GRADE-XII CHEMISTRY WORKSHEET

ORGANIC CHEMISTRY
IMPORTANT QUESTIONS

Q1. Complete the following :

(A) Hydrocarbons and halogen derivatives.
(i) CH3CH2CH = CH2 + HBr (AI 2009, Foreign 2011)
Peroxide
(ii) CH3CH2CH = CH2 + HBr (Delhi 2008)
CCl4
(iii) CH2 = CH2 + Br2 (Delhi 2008, AI 2008)
(iv) C6H5N2Cl + KI
H H
C=C + HBr
H
(v) (Foreign 2011)

Heat
(vi) (CH3)3CBr + H2O
Heat
(vii) CH3CH2Cl + SbF3
Liq. NH3
(viii) CH3CH2C ≡ CNa + CH2 = CHCH2Br
CH3
CH
CH3
(ix) + Br2 heat

OH
red P
(x) I2

(xi) CH3CH2Cl + KNO2 Two products

Br C2H5ONa
(xii) CH C2H5OH
3

(xiii) heat (Delhi 2012C)

+ Br2
light
 OH

(xiv) + HCl

CH2OH
CH3
(xv) + HI (Delhi 2012C, AI 2009, Foreign 2011)

(xvi) CH3CH = CHCH2Cl + CN– (A) + (B) (2012C)

(B) Alcohols, phenols and ethers.

(i) OH + SOCl2 (Delhi 2009)

(ii) CH2OH (Delhi 2009)

+ HCl
HO
(iii) OC2H5 + HBr (Foreign 2012)

(iv) (CH3)3C – O – C2H5 + HI (Foreign 2012)

(v) CH3CH2CH2OCH3 + HBr (Foreign 2012)

(vi) + HI

(C) Aldehydes, ketones and carboxylic acids.

2+
Hg
(i) CH3C ≡ CH (Delhi 2012)
H2SO4
O3
(ii) ..... 2 O (Delhi 2008, AI 2011)
H 2O

(iii) CH2 CHO (Delhi 2008, AI 2011)

CH3

(i) CrO2Cl2
(iv) +
(Delhi 2012)
(ii) H3O

NO2
 COCH3
anhy. AlCl3
(v) + ..... (Delhi 2009)

O
C
(vi) + ..... ..... (Delhi 2009)

anhy. AlCl3
(vii) + C2H5COCl CS2

(Delhi 2011C, 2012, AI 2012C)

O
CH3 +
(viii) + CH3CH2NH2
H
(AI 2011C)

H2NCONHNH2
(ix) C6H5CHO (AI 2011)
Conc. KOH
(x) C H (Delhi 2013)
O –
OH
(xi) C6H5CHO + C6H5COCH3 (Delhi 2011C)
293 K
Zn Hg
(xii) C CH3 (AI 2013)
Conc. HCl
O
H2
(xiii) C6H5–COCl (Delhi 2009A, 2011C, AI 2013)
Pd BaSO4
O
CH3
(xiv) H2CrO4 (AI 2011C)

CHO

HNO3/H2SO4
(xv) (Delhi 2013)
273-283 K

CH2CH3
KMnO4
(xvi) ......
KOH, heat
(Delhi 2008, 2011, Foreign 2011)
 KMnO4
(xvii) (AI 2011C)
H2SO4, heat

COOH
SOCl2
(xviii) (Delhi 2011, AI 2011, Foreign, 2011)
heat
COOH
Br2/P
(xix) CH3COOH (Delhi 2013)
COOH

Br2/FeBr3
(xx) (AI 2013)

O
LiAlH4
(xxi) R NH2 (AI 2009)
H 2O
+
H 3O
(xxii) C6H5CONH2 (AI 2009)
heat
O
Br2 + NaOH
(xxiii) CH3 NH2 (Delhi 2011, Foreign 2011)
O
(xxiv) O + NaBH4
CH2 OCH3
(D) Amines.
(i) C2H5NH2 + C6H5SO2Cl (AI 2009)
(ii) C6H5NH2 + CH3COCl (AI 2009)
(iii) C2H5NH2 + HNO2 (AI 2009)
(iv) RNH2 + CHCl3 + KOH (Delhi 2010, AI 2013)
(v) C6H5NH2 + Br2 (aq.)
(AI 2009, 2012, 2013, Foreign 2012)
(vi) C6H5NH2 + HCl (aq.) (AI 2013)
(vii) C6H5N2Cl + KI ........ (Delhi 2008)
(viii) Diazonium group + –I (Delhi 2008, AI 2008)
(ix) C6H5N2Cl + H3PO2 + H2O
(AI 2009, 2012, Foreign 2012, AI 2013)
(x) C6H5N2Cl + CH3CH2OH (Delhi 2010)
 5

(xi) C6H5N2Cl + C6H5NH2 OH

(Delhi 2010)
H 2O
(xii) C6H5N2+ Cl– (AI 2013)
room temp.

Q2. Identify the missing compounds (reagents) in the following:

NaCN Reduction
(i) C2H5Cl A Ni/H2
B (AI 2010)

KCN LiAlH4 HNO2

(ii) CH3CH2Br A B C (AI 2013)
0°C
NaNO2 C6H5NH2
(iii) C6H5NH2 A B (AI 2010)
HCl OH
+
CuCN H2O/H NH3
(iv) C6H5N2+Cl– A B heat
C (Delhi 2013)
+
Sn + HCl NaNO2 + HCl H2O/H
(v) C6H5NO2 A B C
273 K heat
(Delhi 2013)
NH3 NaOH + Br2 CHCl3
(vi) CH3COOH
∆
A B C (AI 2013)
alc. KOH

(i) C2H5MgCl Conc. H2SO4 HBr

(vii) CH3CHO A B C
(ii) H2O peroxide
(Delhi 2011C)
(viii)

(AI 2008C)
(ix)

(AI 2009C)
COOH
Heat strong
(x) + NH3 A B heating C
COOH
(AI 2011C)
6

COOH

Conc. HNO3 SOCl2 (i) NaBH4

(xi) A B + C
Conc. H2SO4 (ii) H3O

SOCl2

H2, Pd, BaSO4

D E
S or quinoline

CH3
273-278 K
(xii) + CrO3 + (CH3CO)2O A
+
H3O , heat

KMnO4, KOH, B
heat
Conc. NaOH
D
+
COONa
H3O
C +
E
(AI 2010C)
 SOLUTION

(A) Hydrocarbons and halogen derivatives.

Mark. addition
1. (i) CH3CH2CH = CH2 + HBr CH3CH2CHCH3
|
Br
Peroxide
(ii) CH3CH2CH = CH2 + HBr CH3CH2CH2CH2Br
anti-markow.
addition
CCl4
(iii) H2C = CH2 + Br2 BrCH2 – CH2Br
(iv) C6H5N2Cl + KI C6H5I + N2 + KCl
H H
C
(v) H
Br H

(vi) (CH3)3COH
Heat
(vii) 3CH3CH2Cl + SbF3 3CH3CH2F + SbCl3
(viii) CH3CH2C ≡ CCH2CH = CH2

(ix) ( )

OH I
(x) red P
I2

O
(xi) CH3CH2Cl + KNO2 N + CH3CH2 O N=O
O
Nitroethane Ethyl nitrite
Br CH3
C2H5ONa/C2H5OH
(xii) CH3 ( HBr)

1-Methylcyclohexene
Br

(xiii)

3-Bromocyclohexene
 In presence of heat and light, allylic bromination takes place, while
in dark bromine adds on double bond to form dibromoderivative.
OH

HCl reacts with alcohols (–CH2OH) and not

(xiv)
with phenols.

CH2Cl
CH3
(xv) I HI adds according to Markownikof’s rule.

(xvi) The reactant is allylic compound, so it can form two products.

CH3–CH = CH–CH2Cl CH3CH = CH–CH2 + Cl–
+ +
CH3CH = CH CH2 CH3CH CH = CH2
– –
CN CN

CH3CH = CH CH2CN CH3CH CH = CH2

CN
(B) Alcohols, phenols and ethers.

(i) Cl + SO2 + HCl

(ii) CH2OH CH2Cl

+ HCl + H2O
HO HO
(Phenolic –OH is not easily replaced, hence does not react with
HCl)
(iii) OC2H5 OH
+ HBr + C2H5Br

C6H5–O bond has some double bond character (see below), thus it
is shorter and stronger, and hence difficult to be cleaved.
+
C2H5 C2H5

+
C2H5
 Moreover, C2H5+ is more stable than C6H5+.
+
H
C6H5OC2H5 C6H5O+ C2H5
+
C6H5+ + HOC2H5 C6H5O+C2H5 C6H5OH + C2H5
(less stable) (more stable)

Br

C2H5Br

(iv) (CH3)3C – O – C2H5 + HBr (CH3)3CBr + C2H5OH

(CH3)3C+ (a 3° carbocation) is more stable than the C2H5+, hence
it is easily formed.
(v) CH3CH2CH2OCH3 + HBr CH3CH2CH2Br + CH3OH
+
CH3CH2CH2 is more stable than CH3+ due to inductive effect
(CH3CH2 →– CH2+ ) as well as hyperconjugation.

(vi) + HI CH2I

+ HO
+
CH2

(benzyl carbocation) is more stable due to resonance than

+

(C) Aldehydes, ketones and carboxylic acids.

2+
Hg , H2SO4
(i) CH3C ≡ CH CH3 = CH2 CH3 CH3
(hydration)
OH O
O3
(ii) 2 O
Zn-H2O
In ozonolysis, C=C is always cleaved to C=O + O=C .
B2H6/THF H2O2
(iii) 3 CH2 CH B NaOH
3
 PCC
3 CH2OH 3 CHO

Cyclohexane carbaldehyde

CH3 CHO

(i) CrO2Cl2
(iv)
+
(ii) H3O
(Etard oxidation)
NO2 NO2
COCH3
anhy. AlCl3
(v) + CH3COCl
(Friedel-Craft reaction)

Acetophenone

O
COCl C
anhy. AlCl3
(vi) +
(Friedel-Craft
reaction)
Benzolphenone

COC2H5
anhy. AlCl3, CS2
(vii) + C2H5COCl
(Friedel-Craft
reaction)
Propiophenone

CH3 +
CH3
(viii) O + H2NCH2CH3
H
NCH2CH3

Schiff’s base
+
H
(ix) C6H5CHO + H2NNHCONH2 C6H5CH = NNHCONH2 + H2O
Benzaldehyde semicarbazone
Note that the –NH2 end of –CONH2 does not react because its
O O
H H +
N C N H2 N C = N H2

nucleophilic character is decreased due to resonance.

Conc. KOH
(x) 2H H CH3OH + HCOONa
(Cannizzaro reaction)
Methanol Sod. methanoate
O
 11
–
OH , 293K
(xi) C6H5CHO + H3CCOC6H5 C6H5CH = CHCOC6H5
crossed aldol
Benzaldehyde Acetophenone condensation Benzal acetophenone
Zn–Hg/HCl
(xii) CH3COCH3 CH3CH2CH3
Clemmensen reduction
H2 Pd BaSO4
(xiii) C6H5COCl C6H5CHO
(Rosenmund reduction)
Benzaldehyde

O
CH3 COOH
H2CrO4
(xiv)
(oxidation)

CHO CHO
HNO3/H2SO4
(xv)
273 283 K

NO2
m-Nitrobenzaldehyde
(xvi) Alkyl group present on benzene ring is always oxidised to –COOH
group, irrespective to its length, when oxidised by a strong oxidis-
ing agent.
CH2CH3 COOK
KMnO4
KOH, heat

KMnO4, H2SO4 COOH

(xvii) .......
(Oxidation) COOH
Cyclohexene Hexan-1, 6-dioic acid
(Adipic acid)

COOH COCl
SOCl2
(xviii)
heat
COOH COCl
Phthaloyl chloride
Br2/P
(xix) CH3COOH BrCH2COOH
HVZ reaction
Acetic acid α-Bromoacetic acid
COOH COOH

Br2/FeBr3
(xx)
Br
 O
LiAlH4, H2O
(xxi) R NH2 R – CH2 – NH2
(reduction)
Alkanamide Alkanamine
+
H3O , heat
(xxii) C6H5CONH2 C6H5COOH + NH3
(hydrolysis)
Benzamide Benzoic acid

O
Hofmann
(xxiii) CH3 – C – NH2 + Br2 + 4NaOH
bromamide reaction
CH3NH2 + 2NaBr + Na2CO3 + 2H2O

(xxiv) Sodium borohydride (NaBH4) is a weak reducing agent, hence it

reduces only aldehydes/ketones, but not esters.
O OH
O NaBH4 O
CH2 OCH3 CH2 OCH3
(D) Amines.
1. (i) C2H5NH2 + C6H5SO2Cl C2H5NHSO2C6H5
N-Ethyl benzenesulphonamide

(ii) C6H5NH2 + CH3COCl C6H5NHCOCH3

Acetanilide

(iii) C2H5NH2 + HNO2 C2H5OH + N2 + H2O

(iv) RNH2 + CHCl3 + 3KOH Carbylamine 

N == C + 3KCl + 3H2O
reaction
Alkyl isocyanide
NH2 NH2
Br Br
(v) + Br2 (aq.)

Aniline
Br
2, 4, 6-Tribromoaniline

(–NH2 group is highly activating and aqueous Br2 solution is highly

ionising to give Br+ ions, hence tribromo product is formed)
(vi) C6H5NH2 + HCl (aq.) C6H5NH3+ Cl–
(vii) C6H5N2Cl + KI C6H5I + N2 + KCl
 +
N2Cl I

(viii) + KI + KCl + I2

Benzene diazonium Iodobenzene

chloride
Reduction
(ix) C6H5N2Cl + H3PO2 + H2O C6H6 + N2 + H3PO3 + HCl
Reduction
(x) C6H5N2Cl + CH3CH2OH C6H6 + CH3CHO + N2 + HCl
Benzene
+ OH
(xi) N ≡ + NH2
Coupling reaction

N=N NH2

p-Aminoazobenzene
(azo dye)
H 2O
(xii) C6H5N2+ Cl– C6H5OH + N2 + HCl
room temp.
2.
NaCN Reduction
(i) C2H5Cl C2H5CN C2H5CH2NH2
Ni/H2
(A) (B)

LiAlH4
(ii) CH CH Br KCN
CH3CH2CN CH3CH2CH2NH2
3 2
(A) (B)
HNO2
CH3CH2CH2OH
0°C
(C)
NaNO2 C6H5NH2
(iii) C H NH C6H5N2Cl
6 5 2 HCl OH
(A)

C6H5N = N NH2
(B)
+
+ CuCN H2O/H NH3
(iv) C6H5N2 Cl C6H5CN C6H5COOH
Benzonitrile (A) (B)
heat
C6H5COONH4 C6H5CONH2
Benzamide (C)
 Sn + HCl NaNO2 + HCl
(v) C6H5NO2 C6H5NH2 C6H5N2Cl
273 K
Aniline (A) (B)
+
H2O/H
C6H5OH
heat
Phenol (C)

NH3 ∆
(vi) CH3COOH CH3COONH4 CH3CONH2
(–H2O)
(A)
NaOH + Br2 CHCl3 + alc. KOH 
CH3NH2 CH3N == C
Hofmann (Carbylamine
bromamide reaction Methyl amine reaction) Methyl isonitrile
(B) (C)

OH
(i) C2H5MgCl Conc. H2SO4
(vii) CH3CHO CH C2H5
(ii) H2O
(A)
Br
HBr + peroxide
CH3CH = CHCH3 CH3CHCH2CH3
anti-Mark. addition
But-2-ene (B) 2-Bromobutane (C)
(Major)

(viii)

(ix)
(x)

COOH COOH COCl

Conc. HNO3 SOCl2

(xi)
Conc. H2SO4
NO2 NO2
(A) (B)
SOCl2
(i) NaBH4 NaBH4 does not
COCl + reduce –NO2 gp.
(ii) H O
3

CH2OH

(D)

H2, Pd, BaSO4 + S or quinoline NO2

(Rosenmund reduction) (C)

CHO

(E)
(xii)