 3-Hydroxybutanal But - 2 - enal
(iii) When treated with Tollen's reagent, But-2-enal produced in the above reaction produces
but-2-enoic acid.
+ –
[Ag(NH3)2] OH
CH3–CH=CH–CHO Tollen's reagent
CH3CH=CHCOOH
But-2-enal But-2-enoic acid

CBSE 65
4. Write structural formulas and names of four possible aldol from propanal and butanal. In each
case, indicate which aldehyde acts as nucleophile and which as electrophile.
Ans. (i) Taking two molecules of propanal, one which acts as a nucleophile and the other as an
electrophile.
OH CH3
dil NaOH
2CH3CH2CHO CH3CH2—CH—CH—CHO
Propanal 3-hydroxy - 2 - methylpentanal
(ii) Taking two molecules of butanal, one which acts as a nucleophile and the other as an
electrophile.
OH CH2CH3
dil NaOH
2CH3CH2CH2CHO CH3CH2CH2—CH—CH—CHO
Butanal 2-Ethyl - 3 - hydroxyhexanal
(iii) Taking one molecule each of propanal and butanal in which propanal acts as a nucleophile
and butanal acts as an electrophile.
OH CH3
CH3CH2CH2CHO + CH3CH2CHO CH3CH2CH2—CH—CH—CHO
Butanal Propanal 3-Hydroxy - 2 -methylhexanal
(Electrophile) (Nucleophile)
(iv) Taking one molecule each of propanal and butanal in which propanal acts as an electrophile
and butanal acts as a nucleophile.
OH CH2CH3
CH3CH2CHO + CH3CH2CH2CHO CH3CH2—CH—CHCHO
Propanal Butanal 2-Ethyl - 3 - hydroxypentanal
(Electrophile) (Nucleophile)
5. An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute sulphuric
acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid
produced (B). (C) on dehydration gives but-1-ene. Write equations for the reactions involved.
Ans. Hydrolysis of ester gives acid and alcohol
O O
dil H2SO4
CH3CH2CH2–C–OCH2CH2CH2CH3 CH3CH2CH2–C–OH + CH3CH2CH2CH2OH
Butylbutanoate Butanoic acid Butan-1-ol
(A) (B) (C)
O
CH3CH2CH2–C–OH
CrO3/CH3COOH Butanoic acid
Oxidation (B)
CH3CH2CH2CH2 -OH
Dehydration
–H2O
CH3CH 2CH=CH 2
But-1-ene
(Only 1-Alkanol gives acid on oxidation)

66 Chemistry
6. Arrange the following compounds in increasing order of their property as indicated :
(a) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone
[Reactivity towards HCN]
(b) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH
[Acid strength]
(c) Benzoic acid, 4-Nitrobenzoic acid, 3,4–Dinitrobenzoic acid, 4–Methoxybenzoic acid
[Acid strength]
(d) CH3COCl, CH3CONH2, CH3COOCH3, (CH3CO)2O [Reactivity in hydrolysis]
Ans. (a) Di-tert-butyl ketone < Methyl tert-butyl ketone < Acetone < Acetaldehyde
(b) (CH3)2CHCOOH,< CH3CH2CH2COOH < CH3CH(Br)CH2COOH,< CH3CH2CH(Br)COOH
(c) 4-Methoxybenzoic acid < Benzoic acid < 4-Nitrobenzoic acid < 3, 4-Dinitrobenzoic acid
(d) CH3CONH2 < CH3COOCH3 < (CH3CO)2O < CH3COCl
7. Give simple chemical tests to distinguish between the following pairs of compounds.
(i) Propanal and Propanone (ii) Acetophenone and Benzophenone
(iii) Phenol and Benzoic acid (iv) Benzoic acid and Ethyl benzoate
(v) Pentan-2-one and Pentan-3-one (vi) Benzaldehyde and Acetophenone
(vii) Ethanal and Propanal
Ans. (i) By Tollen's test
(a) Propanal reduces Tollen's reagent, fehling solution, Benedict solution but propanone
(ketone) does not reduces.
(b) Iodoform test :
Propanone CH3–C–CH3 gives iodoform test but propanal (CH3–CH2–CHO) does not.
O
(ii) Acetophenone and Benzophenone can be distinguished using the iodoform test.
Acetophenone gives iodoform test but benzophenone does not.
(iii) Phenol and benzoic acid can be distinguished by ferric chloride test and NaHCO3 test.

(a) Phenol gives voilet colour with FeCl3.
(b) Benzoic acid gives CO2 with NaHCO3 while phenol does not.
(iv) Benzoic acid and Ethyl benzoate can be distinguished by sodium bicarbonate test.
Sodium bicarbonate test :
Benzoic acid react with NaHCO3 to produce brisk effervescence due to the evolution of CO2
gas but ethylbenzoate does not.
(v) Pentan-2-one and pentan-3- one can be distinguished by iodoform test. Pentan-2-one gives
iodoform test but pentan-3-one does not.
(vi) Benzaldehyde and acetophenone can be distinguished by the (a) Tollen's test (b) Iodoform
test. Benzaldehyde gives Tollen's test where as acetophenone gives iodoform test.
(vii) Ethanal and propanal can be distinguished by iodoform test. Ethanal gives iodoform test but
propanal does not.

CBSE 67
8. How will you prepare the following compounds from benzene ? You may use any inorganic
reagent and any organic reagent having not more than one carbon atom
(i) Methylbenzoate (ii) m - Nitrobenzoic acid (iii) p - Nitrobenzoic acid
(iv) Phenylacetic acid (v) p - Nitrobenzaldehyde
CH3 COOH COOCH3
Ans. (i) AlCl3 KMnO4 H
+ CH3–Cl CH 3OH
(ii) In above reaction if

COOH COOH
HNO3
+ H 2SO4
(Nitration) NO2
CH3 CH3 COOH
CH 3Cl/
Anhyd. AlCl3 HNO3/H 2SO4 KMnO4–KOH
(iii) (Friedel-Craft (Nitration) H 3O
+
alkylation)
Benzene NO2 NO2
(Major) p-Nitrobenzoic acid
CH3 CH2Br CH2CN CH2COOH

CH 3Cl/
+
Anhyd.AlCl3 Br2 and hv Alc. KCN, H /H2O
(iv)
Benzene Toluene Benzylbromide Benzylcyanide Phenylacetic aicd
CH3 CH3 CHO

CH 3Cl/
Anhyd.AlCl3 HNO 3/H 2SO 4 CrO3
(v)
Benzene NO2 NO2
p-Nitrobenzaldehyde
9. How will you bring about the following conversions in not more than two steps ?
(i) Proapnone to Propene (ii) Benzoic acid to Benzaldehyde
(iii) Ethanol to 3-Hydroxybutanal (iv) Benzene to m-Nitroacetophenone
(v) Benzaldehyde to Benzophenone (vi) Bromobenzene to 1-Phenylethanol

(vii) Benzaldehyde to 3-Phenylpropan-1-ol
(viii) Benazaldehyde to -Hydroxyphenylacetic acid
O OH
NaBH4 conc.H 2SO 4
Ans. (i) CH3–C–CH3 CH3–CH–CH3 CH3–CH=CH2
Propene
COOH COCl CHO
SOCl2 H2
(ii) Pd–BaSO4
Benzoic acid Benzaldehyde

OH
CrO3 dil.NaOH
(iii) CH3–CH2–OH CH3CHO (Aldol CH3CHCH2CHO
Ethanol condensation) 3-hydroxybutanal
COCH3 COCH3
CH3COCl,
Anhyd AlCl3 HNO 3/H2SO4
(iv) (Friedel-Craft
alkylation) NO2
Benzene

68 Chemistry
O
CHO COOH COCl + Anhyd.AlCl3 C
[O] SOCl2
(v) (Oxidation) (Friedel-Craft acylation)
Benzaldehyde Benzophenone
OH
Br MgBr H3C–CH
Mg/dry ether (i) CH3CHO
(vi) (ii) H 2O
Bromobenzene 1-Phenylethanol
CHO CH=CHCHO CH2CH2CH2OH
(i) NaOH Ni/H2
(vii) (ii)
Benzaldehyde (Aldol condensation) 3-Phenylpropan-1-ol
(viii)
10. Complete each synthesis by giving missing starting material, reagent or products.
(i) (ii)
(iii) (iv)
(v) (vi)
(vii) (viii)
(ix) (x)

(xi)
COOK
COCl
Ans. (i)
KOH, heat (ii) COCl
Pot benzoate
Phthalic acid Phthaloyl chloride
O
(iii) C6H5–CH = N–NH–C–NH2
Benzaldehyde semicarbazone
(iv)
E
76 Chemistry
1. Arrange the following compounds in increasing order of their property as indicated in
bracket : (Any two) (CBSE Term – II_2022)
CH3
(i) CH3–CHO, CH3–C–CH3, CH3–C–C–CH3,
O O CH3
(reactivity towards HCN)
(ii) CCl3–COOH, CF3–COOH, (CH3)3C–COOH

(acid strength)
COOH COOH COOH COOH

NO2
(iii) ; ; ; [1× 2=2]
NO2 NO2 OCH3

(acid strength)
CH3 HC H3C
Ans. (i) CH3–C–C–CH3 < 3 C=0 < C=0 3<2<1
H3C H
O CH3
(ii) (CH3)3CCOOH < CCl3COOH < CCl3COOH < CF3COOH 3<1<2

COOH COOH COOH COOH
NO2
(iii) < < < 3<4<2<1
OCH3 NO2 NO2

2. (a) What happens when (CBSE Term – II_2022)
(i) Propanone is treated with CH3MgBr and then hydrolysed ?
(ii) Ethanal is treated with excess ethanol and acid ?
(iii) Methanal undergoes Cannizzaro reaction ? [1×3 =3]
OR
(b) Write the main product in the following reactions :
(i) 2CH3COCl + (CH3)2Cd
Zn (Hg)/Conc.HCl
(ii) CH3CH2CHO
(iii) COONa + NaOH CaO [1×3=3]

CBSE 77
p
CH3 CH3
Ans. (a) (i) C = O + CH3MgBr C — OMgBr
CH3 CH3
CH3
H+ H2O
CH3
Br
CH3 – C – OH + Mg
CH3 OH
2-Methyl propan-2-ol
CH3 OC2H5
HCl
(ii) CH3–C–H + C2H5OH C
Excess H OC2H5
O
conc. NaOH
(iii) 2HCHO CH3OH + HCOONa
OR
(b) (i) CH3COCH3
Acetone
(ii) CH3CH2CH3
Propane
(iii)
Cyclohexane
3. (a) (i) Which acid of the following pair would your expect to be stronger ?
(CBSE Term – 2_2022)
F–CH2–COOH or CH3–COOH
(ii) Arrange the following compounds in increasing order of their boiling points :
CH3CH2OH, CH3–CHO, CH3–COOH
(iii) Given simple chemical test to distinguish between Benzaldehyde and
Acetophenone. [1×3=3]
OR
(b) (i) Which will undergo faster nucleophilic addition reaction ?
Acetaladehyde or Propanone
(ii) What is the composition of Fehling's reagent ?

(iii) Draw structure of the semicarbazone of Ethanal. [1×3=3]

78 Chemistry
Ans. (a) (i) F–CH2–COOH due to electron withdrawing effect of F.
(ii) CH3CHO < CH3CH2OH< CH3–COOH
(iii) Iodoform test :
COCH3 COONa
4NaOH + 3I2 + CHI3 + + 3NaI + 3H2O
Acetophenone will give iodoform test with yellow ppt.

CHO
+ 4NaOH + 3I2 No reaction
Benzaldehyde give tollen's test but acetophenone will not give tollen's test.
OR
(b) (i) Acetaldehyde, due to less steric hindrance.
(ii) Fehling solution A – aqueous solution of CuSO4.
Fehling solution B – Roschelle salt (sodium potassium tartarate + NaOH)
O
H3C H3C O
+ H2N – HN – C – NH2
C=O C = N – NH – C – NH2 + H2O
(iii) (Semicarbazide)
H H Acetaldehyde
Acetaldehyde Semicarbazone
4. (a) Draw the structures of the following derivatives : [1 × 2 = 2]

(i) 2, 4-DNP of benzaldehyde (CBSE Compartment_2021)
(ii) Propanone oxime
(b) Complete the following synthesis : [1]
CH2CH

KMnO4
(i) ?
KOH, heat
CH3COCl
(ii) ?
anhyd. AlCl3
(c) Carboxylic acid is a stronger acid than phenol. Justify. [1]

OR
(a) An organic compound ‘A’ with molecular formula C4H8O2 was hydrolysed with dil. H2SO4 to
give a carboxylic acid ‘B’ and an alcohol ‘C’. ‘C’ on dehydration gives ethene and ‘C’ also on
oxidation gives back ‘B’. Identify ‘A’, ‘B’ and ‘C’ and write the chemical equations for the
reactions involved. [3]
(b) How will you convert ethanal into the following compounds ? [1 × 2 = 2]
(i) Ethanol (ii) Ethane

CBSE 79
NO2
H3C
Ans. (a) (i) (ii) C = N – OH
C = N NH NO2 H3C
H
O
COOH C–CH3
(b) (i) (ii)
O O O O O
(c)
I II III IV V
Un equivalent resonating structures
–
O O
R—C – R—C
O O
I' II'
Equivalent resonating structures, more stable
The carboxylate ion is more stabilised than phenoxide ion, so carboxylic acids are more acidic
than phenols.
OR
O
A CH3–C–OC2H5
O
B CH3–C–OH
(a)
C C2H5OH
O O
H2O
CH3–C–OC2H5 CH3–C–OH + C2H5OH
C4H8O2 dil. H2SO4 (B) (C)
(A)
H 2SO 4
C2 H 5 OH 443K
CH 2 CH 2
(C) Ethene
O O
[O] [O]
C2H5–OH (H2SO4 + K2Cr2O7)
CH3–C–H CH3–C–OH
(C) (B)
O
(b) (i) LiAlH4
CH3 – C– H + 2H CH3 – CH2 – OH
Ethanal Ethanol
H
(ii) 4H
C=O CH3–CH3 + H2O
H3C Ethanal Zn– Hg, HCl Ethane

80 Chemistry
5. Iodoform test in not given by (CBSE 2020)
(A) Ethanol (B) Ethanal (C) Pentan-2-one (D) Pentan-3-one
Ans. (D)
6. What is the correct IUPAC name of the given compound ? (CBSE 2020)
(A) 2,2-Dimethylbutanoic acid
(B) 2-Carboxyl-2-methylbutane
(C) 2-Ethyl-2-methylpropanoic acid
(D) 3-Methylbutane carboxylic acid
Ans. (A)
(a) Propanone is treated with methylmagnesium bromide and then hydrolysed, and
(b) benzene is treated with CH3COCl in the presence of anhydrous AlCl3
Ans. (a) (CH3)3C-OH/tertiary butyl alcohol is formed.
(b) C6H5COCH3/acetophenone is formed
8. Write structures of main compounds A and B in each of the following reactions : (CBSE 2019)
PCl5 H2 /Pd BaSO4
(a) C6 H5COOH A B
(b) CH 3 CN
(i)CH3 MgBr
A
Zn(Hg)/ conc.HCl
B
(ii) H 3 O
Ans. (a) A = C6H5COCl B = C6H5CHO

(b) A = CH3COCH3 B = CH3CH2CH3
9. (a) Give reasons :

(i) Benzoic acid is a stronger acid than acetic acid. (CBSE 2019)
(ii) Methanal is more reactive towards nucleophilic addition reaction than ethanal.
(b) Give a simple chemical test to distinguish between propanal and propanone.
Ans. (a) (i) Due to the electron donating inducting effect (+I) by the alkyl group on acetic acid
destabilise the conjugate base of acetic acid.
(ii) Aldehyde which is a functional group (CHO) is more reactive due to less steric
effect.
(b) Propanal being an aldehyde reduces Fehling's solutions to a red-brown ppt of Cu2O, but
propanone being a keton does not. Propanone being a ketone does not.
Propanal being an aldehye reduces Tollen's reagent to a silver mirror but propanone being a
ketone does not.

CBSE 81
10. Write structures of main compounds A and B in each of the following reactions : (CBSE 2019)
PCC CH3OH/dryHCl(g) NaOI
(a) CH3 CH2 OH A B (b) C6 H 5 COCH3 A B
Ans. (a) A CH3CHO ; B CH3–CH–OH (b) C6 H 5 COCH 3 NaOI

CHI 3 C6 H 5 – COONa
OCH3
11. How do you convert the following ? (CBSE 2018)
(a) Ethanal to Propanone (b) Toluene to Benzoic acid
OR
Account for the following :
(a) Aromatic carboxylic acids do not undergo Friedel–Crafts reaction.
(b) pKa value of 4-nitrobenzoic acid is lower than that of benzoic acid.
Ans. (a) Ethanol to propanone :-
O O MgX
(Grignard reagent)
CH3 – C – H + CH3 – Mg X CH 3 – CH H O/H+ CH3 – CH – OH
2
CH3 CH3
(Ethanol) (Adduct)
CrO3
O
CH3 – C – CH3
Propanone
(b) Toluene to Benzoic Acid
CH3 COOK COOH
KMnO4
–KOH/ H3 O
+
Benzoic acid
OR
(a) In case of aromatic carboxylic acid –COOH attach to the benzene ring having electron
withdrawing effect and deactivated the benzene ring, hence do not exhibit Friede-Craft
reaction.
(b) pKa value of 4-nitrobenzoic acid is lower than benzoic acid is due to e– withdrawing nature
of —NO2 attach at para position of benzene due to which tendency to loose H+ ion increases
and acidic character increases.
12. (A), (B) and (C) are three non-cyclic functional isomers of a carbonyl compound with molecular
formula C4H8O. Isomers (A) and (C) give positive Tollens' test whereas isomer (B) does not give
Tollens' test but gives positive Iodoform test. Isomers (A) and (B) on reduction with
Zn(Hg)/conc. HCl give the same product (D). (CBSE 2018)
(a) Write the structures of (A), (B), (C) and (D).
(b) Out of (A), (B) and (C) isomers, which one is least reactive towards addition of HCN
O
Ans. (a) (A) CH3 – CH2 – CH2 – CHO (B) CH3 – C – CH2 – CH3
CH3 O
(C) CH3 – CH – C – H (D) CH3 – CH2 – CH2 – CH3
(b) B is ketone, so it will be less reactive towards nucleophilic addition reaction, with HCN
due to + I effect & steric hinderance
(Inductive)

82 Chemistry
1. Write the structure of 2-Hydroxybenzoic acid. [1]

2. Arrange the following in the increasing order of their reactivity towards nucleophilic addition
reaction:
CH3–CHO, C6H5COCH3, HCHO [1]
3. Write the product in the following reaction. [1]
1.(i Bu)2 AlH
CH3CH2CH=CH–CH2CN 2. H 2O
4. A and B are two functional isomers of compound C3H6O. On heating with NaOH and I2, isomer
A forms yellow precipitate of iodoform whereas isomer B does not form any precipitate. Write
the formulae of A and B. [2]
5. Account for the following : [2]
(a) Aromatic carboxylic acids do not undergo Friedel–Crafts reaction.
(b) pKa value of 4-nitrobenzoic acid is lower than that of benzoic acid.
6. Why pKa of Cl–CH2–COOH is lower than the pKa of CH3COOH ? [2]
7. Write the chemical equations to illustrate the following name reactions: [2]
(i) Rosenmund reduction (ii) Cannizzaro's reaction
8. (A), (B) and (C) are three non-cyclic functional isomers of a carbonyl compound with molecular
formula C4H8O. Isomers (A) and (C) give positive Tollens' test whereas isomer (B) does not give
Tollens' test but gives positive Iodoform test. Isomers (A) and (B) on reduction with
Zn(Hg)/conc. HCl give the same product (D).
(a) Write the structures of (A), (B), (C) and (D).
(b) Out of (A), (B) and (C) isomers, which one is least reactive towards addition of HCN ? [3]
9. How will you convert the following in not more than two steps : [3]
(i) Benzoic acid to Benzaldehyde

(ii) Acetophenone to Benzoic acid
(iii) Ethanoic acid to 2-Hydroxyethanoic acid
10 Write the structures of A, B, C and D in the following reactions : [3]
(i) SnCl2–HCl dil..NaOH heat
CH3CN A B C
(i) H2O
HCN
D
11. Write the product(s) in the following reactions : [5]
O COONa
CaO
(i) + HCN ? (ii) + NaOH ?
H 2 N –NHCONH 2
(iii) CH3 – CH = CH – CN (a ) DIBAL H
(b ) H 2 O
? (iv) CH3 – C =O ?
|
CH 3
(a)KMnO 4 /KOH
(v) C6 H5 CH 2 CH 3 (b)H
?

CBSE 83
MOCK TEST SOLUTIONS

COOH
OH
1.
2. C6H5COCH3 < CH3CHO < HCHO
3. CH3CH2CH = CH – CH2CHO
4. A : CH3COCH3,
B : CH3CH2CHO
5. (a) In case of aromatic carboxylic acid – COOH attach to the benzene ring having electron
withdrawing effect and deactivated the benzene ring, hence do not exhibit Friede-Craft reaction.
(b) pKa value of 4-nitrobenzoic acid is lower than benzoic acid is due to e¯ withdrawing nature
of – NO2 attach at para position of benzene due to which tendency to loose H+ ion increases
and acidic character increases.
6. Stronger–I effect of Cl, stronger acid less pka/strong electron withdrawing power of Cl.
COCl CHO
7. (i) H2
Pd–BaSO4
Benzaldehyde
NaOH
(ii) HCHO + HCHO CH3OH + HCOONa
Methanal Methanol
8. (a) (A) CH3 – CH2 – CH2 – CHO
O
||
(B) CH 3 C CH 2 CH 3
CH 3 O
| ||
(C) CH 3 CH C H
(D) CH3 – CH2 – CH2 – CH3
(b) B is ketone, so it will be less reactive towards nucleophilic addition reaction, with HCN due
to +I effect & steric hinderance (Inductive)

84 Chemistry
COOH COCl CHO
SOCl 2 Resonmund's
9. (i) reduction
Pd/BaSO 4
Benzoic Benzoyl Benzaldehyde
acid chloride
COCH3 COONa COOH
I 2 /NaOH H 3O +
(ii)
Acetophenone Sodium benzoate Benzoic

acid
CH3 KMnO COOK COOH

4
(iii) –KOH/ H3O

+
Benzoic acid
OH
|
10. A : CH3CHO B : CH3 CH CH 2 CHO
OH
|
C : CH3 – CH = CH – CHO D : CH3 CH CN
OH
CN
11. (i) (ii)
(iii) CH3 – CH = CH – CHO (iv) CH 3 C N NH CO NH 2

|
CH3
(v) C6H5–COOH

CBSE 85
AMINE : (CHAPTER-13)
CHAPTER AT A GLANCE
Amine : Alkyl derivatives of NH3 is known as amine.
H
|
–H –H –H
H–N R – NH2 R 2 – NH R3 – N
| +(–R) +(–R) +(–R)
H
Ammonia Primary amine Sec. amine Ter. amine
functional group functional group functional group
– NH2 NH
N
Aliphatic amine : R – NH2, R2NH, R3N

NH2
Aromatic amine : Aniline
NAMING
Amine Common name IUPAC name
CH3–CH2–NH2 Ethylamine Ethanamine
CH3–CH2–CH2–NH2 n-Propylamine Propane-1-amine
CH3–CH–CH3 Isopropylamine Propane-2-amine

NH2
CH3–N–CH 2–CH3 Ethylmethylamine Ethylmethylamine

H
CH3–N–CH 3 Trimethylamine N, N-Dimethylmethanamine

CH3
node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\13_Amine
1 2 3 4
C2H5–N–CH2–CH2–CH2–CH3 N, N-Diethylbutylamine N, N–Diethylbutane-1-amine
C2H5
NH 2
1 2
CH 2 CH CH 2
3
Allylamine Prop-2-en-1-amine
NH2–(CH2)6–NH2 Hexamethylenediamine Hexane-1, 6-diamine
NH2 Aniline Aniline or Benzenamine

86 Chemistry
NH2 o-Toluidine 2-Aminotoluene
CH3
NH2 p-Bromoaniline 4-Bromobenzenamine
or 4-Bromaniline
Br
N(CH3)2 N, N-Dimethylaniline N, N-Dimethylbenzenamine
GENERAL METHOD OF PREPARATION OF ALIPHATIC AND AROMATIC AMINE

1. Reduction of nitro compounds
2. Ammonolysis of alkyl halides
3. Reduction of nitriles
4. Reduction of amides
5. Gabriel phthalimide synthesis
6. Hoffmann bromamide degradation reaction
CHEMICAL REACTION OF AMINE

1. Basic character of amines
2. Alkylation
3. Acylation
4. Carbylamine reaction
ELECTROPHILIC SUBSTITUTION REACTION OF ANILINE

1. Halogenation (Bromination)
(a) Bromination : By bromine water
(b) Bromination of aniline by protection of –NH2 group.
2. Nitration
(a) Nitration of aniline by protection of –NH2 group :
(b) Direct nitration

3. Sulphonation

CBSE 87
PART-II
TOPIC : DIAZONIUM SALTS
The organic compound which have general formula is RN 2X known as Diazonium salt.
R Aryl group.
X Cl¯, Br¯, HSO4¯, BF4¯
N2Cl
Benzene diazoniumn chloride
N2Br
Benzene diazonium bromide
N2HSO4
Benzene diazonium hydrogen sulphate
N2BF4
Benzene diazonium tetrafluoroborate
Q. Draw the resonating structure of arene diazonium ion.

N N N=N N=N N=N N N
Ans.
GENERAL METHOD OF PREPARATION OF DIAZONIUM SALT
273 278K
C6H5NH2 + NaNO2 + 2HCl C6H5 + NaCl + 2H2O

88 Chemistry
PHYSICAL PROPERTIES
(1) Benzenediazonium chloride is a colourless crystalline solid.
(2) It is readily soluble in water and is stable in cold but reacts with water when warmed.
(3) It decomposes easily in the dry state.
(4) Benzenediazonium fluoroborate is water insoluble and stable at room temperature.
CHEMICAL REACTION OF DIAZONIUM SALTS
NAME REACTION
1. Sandmeyer Reaction
2. Gatterman Reaction
3. Balz-Schiemann Reaction
4. Gabriel phthalimide synthesis
5. Hoffmann bromamide degradation reaction
6. Carbylamine reaction
7. Hinsberg’s Test
8. Coupling Reactions

CBSE 89

1. How will you convert
(i) Benzene into aniline (ii) Benzene into N, N–dimethylaniline
(iii) Cl–(CH2)4–Cl into hexan-1, 6-diamine ?
NO2 NH2
HNO 3/ H 2SO 4 H 2/Pd
Ans. (i) (Nitration) Ethanol
Benzene Nitrobenzene Aniline
H CH3
NO2 NH2 N N
CH3 CH3
HNO3/ H 2SO 4 H 2/Pd CH3 Cl CH 3Cl
(ii) (Nitration) Ethanol
Benzene Aniline N, N–Dimethylaniline
Ethanolic NaCN H 2/Ni

(iii) Cl–(CH2) 4–Cl N C–(CH2)4–C N H2N–CH2–(CH2)4–CH2–NH2
1,4-Dichlorobutane Hexane-1, 6-diamine
2. Arrange the following in increasing order of their basic strength :

(i) C2H5NH2, C6H5NH2, C6H5CH2NH2 and (C2H5)2NH
(ii) C2H5NH2, (C2H5)2NH, (C2H5)3N, C6H5NH2
(iii) CH3NH2, (CH3)2NH, (CH3)3N, C6H5NH2, C6H5CH2NH2
Ans. (i) C6H5NH2 < C6H5CH2NH2 < C2H5NH2 < (C2H5)2NH
(ii) C6H5NH2 < C2H5NH2 < (C2H5)3 N < (C2H5)2 NH
(iii) C6H5NH2 < C6H5CH2NH2 < (CH3)3 N < CH3NH2 < (CH3)2NH
3. Complete the following acid-base reactions and name the products :
(i) CH3CH2CH2NH2 + HCl (ii) (C2H5)3N + HCl
+ – + –
Ans. (i) CH3CH2CH2NH2 + HCl CH3CH2CH2NH3Cl (ii) (C2H5)3N + HCl (C2H5)3 NHCl
n-Propylamine n-Propylammoniumchloride Triethylamine Triethylammoniumchloride
4. Write reactions of the final alkylation product of aniline with excess of methyl iodide in the
presence of sodium carbonate solution.
Ans. Aniline reacts with methyl iodide to produce N, N-dimethylaniline.
H CH3
NH2 N N
CH3 CH3
CH 3l CH3l
Aniline N-Methyl aniline N, N–Dimethylaniline
With excess methyl iodide, in the presence of Na2CO3 solution, N, N-dimethylaniline produces
N, N, N-trimethylanilinium carbonate.
CH3 + +
N N(CH3)3I— N(CH3) 3
CH3
Na2CO3 CO32— + 2NaI
+ CH3I
2
N, N–Dimethylaniline N, N, N–Trimethylanilinium Iodide N, N, N–Trimethylanilinium Carbonate
5. Write chemical reaction of aniline with benozyl chloride and write the name of the product
obtained.
H
.. Base
Ans. N–H + C–Cl +
N – C – Cl HCl + N—C
H O H O H O
N-Phenylbenzamide
Aniline Benzoyl chloride

90 Chemistry
6. Write structures of different isomers corresponding to the molecular formula, C3H9N. Write
IUPAC names of the isomers which will liberate nitrogen gas on treatment with nitrous acid ?
Ans. The structures of different isomers corresponding to the molecular formula, C3H9N are given
below :
(a) CH3–CH2–CH2–NH2
Propan-1-amine (1°)
NH2
(b) CH3–CH–CH3
Propan-2-amine (1°)
(c) CH3–NH–C2H5
N-Methylethanamine (2°)
CH3
(d) CH3–N–CH3
N, N-Dimethylmethanamine (3°)
1° amines, i.e. (a) propan -1-amine, and (b) Propan - 2-amine will liberate nitrogen gas on
treatment with nitrous acid.'
CH3CH2CH 2NH2 + HNO2 CH3CH2CH2OH + N2 + HCl
Propan -1-amine Propan -1-ol
CH3–CH–CH3 + HNO2 CH3–CH2–CH2 +N2 + HCl

NH2 OH
Propan-2-amine Propan-2-ol
7. Convert
(i) 3-Methylaniline into 3-nitrotoluene. (ii) Aniline into 1, 3, 5-tribromobenzene
+ –
NH2 N2Cl
273-278 K
Ans. (i) + NaNO2 + 2HCl + NaCl + 2H2O
CH3 CH3
3-Methylaniline HBF 4
+ –
NO2 N2BF4
NaNO 2
NaBF4 + N2 + Cu,
CH3 CH3
3-Nitrotoluene
+ –
NH2 NH2 N2Cl
Br Br Br Br Br Br
(ii) Br2 /H2 O NaNO2/HCl H 2O
H 3PO 2
Aniline Br Br Br
1,3,5 - Tribromobenzene

CBSE 91
8. Write chemical equations for the following reactions :
(i) Reaction of ethanolic NH3 with C2H5Cl.
(ii) Ammonolysis of benzyl chloride and reaction of amine so formed with two moles of CH3Cl.
H
Ans. (i) C2H 5–Cl NH 3
C2H5–NH2 C H –Cl C2H5–N–C2H5 C H –Cl C2H5–N–C 2H 5
2 5 2 5 C2H5–Cl
(C 2H 5)3NCl
quaternary
C 2H 5 ammonium salt
Chlorethane Ethanamine N-Ethylethanamine N,N-Diethylethanamine

NH3 2CH3Cl
(ii) C 6H5–CH2–Cl C6H 5–CH 2NH2 C6H5–CH2–N–CH3
CH3
Benzylchloride Benzylamine N,N-Dimethylphenylmethanamine
9. Write chemical equations for the following conversions:
(i) CH3.CH2.Cl into CH3.CH2.CH2.NH2
(ii) C6H5.CH2.Cl into C6H5.CH2.CH2.NH2
Ethanolic NaCN Reduction
Ans. (i) CH3 CH2 Cl CH3 CH 2 C N CH 3 CH 2 CH 2 NH 2
Chlorethane Phenylethanenitrile Pr opan 1 a min e
(ii) C6H 5 CH 2 Cl Ethanolic NaCN

C6H 5 CH 2 C N H2 / Ni
C 6H 5 CH 2 CH 2 NH 2
Chlorophenylmethane Phenylethanenitrile 2 P henylethana min e
(Benzyl chloride) (Benzyl cyanide)
10. Write structures and IUPAC names of

(i) the amide which gives propanamine by Hoffmann bromamide reaction.
(ii) the amine produced by the Hoffmann degradation of benzamide.
Ans. (i) Propanamine contains three carbons. Hence, the amide molecule must contain four carbon atoms.
Structure and IUPAC name of the starting amide with four carbon atoms are given below :
CH3–CH2–CH 2–C–NH 2 (Butanamide)
O
(ii) Benzamide is an aromatic amide containing seven carbon atoms. Hence, the amine formed
from benzamide is aromatic primary amine containing six carbon atoms.
NH2
(Aniline or benzenamine)
11. Arrange the following in decreasing order of their basic strength : C6H5NH2, C2H5NH2, (C2H5)2NH, NH3
Ans. The decreasing order of basic strength of the above amines and ammonia follows the following
order :
(C2H5)2NH > C2H5NH2 > NH3 > C6H5NH2
12. How will you convert 4-nitrotoluene to 2-bromobenzoic acid ?

CH3 CH3 CH3 CH3
Br Br Br
Br2 Sn / HCl NaNO2 / HCl
Ans. 273-278 K
NO2 NO2 NH2 N2Cl

H2O H3PO2
COOH CH3
Br Br
KMnO 4
–
OH

92 Chemistry
1. Arrange the following in increasing order of their basic strength :
(i) C2H5NH2, C6H5NH2, C6H5CH2NH2 and (C2H5)2NH
(ii) C2H5NH2, (C2H5)2NH, (C2H5)3N, C6H5NH2
(iii) CH3NH2, (CH3)2NH, (CH3)3N, C6H5NH2, C6H5CH2NH2
Ans. (i) C6H5NH2 < C6H5CH2NH2 < C2H5NH2 < (C2H5)2NH
(ii) C6H5NH2 < C2H5NH2 < (C2H5)3 N < (C2H5)2 NH
(iii) C6H5NH2 < C6H5CH2NH2 < (CH3)3 N < CH3NH2 < (CH3)2NH
2. Arrange the following :

(i) In decreasing order of the pKb values :
C2H5NH2, C6H5NHCH3, (C2H5)2NH and C6H5NH2
(ii) In increasing order of basic strength :
C6H5NH2, C6H5N(CH3)2, (C2H5)2NH and CH3NH2
(iii) In increasing order of basic strength :
(a) Aniline, p-nitroaniline and p-toluidine
(b) C6H5NH2, C6H5NHCH3, C6H5CH2NH2
(iv) In decreasing order of basic strength in gas phase :
C2H5NH2, (C2H5)2NH, (C2H5)3N and NH3
(v) In increasing order of boiling point :
C2H5OH, (CH3)2NH, C2H5NH2
(vi) In increasing order of solubility in water :
C6H5NH2, (C2H5)2NH, C2H5NH2
Ans. (i) C6H5NH2 > C6H5NH–CH3 > C2H5NH2 > (C2H5)2NH

(ii) C6H5NH2 < C6H5N(CH3)2 < CH3NH2 < (C2H5)2 NH
(iii) (a) p – nitroaniline < aniline < p - toluidine
(b) C6H5 NH2 < C6H5NHCH3 < C6H5CH2NH2
(iv) (C2H5)3 N > (C2H5)2NH > C2H5NH2 > NH3
(v) (CH3)2 NH < C2H5NH2 < C2H5OH
(vi) C6H5NH2 < (C2H5)2 NH < C2H5NH2

CBSE 93
3. Complete the following reactions :
(i) C6H5NH2 + CHCl3 + alc. KOH
(ii) C6H5N2Cl + H3PO2 + H2O
(iii) C6H5NH2 + (conc.) H2SO4
(iv) C6H5N2Cl + C2H5OH
(v) C6H5NH2 + (aq.) Br2
(vi) C6H5NH2 + (CH3CO)2O
(vii) C6H5N2Cl ( i ) HBF4
( ii ) NaNO 2 / Cu,
Ans. (i) C6H5N = C

Phenyl isocyanide
(offensive smell)
(ii) C6H6 + N2 + H 3PO3+HCl

Benzene
+
(iii) C6H5NH3HSO4
—
Anilinium hydrogen
sulphate
Reduction
Cl + C H OH (iv) C6H6 + CH3CHO + N2 + HCl
Benzene Ethanal
NH2
Br Br
(v) + 3 HBr
Br
niline 2,4,6-Tribromoaniline
O
O
CH COOH
O (vi) C6H5–NH–C–CH3 + CH3COOH
O
Acetanilide
(vii)
NaNO /Cu
C6H5 NO2 + BF3 + NaF

Nitrobenzene
4. Write the preparation methods of Iso-cyanides :

Ans. (i) Carbylamine reaction :
R NH2 + CHCl3 + 3KOH (alc.) R –NC + 3KCl + 3H2O
Chloroform Carbylamine
C2H5Br + AgCN C2H5NC + AgBr
Ethyl carbil Amine

94 Chemistry
5. Give one chemical test to distinguish between the following pairs of compounds.
(i) Methylamine and dimethylamine (ii) Secondary and tertiary amines
(iii) Ethylamine and aniline (iv) Aniline and benzylamine
(v) Aniline and N - methylaniline
Ans. (i) Methylamine gives carbylamine reaction on heating with CHCl3 and alcoholic KOH. Gives
foul smelling (Carbyl amine).
Heat
CH3 NH2 + CHCl3 + 3KOH CH 3 NC + 3KCl + 3H2O
Carbylamine
where as Dimethylamine does not give this reaction.
(ii) Secondary amines given Hinsberg's test. Its gives insoluble substance with Hinsberg's
reagent (C6H5SO2Cl) which is not affected by base.
R 2 NH C 6 H 5 SO 2 Cl R 2 NSO 2 C 6 H 5 (N, N-Dialkyl benzene sulphonamide)
Sec. amine Benzene sulphonyl Insoluble inalkali
chloride
Where as tertiary amine does not react with Hinsberg's reagent.

(iii) Aniline gives azo dye test : Dissolve Aniline in conc. HCl and add ice - cold solution of
HNO2 (NaNO2 + dil HCl) at 273 K and then treat it with an alkaline solution of 2-napthol.
Appearance of brilliant orange or red dye indicates aromatic amine (ie Aniline).
Where as aliphatic amine (ie ethylamine) does not form dye. It will give brisk effervescence
due to the evolution of N2 but solution remain clear.
273 K + —
NH2 + con. HCl + HNO2 N NCl + 2H2O
Benzene diazonium
Chloride
OH OH
Dil NaOH
N+ NCl— + PH 9-10
N=N + HCl
2-Naphthol 1-Phenylazo-2-naphthol
(Orange dye)
(iv) Nitrous acid test : Benzylamine reacts with nitrous acid (HNO2) to form a diazonium salt
which being unstable even at low temperature, decomposes with evolution of N2 gas.
HNO 2 H2O
C6 H 5CH 2 NH 2 HCl
C6 H 5CH N NCl – C 6 H 5CH 2 OH N 2 HCl
Aniline reacts with HNO2 to form benzene diazonium chloride which is stable at 273-278 K
and hence does not decompose to evolve N2 gas.

+
NaNO 2HCl +
NH2 273 - 278 K
N NCl
–
Aniline Benzenediazonium chloride

(v) Carbylamine test : Aniline being a primary amine gives carbylamine test, i.e, when heated
with an alcoholic solution of KOH and CHCl3, it gives an offensive smell of phenyl
isocyanide. In contrast, N-methylaniline, being secondary amine does not give this test.
C6 H5 NH2 CHCl 3 3KOH C6 H5 NC
Aniline 1 a min e alc. Phenyl isocyanide
offensive smell
CHCl3 / KOH alc

C6 H5 NH CH 3 No reaction
N methylaniline 2 a min e

CBSE 95
6. Account for the following :
(i) pKb of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not.
(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
(iv) Although amino group is o- and p-directing in aromatic electrophilic substitution reactions,
aniline on nitration gives a substantial amount of m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction.
(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines.
(vii) Gabrial phthalimide synthesis is preferred for synthesising primary amines.
Ans. (i) In aniline, the lonepair of electrons on the N-atom are delocalized over the benzene ring.
Resulting, electron density on the nitrogen decreases. On the other hand, in CH3NH2, +I
effect of CH3 increases the electron density on the N-atom. Thus, aniline is a weaker base
than methylamine and hence its pKb value is higher than that of methylamine.
(ii) Ethylamine dissolves in water because it forms hydrogen bonds with water molecules. In
aniline due to large, hydro carbon part, the extent of H - bonding decreases considerably and
hence aniline is insoluble in water.
(iii) Methylamine being more basic than water, accepts a proton from water liberating OH ions.
.. +
CH3 NH2 + H – OH CH3 NH3 + OH—
These OH ions combine with Fe+3 ions present in H2O to form brown precipitate of hydrated
ferric oxide.
FeCl3 Fe+3 + 3Cl—
3
2Fe 6OH — 2Fe OH 3
or Fe2 O3 .3H2 O
Hydrated ferric oxide Brown ppt.
(iv) Nitration is usually carried out with a mixture of conc. HNO3 and conc. H2SO4. In presence
of these acids, most of aniline gets protonated to form anilinium ion. Thus in presence of
acids, the reaction mixture consists of aniline and anilinium ion. Now –NH2 groups in
aniline is o, p-directing and activating while the N H 3 group in anilinium ion in m-directing
and deactivating.
NH NH2 NH2 NH2
NO NO2
(HNO3 + + +
H SO )
Aniline 2% 47% NO2
NO2
51
+
NH2 NH3HSO4
+ H2SO4
Anilinium Hydrogen Sulphate
+
NH3
(Anilinium ion is meta directing)

96 Chemistry
(v) Aniline being a Lewis base, reacts with lewis acid AlCl3 to from a salt.
.. +
C 6 H 5 NH 2 + AlCl3 C 6 H 5 N H 2 AlCl3-
As a result, N of aniline acquires positive charge and hence it acts as a strong deactivating
group for electrophilic substitution reaction, consequently, aniline does not undergo Friedel
– Crafts reaction
(vi) The diazonium salts of aromatic amines are more stable than those of aliphatic amines due
to dispersal of the positive charge on the benzene ring as shown below.
+ + + + +
N.. N = N..
.. N = N.. N = N.. N..
..
..
N N
+ +
(vii) Gabriel phthalimide reaction gives pure primary amines without any contamination of secondary
and tertiary amines. Therefore, It is preferred for synthesising (aliphatic) primary amines.
7. How will you convert :
(i) Ethanoic acid into methanamine (ii) Hexanentirile into 1-aminopentane
(iii) Methanol to ethanoic acid (iv) Ethanamine into methanamine
(v) Ethanoic acid into propanoic acid (vi) Methanamine into ethanamine
(vii) Nitromethane into dimethylamine (viii) Propanoic acid into ethanoic acid
O O O
NH3 –+ –Br2+KOH
Ans. (i) CH3–C–OH CH3–C–ONH4 CH3–C–NH2 CH3NH2
–H2O
O
H2 O
(ii) CH3 ( CH2 )4 CN CH3 ( CH2 )4 C–NH2
O
Br2 + KOH
CH3 ( CH2 )4 NH2
PCl5 KCN alc H3 O

(iii) CH3 OH CH 3 Cl CH 3 CN
dil. HCl
CH 3 COOH
Methanol Ethanenitrile Ethanoic acid
O
(i) NH3
(iv) CH3 CH2 NH2 HNO2
CH3CH2 OH [O]
CH3COOH (ii) CH3C–NH2
Br2
KOH
CH3 NH2
(v) CH3 COOH LiAlH 4

Re duction
CH 3 CH2 OH P I2
CH3 CH2 I KCN
KI
CH 3 CH2 CN H2 O / H
CH 3 CH 2 COOH
Ethyliodide Ethylcyanide Pr opionic acid
(vi) CH3 NH2 HNO2

N 2 , H2 O
CH3 OH P I2
CH 3 I KCN
KI
CH3 CN Na / C2 H5 OH
Reduction
CH 3 CH 2 NH 2
Methyliodide Ethanamine
(vii) CH3 NO2 Sn / HCl

CH3NH 2 CHCl3 KOH
CH 3 NC Na C2 H5 OH
Reduction
CH 3NHCH 3
Dimethylamine
(viii) CH3 CH2 COOH NH3

CH 3CH2CONH 2 Br2 / KOH
CH 2CH 2NH 2
Propanoic acid Propanamide

CBSE 97
8. Describe a method for the identification of primary, secondary and tertiary amines. Also write
chemical euqations of the reactions involved.
Ans. Benzene sulphonyl chloride (C6H5SO2Cl), Which is also known as Hinsberg's reagent, reacts with
primary and secondary amine to form sulphonamides.
O O
S–Cl + H–N–C2H5 S–N–C2H5 + HCl
(i)
O H OH
N-Ethylbenzene sulphonamide
(soluble in alkali)
The hydrogen attached to nitrogen in sulphon amide is strongly acidic due to the presence of
strong electron with drawing sulphonyl group. Hence it is soluble in alkali.
O O
(ii) S–Cl + H–N–C2H5 S–N– C2H5 + HCl
O C2H5 O C2H5
N,N-Diethylbenzene sulphonamide
(insoluble in alkali because there is no
hydrogen atom attached to Nitrogen)
(iii) Tertiary amines do not react with benzene sulphonyl chloride.

This property of amines reacting with benzene sulphonylchloride in a different manner is used
for the distinction of primary, secondary and tertiary amines.
9. Accomplish the following conversions :
(i) Nirobenzene to benzoic acid (ii) Benzene to m-bromophenol
(iii) Benzoic acid to aniline (iv) Aniline to 2,4,6-tribromofluorobenzene
(v) Benzyl chloride to 2-phenylethanamine (vi) Chlorobenzene to p-chloroaniline
(vii) Aniline to p-bromoaniline (viii) Benzamide to toluene
(ix) Aniline to benzyl alcohol
+ —
NO2 NH2 N NCl CN COOH
Ans. (i) (i) Fe/HCl

(ii) NaOH
NaNO 2/HCl CuCN/KCN H 3O
Hydrolysis
273-278 K
dil HCl
Nitrobenzene Aniline Benzene diazonium Benzonitrile Benzoic acid
Chloride
NO2 NO2 NH2
Conc.HNO 3
+Conc.H2SO4 Br2/Fe Sn + HCl
(ii)
333 K
Br Br
Benzene Nitrobenzene m-Bromoaniline
m-Bromonitrobenzene
N2Cl OH
NaNO2/HCl H2O
Boiling
273-278 K dil H2SO 4
Br Br
m-Bromophenol
COOH COCl CONH2 NH2
PCl5 2NH 3 Br2 + KOH

(iii) -NH 4Cl
Benzoic acid Benzoyl Chloride Benzamide Aniline

98 Chemistry
+ –
NH2 NH2 N=NBF4 F
Br Br Br Br Br Br
Br2/H2O NaNO 2/HBF4 Heat
(iv) 273-278 K
Aniline
Br Br Br
2,4,6-Tribromonoaniline 2,4,6-Tribromo fluoro benzene
CH2Cl CH2CN CH2CH2NH2
(v) KCN (alc). Heat LiAlH 4

–KCl
Benzyl Chloride Phenyl ethanenitrile 2-Phenyl ethanamine
Cl Cl Cl
Conc. HNO3
+ Conc. H 2SO 4 Sn/HCl
(vi) Nitration (Reduction)
Chlorobenzene
NO2 NH2
P-Nitro chlorobenzene p-Chloro aniline
(Major product)
NH2 NHCOCH3 NHCOCH3 NH2
(CH3CO) 2O/CH 3COOH Br2/CH 3COOH H2O/OH —

(vii)
Aniline Acetanilide
Br Br
p-Bromo acetanilide p-Bromo aniline
(Major product)
+ —
CONH2 NH2 N2Cl
Br2/NaOH NaNO 2/HCl

(viii) Heat 273-278 K
Diazotisation
Benzamide Aniline Benzene diazonium
Chloride
CH3
H 3PO 2–H2O/Cu, Heat CH3Cl/Anhyd.AlCl3
Benzene
Toluene
+ —
NH2 N2Cl
NaNO 2/HCl H3PO2–H2O/Cu, Heat CH 3Cl/Anhyd. AlCl3

(ix) 273-278 K
Aniline Benzene diazonium Benzene

Chloride
CH3 CH2Cl CH2OH
Cl2(1 mole),hv KOH (aq.)

383 K (Hydrolysis)
Toluene Benzyl Chloride Benzylalcohol

CBSE 99
10. Give the structures of A, B and C in the following reactions :
NaCN OH – NaOH Br2
(i) CH3CH2I A Partial hydrolysis
B C
CuCN H2 O/H NH 3
(ii) C6H5N2Cl A B C
KCN LiAlH4 HNO2
(iii) CH3CH2Br A B 0 C
C
Fe /HCl NaNO2 HCl H2 O/H
(iv) C6H5NO2 A 273K
B C
NH 3 NaOBr NaNO2 /HCl
(v) CH3COOH A B C
Fe /HCl HNO2 C6 H5 OH
(vi) C6H5NO2 A 273K
B C
O O
NaOH + Br2
CH CH Ans.
I NaCN
(i) CHCH —C—NH
3CH 2CN
CH3—C—NH2 CH3–NH2
C H N Cl (ii)
C H NCClH COOH
C H CNC6H5CN
C H COONH
C 6H5COOH
Heat
C6H5CONH2
hydrolysis
Propanenitrile (A) Ethanamide (B) Methanamine (C) Cyanobenzene Benzoicacid (B) Benzamide (C)
(A)
HNO ,0C° + Fe/HCl +

KCN KCN LiAlH +
CH CH Br CH(iii)
CH CNCH[CH
3CHCH
2CNCH CH
N 3CH
NCl2CH
] 2NH2 (iv) C6H5NH2 C6H5N NCl
—
C6H5OH
Bromoethane Propanenitrile (A) Propan-1-amine (B) Propanol (C) Aniline (A) Benzenedizonium Phenol (C)
Chloride (B)
NaOBr Fe/HCl +
NaNO /HCl
(v)
NaOBr
CH3CONH2 CH3NH2 CH3O–CH3 (vi) C H NH6 5 2 C6H5N NCl— N=N OH
Ethanamide (A) Methanamine (B) Dimethyl ether(C)
Dimethyl ether Aniline (A) Benzenediazonium p-Hydroxyazo benzene (C)
Chloride (B)
11. An aromatic compound 'A' on treatment with aqueous ammonia and heating forms compound 'B'
which on heating with Br2 and KOH forms a compound 'C' of molecular formula C6H7N. Write
the structures and IUPAC names of compounds A, B and C.
Br2 + KOH
Ans. C6H5COOH
(i) (aq.) NH3
Heat
C6H5CONH2 C6H5NH2
Benzoic aicd (A) Benzamide (B) Aniline (C)
m.f. = C 7H 7NO mf = C6H7N
12. Complete the following reactions :

(i) C6H5NH2 + CHCl3 + alc. KOH (ii) C6H5N2Cl + H3PO2 + H2O
(iii) C6H5NH2 + H2SO4 (conc.) (iv) C6H5N2Cl + C2H5OH
(v) C6H5NH2 + Br2 (aq.) (vi) C6H5NH2 + (CH3CO)2O
(i ) HBF4
(vii) C6H5N2Cl (ii ) NaNO 2 / Cu,
+
Ans. (i) C6H5N = C (ii) C6H6 + N2 + H 3PO3+HCl (iii) C6H5NH3HSO4
—
Benzene Anilinium hydrogen

Phenyl isocyanide sulphate
(offensive smell)
NH2
O
Br O
Reduction Br
N Cl + C H OH (iv) C6H6 + CH3CHO + N2 + HCl (v)C H NH +
6 5 2 +O3 HBr
CH COOH (vi) C6H5–NH–C–CH3 + CH3COOH
Benzene Ethanal
Br O
Acetanilide
Aniline 2,4,6-Tribromoaniline
NaNO /Cu
(vii) C6H5 NO2 + BF3 + NaF
Nitrobenzene

100 Chemistry
13. Why aromatic primary amines can not be prepared by Gabriel phthalimide synthesis ?
Ans. The success of Gabriel phthalimide reaction depends upon the nucleophilic attack by the
phthalimide anion on the organic halogen compound.
O O
C C
N + R—X N—R
C C
O O
Phthalimide anion N-Alkylphthalimide
O
C
N + Ar—X × No reaction
Arylhalide
C
[Stable by resonance]
O
Phthalimide anion
As arylhalides do not undergo nucleophilic substitution reaction easily, aromatic primary amines
cannot be prepared by Gabriel phthalimide reaction.
14. Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid.
+
NH2 N NCl—
273-278 K
Ans. (i) + HNO2 + HCl + 2 H2O
Aniline Benzene diazonium

Chloride
+
(ii) CH3CH2NH2 +HNO2+ HCl 273-278 K
[CH3CH2–N N] Cl— H2O
CH3CH2OH+N2+HCl
Ethylamine Ethanediazonium Chloride Ethanol
(Unstable)
15. Give plausible explanation for each of the following :

(i) Why are amines less acidic than alcohols of comparable molecular masses ?
(ii) Why do primary amines have higher boiling point than tertiary amines ?
(iii) Why aliphatic amines are stronger bases than aromatic amines ?
Ans. (i) Loss of a proton from an amine gives amide ion (NH) while loss of a proton from alcohol
gives an alkoxide ion (OR) as shown below.

+
R-NH2 R-NH + H
Amine Amide ion
+
R-O-H R-O+H
Alcohol Alkoxide ion
As O is more electronegative than N, So negative charge on more electronegative atom is
more stable, As R O is more stable than RN H . Therefore amines are less acidic than
alcohols.

CBSE 101
(ii) Due to the presence of two H-atoms on N-atoms of 1° amines, they undergo extensive
intermolecular H-bonding while 3° amines due to the absence of H-atoms on N-atom there is
no hydrogen bonding takes place. So primary amines have higher b.p. than tertiary amines of
comparable molecular mass.
R R R
N—H N—H N—H
-----H -----H H
Inter molecular Hydrogen bonding in 1° amines.
R
|
R —N
|
R
No hydrogen bonding
(iii) Aliphatic amines are stronger bases than aromatic amines because :
(a) Due to resonance in aromatic amines, the lone pair of electrons on the nitrogen atom
gets delocalised over the benzene ring thus is less available for protonation.
(b) The aryl amine ions, have lower stability than the corresponding aliphatic amines i.e.,
protonation of aromatic amines is not favoured.
16. Give reasons for the followings :
(a) Acetylation of aniline reduces its activation effect.
(b) CH3NH2 is more basic than C6H5NH2
(c) Although –NH2 is o/p directing group, yet aniline on nitration gives a significant amount of
m-nitroaniline.
Ans. (i) Due to the resonance, the electron pair of nitrogen atom gets delocalised towards carbonyl
group/ resonating structures.
(ii) Because of +l effect in methylamine electron density at nitrogen increases whereas in
aniline resonance takes place and electron density on nitrogen decreases / resonating
structures.
(iii) Due to protonation of aniline/formation of anilinium ion
17. Write the IUPAC name of the given compound : CH3–NH–CH2–CH–CH3
CH3
Ans. N-methyl-2-methylpropanamine / 2-methyl-N-methylpropanamine
18. Write the structures of A, B and C in the following reactions:

– +
(i) C6H5— COO NH4 A Br2 /KOH B CH3 COCl / pyridine C
NaNO2 /Cu Sn/ HCl CHCl 3 alc.KOH
(ii) C6 H 5 N 2 BF4 A B C
Ans. (i) A : C6 H5 CONH2
B : C6 H5 NH2
C : C6 H5 NHCOCH3
(ii) A : C6 H5 NO2
B : C6 H5 NH2
C : C6H5 NC

102 Chemistry
19. An aromatic compound ‘A’ of molecular formula C7H7ON undergoes a series of reactions as
shown below. Write the structures of A,B, C, D and E in the following reactions:
Br2+KOH NaNO2+HCl CuCN
(C7H7ON) A C6H5NH2 B C
273 K
CHCl3+NaOH H2O
D E
+ –
CONH2 N NCl CN N C OH
Ans. A = B= C= D= E=
20. (a) Write the structures of the main products when aniline reacts with the following reagents :
(i) Br2 water (ii) HCl (iii) (CH3CO)2O/pyridine
(b) Arrange the following in the increase order of their boiling point :
C2H5NH2, C2H5OH, (CH3)3N
(c) Give a simple chemical test distinguish between the following pair of compounds (CH3)2 –
NH and (CH3)3N
NH2 +
NH3 Cl–
Br Br O
Ans. (a) (i) (ii) (iii) NH–C–CH3
Br
(b) (CH3)3N < C2H5NH2 < C2H5OH
(c) By Hinsberg test - Add Hinsberg reagent (Benzene sulphonyl chloride) in both compounds
(CH3)2–NH forms ppt insoluble in KOH while (CH3)3–N does not react node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\13_Amine
(or any other correct test)

CBSE 103
EXERCISE-3 RACE
Type 1 : Passage question 1 :
Amines are very reactive due to the difference in electronegativity between nitrogen and
hydrogen atoms and due to the presence of unshared pair of electrons over N-atom. The number
of hydrogen atoms attached to the N-atom decides the course of reactions of amine, that is why
amines differ in many reactions. In aromatic amines like aniline, electron density at ortho and
para-positions with respect to –NH2 group is high. Therefore, this group is ortho or para
directing and a powerful activating group.
(a) Amines on treatment with acids yield salt because they are :
(i) Basic in nature (ii) Acidic in nature
(iii) Amphoteric in nature (iv) None of these
(b) Amongst the following the strongest base in aqueous medium is .....
(i) CH3NH2 (ii) NCCH2NH2 (iii) (CH3)2NH (iv) C6H5NHCH3
(c) –NH2 group in the aniline is activating group and proceed reaction at :
(i) only para position (ii) only ortho position
(iii) meta position (iv) Both (i) and (ii)
(d) Which of the following group(s) increases basic strength of substituted aniline ?
(i) –OCH3 (ii) CH3 (iii) –SO3H (iv) Both (a) and (b)
Type 2 : Assertion and Reason :
Question 2 to 6 :- Note :- In the following questions a statement of assertion followed by a

reason. choose the correct answer out of the following choices –

104 Chemistry
2. Assertion : Hoffmann's bromide reaction is given by pri. amides
Reason : Primary amines are more basic than sec. amines
3. Assertion : Acylation of amines gives a monosubstituted product wheres alkylation of amines
gives polysubstituted product.
Reason : Acyl group sterically hinders the approach of further acyl groups.
4. Assertion : N-Ethylbenzenesulphonamide is soluble is alkali.
Reason : Hydrogen attached to nitrogen in sulphonamide is strongly acidic.
5. Assertion : Acetanilide is less basic than aniline.
Reason : Acetylation of aniline results in decrease of electron density on nitrogen.
6. Assertion : Aromatic 1° amines can be prepared by Gabriel Phthalimide Synthesis.
Reason : Aryl halides do not undergo nucleophilic substitution with anion formed by phthalimide.
Type 3 : Multiple choice question (one correct answer) (Questions 7 to 16) :
7. Propanamide on reaction with bromine in aqueous NaOH gives:
(i) Propanamine (ii) Ethanamine
(iii) N-Methyl ethanamine (iv) Propanenitrile
8. Which of the following synthetic method will result in a primary amine ?
(i) Gabriel's phthalimide synthesis (ii) Hoffmann bromide reaction
(iii) Reduction of nitrate (iv) All of these
9. Which of the following is a 3° amine ? node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\13_Amine
(i) 1-methylcyclohexylamine (ii) Triethylamine
(iii) tert-butylamine (iv) N-methylaniline
10. Indicate which nitrogen compound amongst the following would undergo Hoffmann reaction
(i.e. reaction with Br2 and strong KOH) to furnish the primary amine (R – NH2)
(i) RCONHCH3 (ii) RCOONH4
(iii) RCONH2 (iv) R – CONHOH

CBSE 105
11. Aniline reacts with concentrated HNO3 to give
NH2 NH2 NH2
NO2
(i) H2N NH2 (ii) , and
NO2
NO2
NO2
(iii) O O (iv)
12. Amongst the following, the strongest base in aqueous medium is _________.
(i) CH3NH2 (ii) NCCH2NH2 (iii) (CH3)2NH (iv) C6H5NHCH3
13. Ethylamine reacts with HNO2 to form _________.
(i) CH3 – O – N = O (ii) CH3 – O – CH3 (iii) C2H5OH (iv) CH3CHO
14. In the nitration of benzene using a mixture of conc. H2SO4 and conc. HNO3, the species which
initiates the reaction is ___________.
(i) NO2 (ii) NO+ (iii) NO2+ (iv) NO2¯
15. Reduction of aromatic nitro compounds using Fe and HCl gives __________.
(i) aromatic oxime (ii) aromatic hydrocarbon
(iii) aromatic primary amine (iv) aromatic amide
16. Acid anhydrides on reaction with primary amines give ____________.
(i) amide (ii) imide (iii) secondary amine (iv) imine

ANSWER KEY
Q. No. 1(a) (b) (c) (d) 2 3 4 5 6 7 8
Ans. (i) (iii) (iv) (iv) (iii) (iii) (iv) (ii) (iv) (ii) (i)
Q. No. 9 10 11 12 13 14 15 16
Ans. (ii) (iii) (ii) (iii) (iii) (iii) (iii) (i)

106 Chemistry

1. An Organic compound (A) with molecular formula C3H7NO on heating with Br2 and KOH forms
a compound (B). Compound (B) on heating with CHCl3 and alcoholic KOH produces a foul
smelling compound (C) and on reacting with C6H5SO2Cl forms a compound (D) which is soluble
in alkali. Write the structures of (A), (B), (C) and (D). [2]
(CBSE Term-II 2022)
Ans. CH3 – CH2 – CONH2+ Br2 + KOH CH3 – CH2 – NH2
(A) (B)
CHCl3+KOH
O CH3 – CH2 – N C
S–NH–CH2–CH3 (C)
O
(D)
2. Give reasons : (CBSE Term-II 2022)
(i) Ammonolysis of alkyl halides is not a good methods to prepare pure primary amines.
(ii) Aniline does not give Friedel-Crafts reaction.
(iii) Although –NH2 group is o/p directing in electrophilic substitution reactions, yet aniline on
nitration gives good yield of m-nitroaniline. [1×3=3]
Ans. (i) Ammonolysis of alkyl halides gives primary amine which behaves as a nucleophile and an
subsequent reaction with alkyl halide found 2°, 3° amines and finally forms quaternary
ammonium salt. which is difficult to separate.
(ii) Aniline does not undergo Friedel-Craft reaction due salt formation with aluminium
chloride, the Lewis acid, which is used as catalyst. Due to this, N-atom of aniline acquires
positive charge and hence, it acts as strong deactivating group for further reaction.
NH2 NH2 NH2 NH2
Conc.HNO3
NO2
(iii) Conc. H2SO4
+ +
NO2
Aniline NO2
(51%) (47%) (2%)
+
NH3
In strongly acidic medium aniline is protonated to form anilinium ion in which
– NH 3 group, + acts as meta directing.

+ +
:
C6 H5NH2 + H HSO4– C6H 5NH3 HSO4–

NH2 NH3HSO4
+ H2SO4
Lewis acid
Lewis base Anilinium hydrogen
Anilinium sulphate
(m-directing) (m–directing)

CBSE 107
3. In cold conditions, aniline is diazotized and then treated with N,N-dimethylaniline to give a
coloured product. The structure of the coloured product is : (CBSE Compartment_2021)
(A) (CH3)2–N NH
(B) CH3 N=N NH2
(C) OH N=N
(D) (CH3)2–N N=N
Ans. (D)
4. Describe a method for the identification of CH3NH2, (CH3)2NH and (CH3)3N. Also write the
chemical equations for the reactions involved. (CBSE Compartment_2021)
Ans. Hinsberg's Reagent (Benzene sulphonyl chloride) used for distinguish between primary amine,
sec. amine and ter. amine.
(i) Pri. amine react with benzene sulphonyl chloride to form N-alkyl benzene sulphonamide
which is soluble in base due to presence of active hydrogen.
O O
H H
S-Cl + N–CH3 –HCl
S-N
H CH3
O O
Methyl amine N–Methyl Benzene Sulphon amide
(Soluble in base)
(ii) Sec. amine react with Hinsberg reagent to form N, N–dialkyl benzene sulphonamide,
which insoluble in base.
O O
CH3 CH3
S–Cl + H–N S––N
CH3 –HCl CH3
O O
N,N-Dimethyl Benzene Sulphon amide)
(Insoluble in base)
(iii) Ter. amine do not react with Hinsberg reagent.

5. Out of the following, the strongest base in aqueous solution is (CBSE 2020) [1]
(A) methylamine (B) Dimethylamine (C) Trimethylamine (D) Aniline
Ans. (B)

108 Chemistry
6. Give the structures of A and B in the following sequence of reactions : (CBSE 2020)
NH3 NaOBr
(a) CH3COOH A B
Fe/HCl NaNO 2 HCl

(b) C6 H5 NO 2 A 0 5 C
B
H 2O / H
(c) C6 H 5 N 2 Cl CuCN
A B
OR
(a) How will you distinguish between the following pairs of compounds : [1 × 2 = 2]
(i) Aniline and Ethanmine
(ii) Aniline and N-methylaniline
(b) Arrange the following compounds in decreasing order of their boiling points : [1]
Butanol, Butanamine, Butane
Ans. (a) (A) CH3CONH2 (B) CH3NH2
(b) (A) C6H5NH2 (B) C6H5N2Cl
(c) (A) C6H5CN (B) C6H5COOH

OR
(a) (i) Add ice cold (NaNO2 + HCl) followed by phenol or -Naphthol to both the compounds.
Aniline forms orange red dye while ethylamine doen't
(ii) Add CHCl3 and KOH (alc.) to both the compounds.
Aniline gives four smelling isocyanides while N-Methylaniline doesn't
(b) Butanol > Butanmine > Butane
7. Arrange the following in decreasing order of basic character : [1]
C6H5NH2, (CH3)3N, C2H5NH2 (CBSE 2019)
Ans. (CH3)3N > C2H5NH2 > C6H5NH2

8. Complete the following reactions : [3]

CN
H2 / Ni
(a) (CBSE 2019)
CH3
Br H3PO2+H2O
(b)
+
N2Cl–
CH2–NH 2
(c) Ethanolic KOH
+ CHCl3

CBSE 109
OR
How do you convert the following : [3]
(a) N-phenylethanamide to p-bromoaniline
(b) Benzene diazonium chloride to nitrobenzene
(c) Benzoic acid to aniline
CH2NH 2 CH3
Br CH2NC
Ans. (a) (b) (c)
OR
O O
H–N–C–CH3 H–N–C–CH 3 NH2
– +
Br2 OH or H
(a) CH3 COOH
Br Br
+ –
N2+Cl
–
N2BF 4 NO2
NaNO 2
(b) +HBF4 Cu,
Fluoroboric
acid
COOH CONH2 NH2
NH3 Br 2/KOH
(c)
Heat
Benzoic acid Benzamide Aniline
9. Arrange the following in increasing order of pKb values : (CBSE 2019)
C6H5CH2NH2, C6H5NHCH3, C6H5NH2 [1]
Ans. C6H5CH2NH2 < C6H5NHCH3 < C6H5NH2

10. Arrange the following in decreasing order of solubility in water : [1]
(C2H5)2NH, C2H5NH2, C6H5NH2 (CBSE 2019)
Ans. (C2H5)2NH > C2H5NH2 > C6H5NH2

11. (a) Write the reactions involved in the following : (CBSE 2018)
(i) Hoffmann bromamide degradation reaction
(ii) Diazotisation
(iii) Gabriel phthalimide synthesis
(b) Give reasons :
(i) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
(ii) Aromatic diazonium salts are more stable than aliphatic diazonium salts.

110 Chemistry
OR
(a) Write the structures of the main products of the following reactions :
NH2
(CH3CO)2O (CH3)2NH
(i) (ii) SO2Cl
Pyridine
(iii)
(b) Give a simple chemical test to distinguish between Aniline and N, N-dimethylaniline.
(c) Arrange the following in the increasing order of their pKb values :
C6H5NH2, C2H5NH2, C6H5NHCH3
Ans. (a) (i) Hoffmann Bromamide degradation reaction :
O
R – C – NH2 + Br2 + 4NaOH R – NH2 + Na2CO3 + 2NaBr + 2H2O
(ii) Diazotisation
273–278 K + –
C6H5NH2 + NaNO2 + 2 HCl CC66H
H55N2Cl
NH 2 Cl
Aniline Aromatic diazonium
(iii) Gabriel phthalimide synthesis

O O
C C CO
Alc. KOH –+ –KBr
NH NK
N N–C 2H 5
C2H5Br/
C C CO
n-ethyl phthalimide
O O
(Potassium pthalimide)
H2O OH–/
COOH
C2H5 – NH2 +
COOH
ethanamine
(b) (i) Because of the combined factors of inductive effect and solvation or hydration effect.
(ii) The aromatic diazonium salt more stable than Aliphatic diazonium salt due to
resonance.
N N N=N N=N N=N

CBSE 111
OR
O
NH2 NH–C–CH3
O
(CH 3CO) 2 O
(a) (i) Pyridine
+ CH3–C–CH3
SO2Cl O
(CH3 )2 NH S N CH3
(ii)
O CH3
N, N–dimethyl benzenesulphonamide
N2 Cl
CH3CH 2OH
(iii) + N2 + HCl + CH3CHO
(b) Test to distinguish aniline & N, N-dimethyl aniline
(c) Increasing order
C 2 H5 NH 2 C6 H 5 NH CH 3 C6 H 5 NH 2

112 Chemistry

1. Write the IUPAC name of the given compound : CH3–NH–CH2–CH–CH3 [1]
CH3
2. S – Cl + H – N – C2H 5 ? [1]
O H
O
N–H CH3– C – Cl
3. H Base ? [1]
4. Give a simple chemical test to distinguish between Aniline and N, N-dimethylaniline. [2]
5. Although –NH2 is o/p directing group, yet aniline on nitration gives a significant amount of
m-nitroaniline. [2]
6. Write the reactions involved in the following : [2]
(i) Hofmann bromamide degradation reaction
(ii) Gabriel phthalimide synthesis
7. (a) Arrange the following in increasing order of pKb values : [2]
C6H5CH2NH2,C6H5NHCH3,C6H5NH2
(b) Arrange the following in decreasing order of solubility in water :
(C2H5)2NH, C2H5NH2, C6H5NH2
+
H2O/H NH3 Br2 + KOH
8. CH3CN A B C [3]
9. Write the structures of the main products when aniline reacts with the following reagents : [3]
(i) Br2 water (ii) HCl (iii) (CH3CO)2O/pyridine
10. Account for the following : [3]
(i) Primary amines (R-NH2) have higher boiling point than tertiary amines (R3N).
(ii) Aniline does not undergo Friedel – Crafts reaction.
(iii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
11. An aromatic compound ‘A’ of molecular formula C7H7ON undergoes a series of reactions as
shown below. Write the structures of A, B, C, D and E in the following reactions : [5]
Br2+KOH NaNO2+HCl CuCN
(C7H7ON) A C6H5NH2 B C
273 K
CHCl3+NaOH H2O
D E

CBSE 113
MOCK TEST SOLUTIONS

1. N-methyl-2-methylpropanamine / 2-methyl-N-methylpropanamine
O
2. S – N – C2H5
O H
N – C – CH3
3. H
4. Test to distinguish aniline & N, N-dimethyl aniline

O O
– HCl
S – Cl + H – NH S – NH
O O
Hinsberg Aniline Product
reagent
O N(CH3)2
S – Cl
+ No reaction
O
Benzene sulphonamide N, N–dimethyl aniline
5. Due to protonation of aniline/formation of anilinium ion.

6. (i) Hoffmann Bromamide degradation reaction :
(ii) Gabriel phthalimide synthesis

O O
C C CO
Alc. KOH – KBr
NH N C 2H 5
C2H5Br/
C C CO
e-ethyl pthalimide
O O
(Potassium pthalimide)
H2O OH¯ /
COOH
C2H5 – NH2 +
ethanamide COOH

114 Chemistry
7. (a) C6H5CH2NH2 < C6H5NHCH3 < C6H5NH2

(b) (C2H5)2NH > C2H5NH2 > C6H5NH2
O
||
8. (A) CH 3COOH (B) CH 3 C NH 2 (C) CH3 NH 2
Pr opanoic acid Ethanamide Methana mine
NH2 NH3+Cl¯
Br O
Br
9. (i) (ii) (iii) NH – C – CH3
Br
10. (i) Due to the presence of two H-atoms on N-atoms of 1° amines, they undergo extensive
intermolecular H-bonding while 3° amines due to the absence of H-atoms on N-atom there is
no hydrogen bonding takes place. So primary amines have higher b.p. than tertiary amines of
comparable molecular mass.
(ii) Aniline being a Lewis base, reacts with lewis acid AlCl3 to from a salt.
C 6 H 5 NH 2 AlCl 3 C 6 H 5 N H 2 AlCl 3 ¯
As a result, N of aniline acquires positive charge and hence it acts as a strong deactivating
group for electrophilic substitution reaction, consequently, aniline does not undergo
Friedel – Crafts reaction.
(iii)It is the combination of electron releasing nature of alkyl group, H-bonding and steric factors determine
the stability of ammonium cations formed in solution therefore Et 2 NH Et 3 N EtNH 2 is
order of Kb.
+
CONH2 N NCl¯ CN N C OH
11. A= B= C= D= E=

CBSE 115
BIOMOLECULES : (CHAPTER-14)
CHAPTER AT A GLANCE
Biomolecules : The organic compounds which are essential for growth and maintenance of life are
called biomolecules.
Eg : Carbohydrates, Proteins, Vitamins, Lipids, Enzymes, Harmones.
Carbohydrates : The optically active compounds which are either itself be or gives poly
hydroxy carbonyl compound on hydrolysis are called carbohydrates.
Classification :
(i) Monosaccharides : Those carbohydrates which cannot be hydrolysed into further simpler
carbohydrates E.g., glucose, fructose, galactose etc.
(ii) Disaccharides : Those carbohydrates which produces two monosaccharides on hydrolysis
E.g. sucrose, maltose and lactose.
(iii) Oligosaccharides : Those carbohydrates which give two to ten monosaccharides on
hydrolysis.
(iv) Polysaccharides : Those carbohydrates which on hydrolysis give large number of
monosaccharides hydrolysis E.g., starch, cellulose, glycogen.
Sugar : Carbohydrates which are sweet in taste.
(i) Reducing sugars : Those which reduce Fehling's or Tollen’s reagent due to availability of
free aldehydic groups Eg. glucose, fructose, galactose.

node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\14_Biomolecules
(ii) Non-reducing sugars : Those which do not reduce Fehling's or Tollen’s reagent they do not
have free aldehydic group. E.g., sucrose.
Glucose : It is a monosaccharide with molecular formula C6H12O6.
Preparation :
H
(i) From sucrose : C12 H 22 O11 H 2 O C6 H12 O6 C6 H12 O6
Glu cose Fru c tose
(ii) From starch :

H
(C6 H10 O5 )n nH2 O 393k; 2 3 atm
n C6 H12 O6
starch or Cellulose Glu cose

116 Chemistry
Structure :
Fischer structure :
(+) glucose has 'D' configuration as shown :

CHO
H–C–OH
HO–C–H
H–C–OH
H–C–OH
CH2OH
D-(+)-glucose
‘D’-means –OH group on first chiral ‘C’ from the bottom is on right hand and (+) means it is
dextrorotary i.e., it rotates plane polarized light towards right.
Glycosidic linkage : The linkage between two monosaccharide units through oxygen is called
the glycosidic linkage.
Proteins : These are macro molecules made up of amino acids joined by amide linkage is called
as peptide linkage. These are required for growth and development of the body.
Amino acids : These contain an amino (–NH2) and an acidic (–COOH) group and are therefore
amphoteric in nature. In solution they exist in the form of zwitter ion (a dipolar ion).
Essential and non-essential amino acids : The amino acids which are essential for health but
cannot be synthesis by the body are called essential amino acids. They are ten in number while
the remaining 10 which the human body can synthesis are called non-essential amino acids.
Zwitter ion : The dipolar structure of amino acids is called internal salt of Zwitter ion.
Classilication
Fibrous Protein Globular Protein
(i) Polypeptide chains run parallel or anti- (i) Chains of polypeptide coil around to
parallel and held together by hydrogen give a spherical shape.
and disulphide bonds
(ii) Generally insoluble in water e.g., (ii) Usually soluble in water, eg. insulin.
keratin.

CBSE 117
Structure and shape of protein
Primary structure Secondary structure Tertiary structure Quaternary structure
The specific sequence It is the shape in which Represents Protein can be
of amino acids in the the long polypeptide overall folding of composed of two or
polypeptide chain chain can exist It is of the polypeptide more polypeptide
Change in amino acids two types: -helix and chain. It gives rise chains called sub-
sequence changes the -pleated These to the fibrous or units. The spatial
protein completely. structures arise due to
globular molecular arrangement of
They have covalent regular folding of the
shapes. Forces these sub-units with
bonds. back bone of the
stabilizing the 2° respect to each
polypeptide chain due
and 3º structures other is quaternary
to H-bonding between
are hydrogen structure of the
the C=O and –NH–
groups of the peptide bonds, disulphide protein.
bond. linkages, van der

Waal's and
electrostatic
forces of
attraction
Native state of protein : The parental state or the natural state in which the protein is found.
Denaturation of protein : Destruction of the native state of protein is denaturation. It can he

brought by physical and chemical methods. The 2° and 3° structures are destroyed, only
1° structure is retained.
Vitamins : They are organic compounds required in the diet in small amounts to perform
specific biological functions for maintenance of optimum growth and health of the organism.
They are classified as follows :
(i) Fat soluble vitamins : Vitamin A, D, E and K. They are stored in liver and adipose (fat
storing) tissues.
(ii) Water soluble vitamins : B group vitamins and vitamin C, they need to supplied regularly in
diet as they are excreted in urine and cannot be stored (except vitamin B12) in our body.
Their deficiency causes diseases.

118 Chemistry
Nucleic acids : These are biomolecules which are long chain polymers of nucleotides. They are
of two types.
(i) Deoxyribonucleic acid (DNA)
(ii) Ribonucleic acid (RNA)
Nucleoside = Base + Sugar
Nucleotide = Base + Sugar + Phosphate
DNA RNA
(i) Double helical (i) Single stranded
(ii) Sugar is 2-deoxyribose (ii) Sugar is ribose
(iii) Bases A.T.G.C (iii)Bases A. U, G.C
(iv) Property of replication (iv) Do not replicate
(v) It is responsible for transmission (v) Helps in protein biosynthesis
of heredity character
Hormones :
Hormones are molecules that act as intercellular messengers. These are produced by endocrine
glands in the body and are poured directly in the blood stream which transports them to the site
of action.
In terms of chemical nature, some of these are steroids, e.g., estrogens and androgens; some are
poly peptides for example insulin and endorphins and some others are amino acid derivatives
such as epinephrine and norepinephrine.
(a) Insulin in keeping the blood glucose level within the narrow limit. Hormone glucagon tends
to increase the glucose level in the blood. The two hormones together regulate the glucose
level in the blood.
(b) Epinephrine and norepinephrine mediate responses to external stimuli. Growth hormones
and sex hormones play role in growth and development. Thyroxine produced in the thyroid
gland is an iodinated derivative of amino acid tyrosine. node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\14_Biomolecules
(c) Steroid hormones are produced by adrenal cortex and gonads (testes in males and ovaries in
females).
(d) Glucocorticoids control the carbohydrate metabolism, modulate inflammatory reactions and
are involved in reactions to stress.
(e) Testosterone is the major sex hormone produced in males. It is responsible for development
of secondary male characteristics (deep voice, facial hair. general physical constitution) and
estradiol is the main female sex hormon. It’s responsible for development of secondary
female charateristics and participates in the control of menstrual cycle.
(f) Progesterone is responsible for preparing the uterus for implantation of fertilised egg.

CBSE 119
1. Glucose or succrose are soluble in water but cyclohexane or benzene (simple six membered ring
compounds) are insoluble in water. Explain.
Ans. A glucose molecules contains five –OH groups while a sucrose molecule contains eight –OH
groups. Thus, glucose and sucrose undergo extensive H-bonding with water.
Hence, these are soluble in water.
But, cyclohexane and benezene do not contain –OH groups. Hence, they cannot undergo
H-bonding with water and as a result, they are insoluble in water.
2. What are the expected products of hydrolysis of lactose ?
Ans. On hydrolysis, it gives -D galactose and -D glucose.
3. How do you explain the absence of aldehyde group in the pentaacetate of D-glucose ?
Ans. D-glucose reacts with hydroxylamine (NH2OH) to form an oxime because of the presence of
aldehydic (–CHO) group of carbonyl carbon. This happens as the cyclic structure of glucose
forms an open chain structure in an aqueous medium, which then reacts with NH2OH to give an oxime.
CHO CH=N–OH
NH2OH
(CHOH)4 (CHOH)4
CH2OH CH2OH
Glucose Oxime
But pentaacetate of D-glucose does not react with NH2OH. This is because pentaacetate does not
form an open chain structure.
4. The melting points and solubility in water of amino acids are generally higher than that of the
corresponding halo acids. Explain.
Ans. Both acidic (carboxyl) as well as basic (amino) groups are present in the same molecule of amino
acids. In aqueous solutions, the carboxyl group can lose a proton and the amino group can accept,
thus giving rise to a dipolar ion known as a zwitter ion.

O O
R—CH—C—O—H R—CH—C—O—
+
NH2 NH3
(Zwitter ion)
Due to this dipolar behaviour, they have strong electrostatic interactions within them and with
water, But halo-acids do not exhibit such dipolar behaviour.
For this reason, the melting points and the solubility of amino acids in water is higher than those
of the corresponding halo-acids.

120 Chemistry
5. Where does the water present in the egg go after boiling the egg ?
Ans. When an egg is boiled, the proteins present inside the egg get denatured and coagulate. After
boiling the egg, the water present in it is absorbed by the coagulated protein through H-bonding.
6. Why cannot vitamin C be stored in our body ?
Ans. Vitamin C cannot be stored in our body because it is water soluble. As a result, it is readily
excreted in the urine.
7. What products would be formed when a nucleotide from DNA containing thymine is hydrolysed ?
Ans. When a nucleotide from the DNA containing thymine is hydrolyzed, thymine, -D-2-
deoxyribose and phosphoric acid are obtained as products.
8. When RNA is hydrolysed, there is not relationship among the quantities of different bases
obtained. What does this fact suggest about the structure of RNA ?
Ans. A DNA molecule is double-stranded in which the pairing of bases occurs. Adenine always pairs
with thymine, while cytosine always pairs with guanine. Therefore, on hydrolysis of DNA, the
quantity of adenine produced is equal of that off thymine and similarly, the quantity of cytosine
is equal to that of guanine.
But when RNA is hydrolyzed, there is no relationship among the quantities of the different bases
obtained. Hence, RNA is single-stranded.

CBSE 121
1. What are monosaccharides ?
Ans. Monosaccharides are carbohydrates that cannot be hydrolysed further to give simpler units of
polyhydroxy aldehyde or ketone.
2. What are reducing sugars ?
Ans. Reducing sugars are carbohydrates that reduce Fehling's solution and Tollen's reagent. All
monosaccharides and disaccharides, excluding sucrose, are reducing sugars.
3. Write two main functions of carbohydrates in plants.
Ans. Two main functions of carbohydrates in plants are :
(i) Polysaccharides such as strach serve as storage molecule.
(ii) Cellulose, a polysaccharide, is used to build the cell wall.
4. Classify the following into monosaccharides and disaccharides.
Ribose, 2-deoxyribose, maltose, galactose, fructose and lactose
Ans. Monosaccharides :
Ribose, 2-deoxyribose, galactose, fructose
Disaccharides :
Maltose, lactose
5. What do you understand by the term glycosidic linkage ?
Ans. Glycosidic linkage refers to the linkage formed between two monosaccharide units through an
oxygen atom by the loss of a water molecule.
For example, in a sucrose molecule, two monosaccharide units, - glucose and - fructose, are
joined together by a glycosidic linkage.
6
CH2OH
5 O 1
O
H H H HOH2C H
4 1 2 5
OH OH H O
3 2 H OH CH
6
2 OH
Glycosidic 3 4
H linkage
OH OH H
- D - glucose - D - fructose
Surcose
6. What is glycogen ? How is it different from starch ?
Ans. Glycogen is a carbohydrate (polysaccharide). In animals, carbohydrates are stored as glycogen.
Strach is a carbohydrate consisting of two components – amylose (15-20%) and amylopectin (80-85%).
However, glycogen consists of only one component whose structure is similar to amylopectin.
Also, glycogen is more branched than amylopectin.
7. What are the hydrolysis products of (i) sucrose and (ii) lactose ?
Ans. (i) On hydrolysis, sucrose gives one molecule of -D glucose and one molecule of -D-fructose.
(ii) The hydrolysis of lactose give -D-galactose and -D-glucose.

122 Chemistry
8. What is the basic structural difference between starch and cellulose ?

Ans. Starch consists of two components - amylose and amylopectin. Amylose is a long linear
chain of -D–(+)–glucose units joined by Cl – C4 glycosidic linkage ( -link).
Amylopectin is a branched-chain polymer of –D–glucose units, in which the chain is
formed by C1– C4 glycosidic linkage and the branching occurs by C1– C6 glycosidic linkage.
On the other hand, cellulose is a straight-chain polysacchoride of -D-glucose units joined
by C1– C4 glycosidic linkage ( -link).
9. What happens when D-glucose is treated with the following reagents ?
(i) HI (ii) Bromine water (iii) HNO3
Ans. (i) When D-glucose is heated with HI for a long time, n-hexane is formed.
CHO
Hl CH3–CH2–CH2–CH2–CH2–CH3
(CHOH)4
n - hexane
CH2OH
D - glucose
(ii) When D-glucose is treated with Br2 water, D-gluconic acid is produced.
CHO COOH
Br2water
(CHOH)4 (CHOH)4
CH2OH CH2OH
D - glucose D-gluconic acid
(iii) On being treated with HNO3, D-glucose get oxidised to give saccharic acid.
CHO COOH
HNO3
(CHOH)4 (CHOH)4
CH2OH COOH
D - glucose Saccharic acid
10. Eunmerate the reactions of D-glucose which cannot be explained by its open chain structure.
Ans. (1) Aldehydes give 2, 4-DNP test. Schiff's test, and react with NaHSO4 to form the hydrogen node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\14_Biomolecules
sulphite addition product. However, glucose does not undergo these reactions.
(2) The pentaacetate of glucose does not react with hydroxylamine. This indicates that a
free –CHO group is absent from glucose.
11. What are essential and non-essential amino acids ? Give two examples of each type.
Ans. Essential amino acids are required by the human body, but they cannot be synthesised in the
body. They must be taken through food. For example : valine and leucine
Non-essential amino acids are also required by the human body, but they can be synthesised in
the body. For example: glycine, and alanine
(i) Peptide linkage (ii) Primary structure (iii) Denaturation
12. Define the following as related to proteins
(i) Peptide linkage (ii) Primary structure (iii) Denaturation

CBSE 123
Ans. (i) Peptide linkage :
The amide formed between –COOH group of one molecule of an amino acid and –NH2 group of
another molecule of the amino acid by the elimination of a water molecule is called a peptide
linkage.
Peptide
linkage
–H2O
H2N—CH—COOH + H2N—CH—COOH H2N—CH—CO—NH—CH—COOH
CH(CH3)2 CH3 CH(CH3) 2 CH3
Valine Alanine Valylalanine (Val-Ala)
(ii) Primary structure :

The primary structure of protein refres to the specific sequence in which various amino acids are
present in it, i.e., the sequence of linkage between amino acids in a polypeptide chain. The
sequence in which amino acids are arranged is different in each protein. A change in the
sequence creates a different protein.
(iii) Denaturation :
When a protein in it's native form, is subjected to physical change, like change in temperature or
chemical change like change in pH, the hydrogen bonds are disturbed. Due to this, globules
unfold and helix get uncoiled and protein loses its biological activity. This is called denaturation
of protein.
13. What are the common types of secondary structure of proteins ?
Ans. There are two common types of secondary structure of proteins :
(i) - helix structure (ii) -pleated sheet structure
(i) - Helix structure
In this structure, the –NH group of an amino acid residue forms H-bonds with the group of
the adjacent turn of the right-handed screw ( -helix).
C
O
C
C
O
HO H
CN
N
O H
C
HCN
O
O H
N NH
H N
N
- helix structure

124 Chemistry
(ii) -pleated sheet structure

This structure is called so because it looks like the pleated folds of drapery. In this
structure, all the peptide chains are stretched out to nearly the maximum extension and then
laid side by side. These peptide chains are held together by intermolecular hydrogen bond
N
RCH N
N
H C=O RCH
N H RCH
C=O
RCH N H C=O
C=O RCH N
N RCH
H O=C
RCH N H O=C
H C=O RCH
N H
N H C=O
RCH
RCH N H
C RCH N C=O
C= RCH
=C
- pleated sheet structure
14. What type of bonding helps in stabilising the -helix structure of proteins ?
Ans. The H-bonds formed between the –NH group of each amino acid residue and the C=O group of
the adjacent turns of the -helix help in stabilising the helix.

15. How do you explain the amphoteric behaviour of amino acids ?
Ans. In aqueous solution, the carboxyl group of an amino acid can lose a proton and the amino group
can accept a proton to gives a dipolar ion known as zwitter ion. node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\14_Biomolecules
O O
R—CH—C—O—H R—CH—C—O—
+
NH2 NH3
(Zwitter ion)
Therefore, in zwitter ionic form, the amino acid can act both as an acid and as a base.
O O O
+ +
H H
R—CH—C—O— R—CH—C—O— R—CH—C—OH
OH +
OH +
NH2 NH3 NH3
Thus, amino acids show amphoteric behaviour.

CBSE 125
16. What are enzymes ?
Ans. Enzymes are proteins that catalyse biological reactions. They are very specific in nature and
catalyse only a particular reaction for a particular substrate. Enzymes are usually named after the
particular substrate or class of substrate and some times after the particular reaction.
For example, enzymes used to catalyse the hydrolysis of maltose into glucose is named as
maltase.
Again, the enzymes used to catalyse the oxidation of one substrate with the simultaneous
reduction of another substrate are named as oxidoreductase enzymes.
The name of an enzymes ends with '–ase'.
17. How are vitamins classified ? Name the vitamin responsible for the coagulation of blood.
Ans. On the basis of their solubility in water or fat, vitamins are classified into two groups.
(i) Fat-soluble vitamins : Vitamins that are soluble in fat and oils, but not in 'water, belong to
this group. For example: Vitamins A, D, E, and K
(ii) Water-soluble vitamins : Vitamins that are soluble in water belong to this group. For
example : B group vitamins (B1, B2, B6, B12, etc.) and vitamin C
However, biotin or vitamin H is neither soluble in water nor in fat.
Vitamin K is responsible for the coagulation of blood.
18. Why are vitamin A and vitamin C essential to us ? Give their important sources.
Ans. The deficiency of vitamin A leads to xerophthalmia (hardening of the cornea of the eye) and
night blindness. The deficiency of vitamin C leads to scurvy (bleeding gums).
The sources of vitamin A are fish liver oil, carrots, butter, and milk. The sources of vitamin C are
citrus fruits, amla, and green leafy vegatables.

19. What is the difference between a nucleoside and a nucleotide ?
Ans. A nucleoside is formed by the attachment of a base to l' position of sugar.
Nucleoside = Sugar + Base
5' O
HOH2C Base
4' 1'
HH HH
3' 2'
OH OH
Structure of a nucleoside

126 Chemistry
On the other hand, all the three basic components of nucleic acids (i.e., pentose sugar, phosphoric
acid, and base) are present in a nucleotide.
Nucleotide = Sugar + Base + Phosphoric acid
O
5' O
O——P—O—H2C Base
O — 4' 1'
HH HH
3' 2'
OH OH
Structure of a nucleotide
20. The two strands in DNA are not identical but are complementary. Explain.
Ans. In the helical structure of DNA, the two strands are held together by hydrogen bonds between
specific pairs of bases. Cytosin forms hydrogen bond with guanine, while adenine forms
hydrogen bonds with thymine. As a result, the two strands are complementary to each other.
21. Write the important structural and functional differences between DNA and RNA.
Ans. The structural differences between DNA and RNA are as follows :
DNA RNA
1. The sugar moiety in DNA The sugar moiety in RNA molecules is -D
molecules is -D-2 deoxyribose. ribose.
2. DNA contains thyamine (T). It does RNA contains uracil (U). It does not contain
not contain Uracil (U). thymine (T).
3. The helical structure of DNA is The helical structure of RNA is single-stranded.
double-stranded.
The functional differencess between DNA and RNA are as follows :

DNA RNA
1. DNA is the chemical basis of RNA is not responsible for heredity.
hereidity.
2. DNA molecules do not synthesise Proteins are synthesised by RNA molecules in the
proteins, but transfer coded message cells.
for the synthesis of proteins in the
cells.

CBSE 127
22. What are the different types of RNA found in the cell ?
Ans. (i) Messenger RNA (m-RNA)
(ii) Ribosomal RNA (r-RNA)
(iii) Transfer RNA (t-RNA)
23. (a) Which polysaccharide component of carbohydrates is commonly present in bread ?
(b) Write the two types of secondary structures of proteins ?
(c) Give two examples of water soluble vitamins ?
Ans. (a) Starch
(b) -Helix and -pleated sheets
(c) Vitamin B/B1/B2/B6/C (any two)
24. (i) Write one reaction of D-Glucose which cannot be explained by its open chain structure.
(ii) What type of linkage is present in Nucleic acids ?
(iii) Give one example each for water-soluble vitamins and fat-soluble vitamins?
Ans. (i) Sodium Hydrogen Sulphite reaction/Pentaacetate of glucose does not react with
Hydroxylamine/Schiff’s test (any one)
(ii) Phosphodiester linkage
(iii) Fat soluble - Vitamin A/D /E/ K
Water soluble - Vitamin B /C
25. (i) Which one of the following is a disaccharide : Starch, maltose, fructose, glucose
(ii) What is the difference between acidic amino acid and basic amino acid ?
(iii) Write the name of the linkage joining two nucleotides.
Ans. (i) Maltose
(ii) In acidic amino acid more carboxyl groups as compared to amino groups are present & In
basic amino acid more number of amino than carboxyl groups are present
(iii) Phosphodiester linkage.

128 Chemistry
EXERCISE-3 RACE
Type 1 : Passage question 1 :-
Glucose in an aldohexose. It can occur freely as well as in combined from in the nature.
It is present in sweet fruits and honey. It is also present in quantities in ripe grapes. As glucose is
an aldohexose, it consist of six C-atoms and an aldehyde group. It is the most abundant organic
compound on the earth and used as an immediate source fo energy for all metabolic reactions in
the animals.
(a) Which of the following statements is not true about glucose ?
(i) It is an aldohexose.
(ii) On heating with HI it forms n-hexane.
(iii) It is present in furanose form.
(iv) It does not give 2,4-DNP test.
(b) Which of the following reactions of glucose can be explained only by its cyclic structure?
(i) Glucose forms pentaacetate.
(ii) Glucose reacts with hydroxylamine to form an oxime.
(iii) Pentaacetate of glucose does not react with hydroxylamine.
(iv) Glucose is oxidised by nitric acid to gluconic acid.
(c) When glucose is treated with Br2 / water-
(i) Gluconic acid (ii) Saccharic acid (iii) acetic acid (iv) None of these
(d) The another name given to glucose is
(i) aldoheptose (ii) ketohexose (iii) pentose (iv) dextrose
Question 2 to 6 :- Note:- In the following questions a statement of assertion followed by a reason .
(iv) Assertion (A) is incorrect, but Reason (R) is correct statement. node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\14_Biomolecules
2. Assertion : Glycine must be taken through diet.

Reason : It is an essential amino acid.
3. Assertion : D (+) – Glucose is dextrorotatory in nature.
Reason : ‘D’ represents its dextrorotatory nature
4. Assertion : All naturally occurring -aminoacids except glycine are optically active.
Reason : Most naturally occurring amino acids have L-configuration.
5. Assertion : The two strands in double strand helix structure of DNA are complementary to each other.
Reason : Disulphide bonds are formed between specific pairs of bases.
6. Assertion : Glucose reacts with hydroxylamine to form an oxime and also adds a molecule of
hydrogen cyanide to give cyanohydrin.
Reason : The carbonyl group is present in the open chain structure of glucose.

CBSE 129
Type 3 : Multiple choice questions (one correct answer) (Questions 7 to 16):-
7. Curding of milk is an example of
(i) breaking of peptido linkage (ii) hydrolysis of lactose
(iii) breaking of protien into amina acids (iv) denaturation of protein
8. Proteins are found to have two different types of secondary structures viz. -halix and -Pleated
sheet structure, -helix structure of protein is stablized by:
(i) Peptide bonds (ii) Vander Walles forces
(iii) Hydrogen bonds (iv) Dipole-dipole interactions
9. Nucleic acids are the Polymers of:
(i) Nucleosides (ii) Nucleotides (iii) Bases (iv) Sugars
10. Each Polypeptide in protein has amino acids linked with each other in a specific sequence. This
sequence of amino acids is said to be_________:
(i) Primary structure of proteins
(ii) Secondary structure of proteins
(iii) tertiary structure of proteins
(iv) Quaternary structure of propetins
11. DNA and RNA contains four bases each. Which of the following bases is not present in RNA?
(i) Adenine (ii) Uracil (iii) Thymine (iv) Cytosine
12. Amino acids are
(i) acidic (ii) basic (iii) amphoteric (iv) neutral
13. An -helix is a structural feature of
(i) Sucrose (ii) Polypeptides (iii) Nucleotides (iv) Starch
14. Peptide linkage is present in
(i) Carbohydrates (ii) Vitamins (iii) Proteins (iv) Rubber
15. Dinucleotide is obtained by joining two nucleotides together by phosphodiester linkage. Between
which carbon atoms of pentose sugars of nucleotides are these linkages present?
(i) 5 and 3 (ii) 1 and 5 (iii) 5 and 5 (iv) 3 and 3
16. Proteins can be classified into two types on the basis of their molecular shape i.e., fibrous
proteins and globular proteins. Examples of globular proteins are :
(i) Fibrin (ii) Keratin (iii) Albumin (iv) Myosin
ANSWER–KEY
Q. No. 1 (a) (b) (c) (d) 2 3 4 5 6 7 8
Ans. (iii) (iii) (i) (iv) (iv) (iii) (ii) (ii) (ii) (iv) iii
Q. No. 9 10 11 12 13 14 15 16
Ans. (ii) (i) (iii) (iii) (ii) (iii) (i) (iii)

130 Chemistry

1. Glucose is oxidized by Br2 water to give : (CBSE Term-1_2022)
CHO COOH COOH COOH
(a) (CHOH)4 (b) (CHOH)4 (c) (CHOH)4 (d) (CHOH)4
COOH CH2OH COOH CH3
Ans. (b)
CHO COOH
Bromine water
(CH–OH)4 (CH–OH)4
[O]
CH2–OH CH2–OH
Gluconic acid
2. Which of the following is fibrous protein ? (CBSE Term-1_2022)

(a) Albumin (b) Keratin (c) Insulin (d) Globin
Ans. (b) Keratin
Examples of fibrous proteins are keratin (present in hair, wool, skilk) and myosin. (present
in muscles).
3. -D-Glucopyranose and -D-Glucopyranose are (CBSE Term-1_2022)
(a) Isomers which differ in configuration at C-5
(b) Geometrical isomers
(c) Functional isomers
(d) Anomers
Ans. (d)
The two cyclic hemiacetal forms of glucose differ only in the configuration of the –OH group of
C-1, called anomeric carbon. Such isomers i.e. -forms and -form, are called Anomers.
4. Two among the three components of DNA are 2-deoxyribose and a nitrogen containing node06\B0BB-BC\Kota\Board Material\Chemistry\Booklet\CBSE\Booklet Final_2022-23\Part-2\OC\14_Biomolecules
heterocyclic base. The third component is : (CBSE Term-1_2022)

(a) D-ribose (b) Thymine (c) Guanine (d) Phosphoric acid
Ans. (d)
The components of DNA are
Pentose sugar + Nitrogenous base + Phosphoric acid
5. Which one among the following bases is usually not present in RNA ? (CBSE Term-1_2022)
(a) Uracil (b) Thymine (c) Adenine (d) Guanine
Ans. (b)
Base present in DNA AGCT
Base present in RNA AGCU

CBSE 131
6. Glucose on reaction with (CH3CO)2O forms glucose pentaacetate which confirms the presence of :
(a) –CHO group (b) –COOH group
(c) Five –OH groups (d) A straight chain
Ans. (c)
CHO O O CHO O
(CH–OH)4 + 5CH3 –C–O – C– CH3 (CH–O–C–CH3)4 + 5CH3 COOH
O
CH2–OH
CH2–O–C–CH3
Glucose penta acetate
Glucose react with acetic an hydride to form glucose penta acetic which shows that of a glucose
moleculer contain five –OH groups.
7. Name the unit formed by the attachment of a base to 1 position of sugar.
(CBSE Compartment 2021)
Ans. Nucleoside
8. Define vitamins and classify them on the basis of their solubility. [2]
OR
Define proteins and classify them on the basis of their molecular shape. [2]
(CBSE Compartment 2021)
Ans. On the basis of their solubility in water or fat, vitamins are classified into two groups.
(i) Fat-soluble vitamins : Vitamins that are soluble in fat and oils, but not in 'water, belong to
this group. For example: Vitamins A, D, E, and K
(ii) Water-soluble vitamins : Vitamins that are soluble in water belong to this group. For
example : B group vitamins (B1, B2, B6, B12, etc.) and vitamin C
However, biotin or vitamin H is neither soluble in water nor in fat.
Vitamin K is responsible for the coagulation of blood.
OR
Proteins : These are macro molecules made up of amino acids joined by amide linkage is called
as peptide linkage. These are required for growth and development of the body.
On the basis of their moleculer shape, proteins are of two types.
(A) Fibrous Protein
(i) Polypeptide chains run parallel or anti- parallel and held together by hydrogen and
disulphide bonds.
(ii) Generally insoluble in water e.g., keratin, collagen, myosin, fibroin.
(B) Globular Protein
(i) Chains of polypeptide coil around to give a spherical shape.
(ii) Usually soluble in water, eg. insulin, thyroglobin, albumin, haemoglobin and fibrinogen
gets converted into fibrous protein fibroin on clotting of blood.

132 Chemistry
9. Define the following with an example of each : (CBSE 2018)

(a) Polysaccharides
(b) Denatured protein
(c) Essential amino acids
OR
(a) Write the product when D-glucose reacts with conc. HNO3.
(b) Amino acids show amphoteric behaviour. Why ?
(c) Write one difference between -helix and -pleated structures of proteins.
Ans. (a) Polysaccharides The compound that have large no. of monosaccarides unit on hydrolysis.
Eg Starch, Cellulose etc.
(b) Denatured protein Due to the change in temperature on pH secondary & tertiary
structure are destroyed but primary structure remain intact.
Ex Coagulation of egg white on boiling
(c) Essential amino acids The amino acids which cannot be synthesised in the body & must
be obtanied through diet.
Eg Valine, Leucine
OR
(a)
(b) The amino acids contains both acidic –COOH group & basic –NH2 (amino) group in their
structure, due to which they can exist both as acid & base, this nature is called Amphoteric
nature
O
R – CH – C – OH ( -amino acid)
NH2
:
(c) In -helix, a polypeptide chain form by all possible hydrogen bonds by twisting into a right
handed helical structure with –NH group of each amino acid.
In -pleated all peptide chains are stretched out to nearly extensions & then laid side by side
which are held together by intomolecular hydrogen bonding.

CBSE 133
1. What is the difference between acidic amino acid and basic amino acid ? [1]
2. What type of bonding provides stability to -helix structure of protein ? [1]
3. What type of linkage is present in Nucleic acids ? [1]
4. Write the two types of secondary structures of proteins ? [2]
5. Write one difference between -helix and -pleated structures of proteins. [2]
6. Amino acids show amphoteric behaviour. Why ? [2]
7. What are essential and non-essential amino acids? Name one of each type. [2]
8. Write the main structural difference between DNA and RNA. Of the four bases, name those
which are common to both DNA and RNA. [3]
9. What is essentially the difference between -glucose and -glucose ? What is meant by pyranose
structure of glucose ? [3]
10. What happens when D-glucose is treated with the following regents ? [3]
(i) HI
(ii) Bromine water
(iii) HNO3
11. Define the following terms: [5]
(i) Nucleotide
(ii) Anomers
(iii) Native protein
(iv) Denatured protein
(v) Essential amino acids

134 Chemistry
MOCK TEST SOLUTIONS

1. In acidic amino acid more carboxyl groups as compared to amino groups are present & In basic
amino acid more number of amino than carboxyl groups are present.
2. Hydrogen bonding
3. Phosphodiester linkage
4. -Helix and -pleated sheets.
5. In -helix, a polypeptide chain form by all possible hydrogen bonds by twisting into a right
handed helical structure with –NH group of each amino acid.
In -pleated all peptide chains are stretched out to nearly extensions & then laid side by side
which are held together by intermolecular hydrogen bonding.
6. The amino acids contains both acidic –COOH group & basic –NH2 (amino) group in their
structure, due to which they can exist both as acid & base, this nature is called Amphoteric nature
O
R – CH – C – OH ( -amino acid)
NH2
7. Essential amino acids : The amino acids which cannot be synthesised in the body and must be
obtained through diet, are known as essential amino acids.
Example: Valine, Leucine.
Non-essential acids : The amino acids, which can be synthesised in the body are known as non-
essential amino acids.
Example : Alanine, Aspartic acid.
8. DNA is double stranded -helix structure in which two strands are coiled spirally in opposite
directions.
RNA has single stranded -helix structure. DNA contains four bases namely, adenine (A),
guanine (G), cytosine (C) and thymine (T).
9. The six membered cyclic structure of glucose is called pyranose structure.
6
6 CH2 OH
CH2 OH O
O H 5
OH
H 5 H H
H 4 1
4 1
OH H OH OH H
HO 3 2 HO 3 2 H
H OH H OH
– D glucose – D glucose

CBSE 135
10. (i) On prolonged heating with HI, D-glucose forms n-hexane.
CHO
HI,
(CHOH) 4 CH3–CH2–CH2–CH2–CH2–CH3
n-Hexane
CH2OH
D-Glucose
(ii) D-glucose gets oxidised to six carbon carboxylic acid (gluconic acid) on reaction with
brominewater
CHO
Br2 water
(CHOH)4 COOH
CH2OH (CHOH)4
D-glucose CH2OH
Gluconic acid
(iii) On oxidation with nitric acid, D-glucose yields a saccharic acid.
CHO COO
HNO3
(CHOH)4 (CHOH)
Oxidation
CH2OH COO
D-glucose D-saccharic
11. (i) A unit formed by the combination of nitrogenous base, sugar and phosphate.
(ii) -D-glucose and -D-glucose which have configuration isomer at C1 carbon is known as
Anomers
(iii) Protein found in biological system with unique three dimesion structure and biological
activity is called native protein.

(iv) Denatured protein Due to the change in temperature on pH secondary & tertiary structure
are destroyed but primary structure remain intact.
Ex Coagulation of egg white on boiling
(v) Essential amino acids are required by the human body, but they cannot be synthesised in the
body.
They must be taken through food. For example : valine and leucine

136 Chemistry
IMPORTANT NOTES
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 137
CHEMICAL TEST
I. Primary, Secondary and Tertiary alcohol
Test 1º Alcohol 2º Alcohol 3º Alcohol

(i)
(1) Add Lucas reagent No change Turbidity appears Turbidity appears
Anhyd. ZnCl
ZnCl22 + Conc. HCl within 5 minutes immediately
(ii) Carbonic compound + Lucas reagent

Test Propan-1-ol Propan-2-ol
OH
CH3CH2CH2OH CH3–CH–CH3
(1) Lucas Test No change Turbidity appears within
Add Lucas Reagent 5 minutes.
(Anhydrous ZnCl2 + HCl)
(2) Iodoform Test No change Yellow precipitate of CHl3
Add I2 / NaOH
(iii)
Test Ethanol Propan-2-ol
(1) Add Lucas Reagent

No change Tubidity within 5 minutes
ZnCl2 + HCl)
(Anhydrous ZnCl2
(iv) Test Enthanol  C2H5OH  Pr opan  1  ol  CH3CH 2CH 2OH 

(1) Add I2 / NaOHand heat Yellowiodo / form  CHl3  Nochange
(v) Test Ethanol  CH3CH2OH  Methanol  CH3OH 

(1) Add I2 / NaOHand heat Yellow procipitateof CHI3 Nochange
(2) Addsalicylicacid Pleasant odour Odour of oilof wint er green
II. Difference between Alcohol and Phenol

(i) OH
Test Ethanol
Ethanol CH3CH2OH Phenol
(1) Add I2 / NaOH and heat Yellow ppt. of CHl3 No change

(2) Add neutral FeCl3 No change Violet Colouration

138 

(ii) OH
Propan-2-ol
Test Phenol
CH3–CH(OH)CH3
(1) Add Neutral FeCl3 Violet colour No change

(2) Add Br2 / H2O colour of Br2 decolourised No change
OH
III. Difference OH
between Alkyl Halide and Aryl Halide
Br Br
(i) H3 O Cl
+ 3Br
–3HBr
Test Chloroethane (C2H5Cl) Chlorobenzene
Br
(1) Add aq NaOH + AgNO3 (Colourless)
No change
White precipitate of AgCl
soluble in Ammonia
(ii)
Test Chloroethane CH3CH2Cl Bromoethane CH3CH2Br
(1) Add aq NaOH + AgNO3 White ppt (AgCl) Creamy yellow ppt (AgBr)
(2) Add NH3 in both test tube White ppt get dissolved Yellow ppt dissolved partly
in NH3 in NH3
(iii) CH2Cl Cl
Test Benzyl chloride Chlorobenzene
(1) Add aq NaOH + AgNO3 White ppt soluble in No change

Ammonia
IV. Difference between Aldehyde and Ketone

(i) O
Test Acetaldehyde CH3CHO Acetone H3C–C–CH3
(1) Brown red precipitate
(1)Add
AddFehling's
Fehling'sreagent
reagent Brown red precipitate No
No change
change
(2) Add
CH3Tollen's
CHO + 2Cureagent
2+
+ 5OH CH3COO + Cu2O (red brown)No
– Silver mirror + 3H2O
change
(2) Add Tollen's test Silver mirror No change
(ii)
Test Acetaldehyde CH3CHO Formaldehyde HCHO
(1) Add I2/NaOH and head Yellow ppt. iodoform (CHI3) No Change
(2) Add KMnO4/H2SO4 Smell of vinegar Efferescence of CO2

 139
(iii)
Test Ethanal (CH3CHO) Benzaldehyde (C
(C66H65CHO)
CHO)
(1) Add I2/NaOH Yellow iodoform (CHI3) No change

(2) Add Fehling's reagent Red ppt of Cu2O No change
(iv)
Test Pentan-2-one
Pentan-3-one Pentan-3-one
O O
CH3–C–CH2CH2CH3 CH3CH2–C–CH2CH3
(1) Add I2/NaOH and heat Yellow ppt. (CHI3) No change
O
4NaOH + 3I2 + CH3 – C – CH2CH2CH3 CHI2 + CH3CH2CH2COONa + 3NaI + 3H2O
(v) Acetophenone Benzophenone
Test (Yellow ppt.)
COCH3 O
C
(1) Add I2 / NaOH Yellow iodoform

Yellow iodoform(CHI3) No
Nochange
Change
(1) Add I2/NaOH
(CHI
COCH 3)3 COONa
(2) Add NaHSO3 White ppt No
4NaOH + 3I2 + CHI3 + + 3NaIChange
+ 3H2O
V. Difference between Different-Different Carboxylic Acid
(2) Add NaHSO3 White ppt No change
O OH
(i)
Test Formic3 
C–CH3 + NaHSO acid (HCOOH) C–SO3– Na+ Acetic acid (CH3COOH)
CH3
(1) Tollen's reagent Silver mirror (Ag) No change
HCOOH + [Ag(NH3)2]+ + 2OH  CO2 + Ag + 2H2O + 2NH3

VI. Difference between Phenol and Carboxylic Acid
(i) Phenol (White solid) Benzoic acid (White solid)

Test
OH COOH
(1) Add neutral FeCl3 Violet colour No change

(2) Add NaHCO3 (aq) No change Effervescence of CO2
C6H5COOH + NaHCO3 C6H5COONa + CO2 + H2O
VII. Difference between Primary, Secondary and Tertiary Amine
(i) Test Primary Amine Secondary Amine Tertiary

Amine
Hinsberg reagent White ppt soluble White ppt soluble No Change
C6H5SO2Cl in NaOH in NaOH

140 

(ii)
Test Methanamine Dimethyl Amine
(CH3NH2) (CH3NHCH3)
(1) Add Hinsberg reagent White ppt (soluble White ppt insoluble in
C6H5SO2Cl in NaOH) NaOH (aq.)
(2) Add CHCl3 + KOH(alc.) Four odour of No change
isocyanide
(iii) NH2 NHCH3
Test Aniline N-methyl-aniline
(1) Add Hinsberg reagent White ppt solution in White ppt insoluble in
(C6H5SO2Cl) NaOH NaOH
(2) Add CHCl3 + KOH Foul odour of No change
   C6H5SO2 N – Na
–
OH
C H SO
(alc) 6 5 2 Cl + H2 NC H
6 5 C H
6 5 SO
isocyanide2 NHC H
6 5 NaOH
VIII. Difference between Aliphatic and Aromatic C6H5

(i) NHof
(2) Add CHCl3 + KOH (alc) Foul odour 2 isocyanide No change
NHTest
2
Aniline N  C Methylamine (CH3NH2)
+ HCCl3 + 3KOH  + 3KCl + 3H2O
(1) Add Br2/H2O Colour of Br2 (aq.) No change
decolourised
NH2 IX. Difference
NH between Ketone and Carboxylic Acid
2
(i) Br Br
+ 3Br2(aq)  + 3HBr
Test CH3COCH3 acetone acetic acid CH3COOH
Br (Colourless)
(1) Add l2/NaOH + heat Yellow iodoform (CHI3) No change
(2) Add NaHCO3 No Change Effervescence of CO2
4NaOH + 3l2 + CH3COCH3  CHI3 + CH3COONa + 3Nal + 3H2O
(ii)
Test acetaldehyde CH3CHO acetic acid CH3COOH
(2) Add NaHCO3 No change Effervescence of CO2
3COOH + NaHCO3  CH3COONa + H2O +

(1) CH
Add Fehling's reagent Red ppt. of Cu2OCO2 No change
(2) Add Tollens' reagent Silver mirror (Ag) No change
(3) Add NaHCO3 No change Effervescence of CO2
(iii)
NH2 NH2
Test
(Aniline)
Cyclohexylamine
(1) Add NaNO2 and HCl and N2 gas is liberated and no Stable diazonium salt is formed
then add phenol in colouration is observed. which reacts with phenol to form
presence of a base. orange dye.

 141
NAME REACTIONS
1. Sandmeyer Reaction :
The Cl , Br and CN nucleophiles can easily be introduced in the benzene ring of benzene
diazonium salt in the presence of Cu(I) ion. This reaction is called Sandmeyer reaction.
2. Gatterman Reaction :
Chlorine or bromine can be introduced in the benzene ring by treating the benzene diazonium
salt solution with corresponding halogen acid in the presence of copper powder. This is referred
as Gatterman reaction.
Cu/HCl
ArCl + N2 + CuX
+ –
ArN2X
Cu/HBr ArBr + N2 + CuX
Note : The yield in Sandmeyer reaction is found to be better than Gattermann reaction.
3. Balz-Schiemann Reaction :
When benzenediazonium chloride is treated with fluoroboric acid, benzene diazonium
fluoroborate is precipitated which on heating decomposes to yield aryl fluoride.
 
Ar N 2 Cl   HBF4 
 Ar  N 2 BrF4 
Heat
 Ar  F  BF3  N 2
Fluoroboric acid
4. Finkelstein Reaction :
Alkyl iodides are often prepared by the reaction of alkyl chlorides/ bromides with NaI in dry
acetone. This reaction is known as Finkelstein reaction.
R – X + NaI  R – I + NaX
(X = Cl, Br)
Note : This reaction in forward direction can be favoured by precipitating NaX formed in dry
acetone (according to Le Chatelier’s principle)

142 

5. Swarts Reaction : Heating an alkyl chloride/bromide in the presence of a metallic fluoride such
as AgF, Hg2F2, CoF2 or SbF3 gives alkyl fluorides. The reaction is termed as Swarts reaction.
H3C – X + AgF  H3C – F + AgX
(X = Cl, Br)
Note : Finkelstein Reaction and Swarts Reaction are known as halogen exchange reaction.
6. Wurtz Reaction : Alkyl halides react with sodium in dry ether to give hydrocarbons containing
double the number of carbon atoms present in the halide. This reaction is known as Wurtz
reaction.
CH3Br  2Na  BrCH3 
dry ether
 CH3  CH3  2NaBr
Bromomethane Ethane
C2 H5Br  2Na  BrC2 H5 
dry ether
 C2 H5  C2 H5
Bromoethane n  Butane
7. Wurtz-Fitting Reaction : A mixture of an alkyl halide and aryl halide gives an alkylarene when
treated with sodium in dry ether and is called Wurtz-Fitting reaction.
X R
Ether
+ Na + RX + Na X
8. Fitting Reaction : Aryl halides also give analogous compounds when treated with sodium in dry
ether, in which two aryl groups are joined together. It is called Fitting reaction.
X
Ether
2 + Na + 2NaX
9. Friedel-Crafts alkylation Reaction : When benzene is treated with an alkyl halide in the
presence of anhydrous aluminium chloride, alkylbenene is formed.
CH3
Anhyd. AlCl 3
+ CH3Cl + HCl
Toluene
(13.75)
C2H5
Anhyd. AlCl 3
+ C2H5Cl + HCl
Ethylbenzene
Cl Cl Cl
CH3
Anhyd. AlCl3
+ CH3Cl
1-Chloro-2-methylbenzene CH3
(Minor)
1-Chloro-4-methylbenzene
(Major)
OCH3 Cl OCH3
CH3
Anhyd. AlCl3
+ CH3Cl CS2 +
2-Methoxytoluene CH3
(Minor)
4-Methoxytoluene
(Major)
Note : Aromatic carboxylic acids do not undergo Friedel-Crafts reaction because the carboxyl
group is deactivating and the catalyst aluminium chloride (Lewis acid) gets bonded to the
carboxyl group.

 143
10. Friedel-Crafts acylation reaction : The reaction of benzene with an acyl halide or acid
anhydride in the presence of Lewis acids (AlCl3) yields acyl benzene.
COCH3
Anhyd. AlCl3
+ CH3COCl  + HCl
Acetylchloride
Acetophenone
COCH3
Anhyd. AlCl3
+ (CH3CO)2O  + CH3COOH
Acetic anhydride
Cl Cl O Cl
O
Anhyd. AlCl3 CH3
+ H3C–C–Cl +
2-Chloroacetophenone
(Minor) O CH3
4-Chloroacetophenone
(Major)
OCH3 OCH3 OCH3

COCH3
Anhyd. AlCl3
+ CH3COCl +
Ethanoyl
chloride 2-Methoxy- COCH3
acetophenone
4-Methoxy-
(Minor)
acetophenone
(Major)
11 Reimer-Tiemann Reaction : On treating phenol with chloroform in the presence of sodium
hydroxide, a –CHO group is introduced at ortho position of benzene ring resulting
salicylaldehyde. This reaction is known as Reimer - Tiemann reaction.
– –
OH O Na+ O Na+ OH
CHCl2 CHO CHO
CHCl3 + aq NaOH NaOH H+
Intermediate Salicylaldehyde
12. Kolbe’s Reaction : Phenol with sodium hydroxide gives sodium phenoxide ion which with
carbon dioxide in acidic medium results hydroxybenzoic acid (salicylic acid). This is known as
Kolbe’s reaction.
OH ONa OH
COOH
NaOH (i) CO2
(ii) H+
(Salicylic acid)

144 

13. Rosenmund Reduction : Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium
on barium sulphate. This reaction is called Rosenmund reduction.
O
C CHO
Cl H2
Pd – BaSO4
Benzoyl chloride Benzaldehyde
14. Stephen reaction :


RCN  SnCl 2  HCl 

 RCH  NH 
H3 O
 RCHO
Nitriles are reduced to corresponding imine with stannous chloride in the presence of
hydrochloric acid, which on hydrolysis give corresponding aldehyde. This reaction is called
Stephen reaction.
15. Etard reaction : Chromyl chloride oxidizes methyl group to a chromium complex, which on
hydrolysis gives corresponding benzaldehyde. This reaction is called Etard reaction.
CH3 CH(OCrOHCl2)2 CHO
CS2 H3O+
+ CrO2Cl2
Toluene Chromium complex Benzaldehyde
16. Gatterman Koch Reaction : When benzene or its derivative is treated with carbon monoxide
and hydrogen chloride in the presence of anhydrous aluminium chloride or cuprous chloride, it
gives benzaldehyde or substituted benzaldehyde. This reaction is known as Gatterman-Koch
reaction.
CHO
CO, HCl
Anhyd. AlCl3/CuCl
Benzene Benzaldehyde
17. Clemmensen Reduction : The carbonyl group of aldehydes and ketones is reduced to CH2
group on treatment with zinc- amalgam and concentrated hydrochloric acid. This is known as
Clemmensen reduction.
Zn-Hg
C=O CH2 + H2O (Clemmensen reduction)
HCl
18. Wolff Kishner Reduction : The carbonyl group of aldehydes and ketones is reduced to CH2
group on treatment with hydrazine followed by heating with sodium or potassium hydroxide in
high boiling solvent such as ethylene glycol. This is known Wolff Kishner reduction.
NH2NH2 KOH/ethylene glycol
C=O C=NNH2 CH2 + N2
–H2O heat
(Wolff-Kishner reduction)

 145
19. Tollens’ test : On warming an aldehyde with freshly prepared ammoniacal silver nitrate solution
(Tollens’ reagent), a bright silver mirror is produced due to the formation of silver metal. The
aldehydes are oxidised to corresponding carboxylate anion. The reaction occurs in alkaline
medium.
 
RCHO  2[Ag(NH3 )2 ]  3OH 
 RCOO  2Ag  2H2O  4NH3
Silver Mirror
20. Fehling’s test : Fehling reagent comprises of two solutions, Fehling solution A and Fehling
solution B. Fehling solution A is aqueous copper sulphate and Fehling solution B is alkaline
sodium potassium tartarate (Rochelle salt). These two solutions are mixed in equal amounts
before test. On heating an aldehyde with Fehling’s reagent, a reddish brown precipitate is
obtained. Aldehydes are oxidised to corresponding carboxylate anion. Aromatic aldehydes do
not respond to this test.
 
R  CHO  2Cu2   5O H 
 RCO O  Cu2 O  3H 2O
Re d  brown ppt
21. Aldol reaction : Aldehydes and ketones having at least one a-hydrogen undergo a reaction in the
presence of dilute alkali as catalyst to form b-hydroxy aldehydes (aldol) or b-hydroxy ketones
(ketol), respectively. This is known as Aldol reaction. The name aldol is derived from the names
of the two functional groups, aldehyde and alcohol, present in the products.
(i) Aldol condensation : The aldol and ketol readily lose water to give a, b-unsaturated carbonyl
compounds which are aldol condensation products and the reaction is called Aldol
condensation.
dil. NaOH
2 CH3–CHO CH3–CH–CH2–CHO  CH3–CH=CH–CHO
Ethanal –H2O But-2-enal
OH (Aldol condensation product)
(Aldol)
3-Hydroxybutanal
(ii) Cross aldol condensation : When aldol condensation is carried out between two different
aldehydes and / or ketones, it is called cross aldol condensation. If both of them contain a-
hydrogen atoms, it gives a mixture of four products.
CH3CHO 1. NaOH CH3–CH=CH–CHO + CH3CH2–CH=C–CHO
+ 2.  But-2-enal
CH3CH2CHO CH3
CH3–CH=C–CHO + CH3CH2–CH=CHCHO
CH3
2-Methylbut-2-enal Pent-2-enal

146 

22. Cannizzaro reaction : Aldehydes which do not have an -hydrogen atom, undergo self
oxidation and reduction (disproportionation) reaction on treatment with concentrated alkali. In
this reaction, one molecule of the aldehyde is reduced to alcohol while another is oxidised to
carboxylic acid salt.
H O
H H
C=O + C=O + Conc. KOH H–C–OH + H–C
H H OK
H
Methanol Potassium formate
2 CHO + Conc. NaOH CH2OH + COONa
Benzaldehyde Benzyl alcohol Sodium benzoate
23. Kolbe electrolysis : An aqueous solution of sodium or potassium salt of a carboxylic acid on
electrolysis gives alkane containing even number of carbon atoms. It is decarboxylation reaction.
The reaction is known as Kolbe electrolysis.
2CH3COO Na   2H 2O
Sodiumacetate
 Electrolysis
CH3 – CH3  2CO2  H 2  2NaOH
24. Hell-Volhard-Zelinsky (HVZ )reaction : Carboxylic acids having an -hydrogen are

halogenated at the -position on treatment with chlorine or bromine in the presence of small
amount of red phosphorus to give -halocarboxylic acids. The reaction is known as Hell-
Volhard-Zelinsky reaction.
(i) X /Red phosphorus
R–CH2–COOH (ii) H2 O R–CH–COOH
2
X
X = Cl, Br
–Halocarboxylic acid
25. Gabriel phthalimide synthesis : Gabriel synthesis is used for the preparation of pure primary
amines.
Phthalimide on treatment with ethanolic potassium hydroxide forms potassium salt of
phthalimide which on heating with alkyl halide followed by alkaline hydrolysis produces the
corresponding primary amine.

 147
O O O
C KOH C – R–X C
N–H N–R
+
NK
C C C
O O O
Phthalimide N-Alkylphthalimide
O
O
C –
NaOH(aq) C ONa+
N–R – + R – NH2
C ONa+ (1° amine)
C
O
O
Note : Aromatic primary amines cannot be prepared by this method because aryl halides do not
undergo nucleophilic substitution with the anion formed by phthalimide.
26. Hoffmann bromamide degradation reaction : An amide with bromine in an aqueous or
ethanolic solution of sodium hydroxide gives primary amines.
In this degradation reaction, migration of an alkyl or aryl group takes place from carbonyl carbon
of the amide to the nitrogen atom. The amine so formed contains one carbon less than that
present in the amide.
O
R–C–NH2 + Br2 + 4NaOH R–NH2 + Na2CO3 + 2NaBr + 2H2O
27. Carbylamine reaction : Aliphatic and aromatic primary amines on heating with chloroform and
ethanolic potassium hydroxide form isocyanides or carbylamines which are foul smelling
substances. This reaction is known as carbylamines reaction or isocyanide test.
R  NH2  CHCl3  3KOH 
Heat
R  NC  3KCl  3H2O
Note : Secondary and tertiary amines do not show this reaction and is used as a test for primary
amines.
28. Hinsberg’s Test : Benzenesulphonyl chloride (C6H5SO2Cl), which is also known as Hinsberg’s
reagent, reacts with primary and secondary amines to form sulphonamides.
(i) The reaction of benzenesulphonyl chloride with primary amine yields N
ethylbenzenesulphonyl amide. The hydrogen attached to nitrogen in sulphonamide is strongly
acidic due to the presence of strong electron withdrawing sulphonyl group. Hence, it is soluble
in alkali.
O O
S–Cl + H–N–C2H5 S–N–C2H5 + HCl
O H OH
N-Ethylbenzenesulphonamide
(soluble in alkali)

148 

(ii) In the reaction with secondary amine, N,N-diethylbenzenesulphonamide is formed. Since
N, N-diethylbenzene sulphonamide does not contain any hydrogen atom attached to nitrogen
atom, it is not acidic and hence insoluble in alkali.
O O
S–Cl + H–N–C2H5 H3C S–N–C2H5 + HCl
(insoluble in alkali)
O C2H5 O C2H5
N,N-Diethylbenzenesulphonamide
(iii) Tertiary amines do not react with benzenesulphonyl chloride.

Note : This test is used for the distinction of primary, secondary and tertiary amines and also for
the separation of a mixture of amines. However, these days benzenesulphonyl chloride is
replaced by p-toluenesulphonyl chloride.
29. Coupling Reactions : Benzene diazonium chloride reacts with phenol in which the phenol
molecule at its para position is coupled with the diazonium salt to form p-hydroxyazobenzene.
This type of reaction is known as coupling reaction.
–
+ – OH
NN Cl + H OH N=N OH + Cl– + H2O
p-Hydroxyazobenzene (orange dye)
Similarly the reaction of diazonium salt with aniline yields p-aminoazobenzene.

–
+ – OH
NN Cl + H NH2 N=N NH2 + Cl– + H2O
p-Aminoazobenzene
(yellow dye)

Chemistry Part - 2

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"This booklet is colour coded for you convenience.

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HALOALKANES AND HALOARENES : (CHAPTER-10)

Alkyl halides Alkenyl halides Alkynyl halides Aryl haides

Mono halides Di-halides Tri-halides Tetra halides

Primary halides Secondary halides Tertiary halides

R—OH + PCl5 R—Cl + POCl3 + HCl

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Chemical Properties of Alkyl halide :

B = Base ; X = Leaving group

Reaction with sodium (Wurtz reaction)

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The process of conversion of enantiomers into a racemic mixture is known as racemisation.

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EXERCISE-1 INTEXT QUESTIONS

(i) + SOCl2 (ii) O2N UV light

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Ans. (i) 2-Chloro-2-methylpropane (3°) 3° more stable

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7. Write IUPAC names of the following :

Ans. (i) 4-Bromopent-2-ene (ii) 3-Bromo-2-methylbut-1-ene

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(i) H + HBr (ii) CH3–CH2–CH = CH2 + HCl

CH2– CH2– CH2– Br

Ans. (i) (ii) CH 3 CH 2 – CH CH3 (iii)

CH2Cl and Cl ; and

I As iodine is a better leaving group because of its large size, it will be

(i) The four isomeric bromobutanes

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EXERCISE-2 NCERT EXERCISE

3. How will you bring about the following conversion ?

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KOH (alc)/ –HBr

Ans. (i) CH 3 CH 2 CH 2 I (ii) CH3–C = CH2

(iii) CH 3CH OH CH 2 CH3 (iv) CH3 CH 2 CN

(v) C6 H 5 O C2 H 5 (vi) CH 3 CH 2CH 2 Cl

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The given reaction is an SN2 reaction.

C3H5 C3H 5 C3H5

CH3CH2CH2CH2CH2 – Br > CH3CH2CH2CHCH3 > CH3CH2CCH3

(ii) CH3CHCH2CH2Br > CH3CHCHCH3 > CH3CCH2CH3

CH3–CH2–CH2–CH2–Br CH3– CH–CH2–CH2–Br

1-Bromo-2-methylbutane (1°) 1-Bromo-2, 2-dimethylpropane

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Propene addition) Propan-1-ol

CH3 CH2Cl CH2–OH

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(i) n-butyl chloride is treated with alcoholic KOH,

(ii) bromobenzene is treated with Mg in the presence of dry ether,

(iii) chlorobenzene is subjected to hydrolysis,

(iv) ethyl chloride is treated with aqueous KOH,

(vi) methyl chloride is treated with KCN.

(iv) CH 3 CH 2 OH (v) CH 3 CH3 (vi) CH 3 CN

12. The following compounds are given to you :

(i) +Br2 UV light

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Ans. (i) Inversion of configuration

17. What happens when

Write chemical equations in support of your answer.

(iii) CH3Cl + KNO2 CH3–ONO + KCl