O O

|| ||
(c) C 6H 5  C — (d) C 6 H 5  C  NH 2
(e) C6H5–CN

Note: Students should solve this DPPs and following questions of GOC sheet by 6thAugust 06
Exercise I – Q.16, 31,41, 45, 46, 48, 49, 51, 53,
Exercise II– Q.19
Exercise III– Q.6,11, 24, 39, 41, 45, 52,
Exercise IV(A)– Q.9
Exercise IV(B)– Q.1, 4
 (D) it is SN1 reaction at 1° C–Cl bond while SN2 reaction at 3° C–Cl bond
NaI
[Sol. E2 reaction take place when gem-dihalide 
 ]
acetone
Q.350goc Which of the following structure represents the transition state of slow step of reaction III? [2]

(A) (B)

(C) (D*)

Q.451goc Which of the reaction (I – VI) involves rearrangement of reaction intermediate? [2]
(A) III only (B*) III, V (C) II, III, V (D) I, III, V
[Sol. Hybrid shift in III and ring expansion in V]

Q.552goc Planar reactive intermediates are formed in reactions [2]

(A) III, V (B) I, III, V (C) V, VI (D*) I, III, V, VI
[Sol. Because IInd is E2 reaction (one step reaction) and IVth reaction is SN2 (one step reaction)]

Q.621goc How many litres of methane would be produced when 0.6 gm of CH3MgBr is treated with excess of
C4H9NH2 [2]
(A) 0.8 litre (B) 0.08 litre (C*) 0.112 litre (D) 1.12 litre
[Sol. Q 119 gm MeMgBr gives 22.4 lit
22.4
 0.6 gm will give  0.6 = 0.112 lit. ]
119

3 ( i ) CH ONH
Q.799goc 2CH3 MgBr ( 2  [2]
ii ) H 

(A) CH3 –O–NH–CH3 (B) CH3–NH–CH3

(C*) CH3 –NH2 (D) CH3 –O–CH3
[Sol. CH3 MgBr + CH3 ONH2  CH4 + CH3 ONHMgCl


H3O
CH3 OH + CH3 –NH2   CH3NHMgCl + CH3OMgBr ]

Q.8 Heterolysis of CH3CH2CH3 results information of: [2]

(A) CH3 & C2H5 (B*) –:CH3 & +C2H5 (C) +CH3 & –:C2H5 (D) none of these

Q.9 Those compounds which would generate carbenes on exposure to ultraviolet light include: [2]
(A*) CH2N2 (B*) CH2 = C = O (C) CH2I2 (D) CHCl3

H O Mg HCHO
Q.10 3
+ MeMgCl   A HBr
 B  C  
D [2]
Et 2O H 3O
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.-20
TIME : 25 MIN. MAX. MARK : 28
Q.1 1-octene NBS
 ? [1]
Major product in the above reaction is
(A) 3-bromo-1-octene (B) 2-bromo octane
(C) 1-bromo octane (D*) 1-bromo-2-octene
Q.2 On chlorination, an equimolar mixture of ethane and neopentane yields neopentyl chloride and
ethyl chloride in the ratio 2.3 : 1. How does the reactivity of 1° hydrogen in neopentane compare with
that of a 1° hydrogen in ethane? [2]
Q.3 How many possible monochloro products are formed when methylcyclohexane is treated with Cl2 in
presence of Sun light? [2]
Q.4 Addition of small amount of (C2H5)4Pb to a mixture of methene and chlorine, starts the reaction at
140°C instead of the usual minimum 250°C. Why? [2]
Q.5 Complete and propose mechanism [2]

CH2=CH–CHD–CH=CH2  A
Q.6 What happens when cis-5-t-butyl-2-methyl cyclohexanone is kept in very dilute base? [3]
Q.7 Complete the following reactions and write possible products [4]
HCBr Cl HCBr Cl
(i) cis-2-butene  2 (ii) trans-2-butene  2
KOH KOH

Q.8 Write major product of following reaction [4]

PhLi
(a) KOH
 A (b) Ph2C=CH–Cl  B
Br2 

AlCl ( i ) Na
(c) 3  C (d) + 2CHCH    D
HCl,  liq . NH 3
( ii ) H 2O
Q.9 When propane is treated with chlorine in presence of Sunlight two monochloro products A and B are
obtained. Major product A is treated with Bromine in Sunlight to give C as major monobromomonochloro
product. Given structures of A, B and C. Also write mechanism for the conversion of A into C.
[4]
Q.10 Bromination of methane is slowed down by addition of fairly large amount of HBr. [4]
(a) Suggest a possible explanation for this.
(b) Account for the fact that addition of HCl does not have a similar effect upon chlorination of CH4.

Note: Students should solve the following questions of GOC sheet by positively
Exercise I – Q.2 to Q.9, Q.24 to Q.30, Q.32 to Q.36, Q.39, Q.40, Q.47, Q.50, Q.52
Exercise II– Q.1 to Q.5, Q.11 to Q.14, Q.16 to Q.18, Q.20 to Q.22, Q.24 to Q.31
 (I) (II) (III)

(IV) (V)

[Ans.

Also II  D-sugar.
Sugar I, III and IV are all L-sugar
Any pairs of two structures other than II and V are distereomer pair.]

Q.11 Both cis and trans isomers of 3-methoxycyclohexanol are chiral. However, one distereomers reacts with
a base and then with methyl iodide to give an optically inactive compound while the other distereomer
gives a racemic mixture of optically active compound. Explain. [2+2]
[Ans. The cis and trans forms of 3-methoxy cyclohexanol are:

CH I
cis-3-methoxycyclohexanol base
 3
 
SN 2
 Cl
|
[Sol. (1) C–C–Cl, C–C , (2) Cl–C–C–Cl, (3) C  C  Cl , (4) Cl–C–C ,
|
Cl

(5) C–C , (6) Cl–C– , (7) C– , (8) Cl3C–CCl3]

Q.5alkene Pick the correct statement for monochlorination of R-secbutyl chloride. [3]

Cl
2

300C

(A) There are four possible production ; three are optically active one is optically inactive
(B) There are five possible production ; three are optically inactive & two are optically active
(C*) There are five possible production ; two are optically inactive & three are optically active
(D) There are four possible production ; two are optically active & two are optically inactive

Q.6 Match the column-I with column-II, where column I indicates a pair compound and column II indicates
their relationship. Note that column-I may have more than one matching options in column-II.
[4]
Column-I Column-II

(A) & (P) Identical

(B) & (Q) Geometrical isomers

(C) & (R) Diastereoisomers

(D) & (S) Enantiomers

[Ans. (A): Q, R; (B) R; (C) P; (D): R]

[Sol. ]

Q.11 A basic nitrogeneous compound of molecular formula C4H5N gave C4H9N on complete hydrogenation.
When the hydrogenated product is subjected to Hoffman’s exhaustive methylation twice, 1,3-butadiene,
trimethylamine and 2 moles of water are obtained. Explain the structure of base and and show the
reaction sequence given above. [4]

[Sol. C4H5N : C4H9N :

(1) 3 2CH I (1) CH I

  
  3
   
( 2 ) Ag 2O aq. ( 2 ) Ag 2O aq. ]
(3 )  ( 3) 

Q.12 Give product of thermal decomposition of following compound. [3]


 Me 
 | 
CH CH  N  C(CH )  OH  
 3 2 | | 3 2
  ?
 Me CH 3 
 
[Ans. Gives (CH3)2C= CH2 + EtNMe2 (93%) and CH2=CH2 + t-BuNMe2(7%)]

Q.13 Amine (A)C6H15N on treatment with MeI & KOH gives (B) C8H20 N OH . This on heating produces
isobutene & amine (C) C4H11N. What is A? [3]

CH 3  C  CH 2
(1) MeI
KOH |
[Sol.    ]
( 2)  CH 3

Note: Students should solve the following questions of HALOGEN DERIVATIVES sheet
by 16th Sept. 2006
Exercise I – Q.1 to Q.38
Exercise II– Full
Exercise III– 1 to 29
Exercise IV(A)– Q.1 to Q.4, Q.6 to Q.9, Q.11, Q.13 & Q.14
Exercise IV(B)– Q.1 to Q.7
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.-18
Time: 40 Min. M. M. 41
Question No. 1 to 3
We have observed that SN1 reaction involve the formation of carbocations as intermediates. Further,
since carbocations are planar, they can be attacked by the nucleophile in the second (fast) step on either
side of the face. Thus if the starting compound is optically active, the product should be racemic mixture
with no optical activity. However, this is rarely observed in practice. Normally, the two enantiomer of the
product are not formed in equal amount; the enantiomer having inverted configuration with respect to the
reactant predominates and the second enantiomer of the product is present in less amount. Thus the
product contains a racemic modification and some amount of the enantiomer having inverted configuration.
On the basis of the above paragraph answer the following question:
Q.1 Which of the following statement(s) is/are true? [3]
(i) SN1 reaction of an optically active compound leads to racemic mixture having 50% original enantiomer
and 50% inverted enantiomer.
(ii) SN1 reaction is favoured by polar aprotic solvents.
(iii) In SN1 reaction the original enantiomer undergoes heterolytic clevage.
(iv) Vinyl chloride does not undergo nucleophilic substitution because of resonance stabilization.
(A) (i), (ii), (iii) & (iv) (B) (iii) only (C*) (iii) and (iv) (D) (ii), (iii) and (iv)

Q.2 Observe the following reaction: [3]

H O
2

  +
ethanol

(A) The product is exclusively I

(B) The product is a racemic modification having only I and II with I as the major component
(C*) The product is a mixture of four compounds.
(D) The product is optically inactive.

Q.3 Which of the following is true regarding the intermediate formed in the above reaction? [3]
(A*) A free carbocation is formed
(B) A carbanion is formed
(C) A penta coordinated transition state is formed
(D) The free carbocation formed undergoes rearrangement to form more stable intermediate.

Q.4 + H2O

18O will be in [3]

(A*) A (B) H2O (C) Both (D) None
Q.6 An isomer of it B gave compound C containing 62.8% chlorine with PCl5. C gives back B with aq.
KOH correct structure of B is: [3]
O
||
(A) CH2=CH–O–Me (B*) CH 3  C  CH 3 (C) (D) CH2 = CH–CH2–OH
Q.7 An isomer of A & B which gives two organic products with PCl5 is: [3]
O
||
(A*) CH2=CH–O–Me (B) CH 3  C  CH 3 (C) (D) CH2 = CH–CH2–OH

alc.base
Q.8 ClCH2CHCl2    A [3]
A is:
(A) CHCl = CHCl (B*) CH2=CCl2 (C) CHCH (D) ClCH2CHO

[Sol. HCl
 ClCH = CCl2 ]

Q.9 Which of the following will give ppt with aqueous AgNO3: [3]

(A*) Me3C–I (B) (C*) (Me3C)3C–I (D)

Q.10 Major product (B) in the following reaction sequence is [3]

NBS
 A NaI

 B
excess excess , 

(A) (B*) (C) (D)

Q.11 CCl4 does not give a precipitate with AgNO3 because: [3]
(A) it forms a complex with AgNO3 (B*) it does not ionise to give Cl– ions
(C) precipitate is soluble in CCl4 (D) AgNO3 does not give Ag+ ions.

Q.12 What will be the effect of increasing solvent polarity on the rate of following reactions [3]
 
(1) Me–Cl + Me3N  Me4 N Cl
(2) OH– + Me3S+  MeOH + Me2S
(3) Me3N + Me3S  Me4N + Me2S

Q.13 Arrange the following in order of: [4]

(a) Decreasing basic character : CH3 COO–, C6H5 O–, C 6H 5SO3
(b) Decreasing reactivity towards aq. KOH : C6H5CH2. CH2Br, C6H5CHBrCH3,
C6H5CH=CHBr
Q.11 Which of the following will not give carbylamine reaction [2]
(A) t-butyl amine (B) aniline (C) sec. butylamine (D*) N-methyl methanamine
[Sol. D is 2° amine]

Q.12 Correct order of rate of carbylamine reaction for following compounds is: [2]

(I) (II) (III)

(A) I > II > III (B*) II > I > III (C) II > III > I (D) III > I > II
[Sol. Based on order of nucleophilicity ]

Q.13 Rate of carbylamine reaction for Me–NH2 will be : [2]

(A) CHF3 > CHCl3 (B) CHCl3 = CHF3 (C) CHCl3  CHF3 (D*) CHF3 < CHCl3
   
[Sol. Order of electrophilicity C Cl 2 > C F2 ]

Q.14 Which intermediate is more stable in following pair. [4]

(A) and (B) and (C) and (D) and

Q.15(a) Cis-1,2-divinyl cyclobutane when heated upto 120°C gives cycloocta-1,5-diene. Shows a transition
state mechanism for this conversion.
(b) The trans isomer of the same compound do not give this product but when heated upto 200°C it gives
a monovinyl cycloalkene. Give structure of this product (mechanism not needed). [4]


[Sol. (a) 120
    or

(b) ]

Note: Students should solve the following questions of GOC sheet now.
Exercise III– Q.1 to Q.5, Q.9, Q.10, Q.12, Q.15, Q.16, Q.18, Q.20 to Q.22, Q.27,
Q.28, Q.30, Q.32, Q.34 to Q.36, Q.42, Q.50, Q.55 to Q.59, Q.61,
Q.67, Q.69, Q.70
 
Q.4 The product(s) of the reaction H
 is: [2]


(I) (II) (III) (IV)

(A) II, III and IV (B) II and IV (C) only I (D*) only IV

[Sol. Rimexpensi
  a  ]

Conc . H SO
2
Q.5    4  A. [2]


Product A is:

(A) (B) (C) (D*)

[Sol. Pinacol–Pinacolone rearrangement

RE


On the basis of -hydrogen H2O will removal ]

Question No. 6 to 13 (8 questions)

It is believed that chloroform and hydroxide ion react to produce an electron deficient intermediate
dichloro carbene : CCl2 (DCC)

—
OHH H2O + : :CCl2 + Cl

Treatment of phenol with DCC in basic medium introduces an aldehyde group, onto the aromatic ring.
This reaction is known as Reimmer Tiemenn reaction.


(i ) O H
   +
( ii ) :CCl 2 , ( iii ) H 

The Reimmer–Tiemenn reaction involves electrophilic substitution on highly reactive phenoxide ring. The
electrophilic reagent is dichloro carbene : CCl2

— 
+ :CCl2   O

H
  H
 
Q.5 H X [2]

X is:

(A*) (B)

(C) (D)

Q.6 Conversion : HCCH  CH3–CCD [4]

Ph–Br  Ph–D

Q.7 Suggest the mechansim of following reactions: [4]

CBr
(a) 4  (b) 

LiR

Q.8 Write the structure of more stable rearranged form of the following carbocations: [6]


(a) (b) (c) C H 2  CH 2  CH 2
|
CH 3  CH 2  O

(d) (e) (f)

Q.9 Predict the product of the following reaction and suggest the mechanism: [8]

 
(a) H A (b) H B
5C 


(c) H C (d) CHBr
3  D
 K  BuO 
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 14
Give major organic product in each case.
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 13
Max. Marks: 51(+3/–1) Time: 20 min
Q.1 In which of the following structures is the central carbon (C–3) not a chiral centre?

(A) (B) (C) (D*)

Q.2 Consider the following structures (A), (B), (C) and (D)

(A) (B) (C) (D)

Which of the following statements is not correct?
(A) B and C are identical (B) A and B are enantiomers
(C) A and C are enantiomers (D*) B and D are enantiomers
Q.3 What happens when an optically pure (+)–1–chloroethylbenzene (C6H5CHClCH3) is treated with
SbCl5 ?
(A) It remains unchanged (B) It produces (–)–1–chloroethylbenzene
(C) It forms 1–phenylethene as the sole product (D*) It racemizes

Q.4 The H–C–H bond angle in CH 3 : is
(A) 120° (B) 180° (C) 109°28' (D*) slightly less than 109°
Q.5 The correct order of stability of the following carbocations is

(A) (CH 3 ) 2 CH  > (CH 3 )3 C  > Ph 3C  >

(B*) > Ph 3C  > (CH 3 )3 C  > (CH 3 ) 2 CH 

(C) Ph 3C  > > (CH 3 ) 2 CH  > (CH 3 )3 C 

(D) (CH 3 )3 C  > > > Ph 3C 

Q.6 The correct order of stability of the following carbon radicals is
(A*) Ph3C· > (CH3)3C· > (CH3)2CH· > CH3CH2·
(B) CH3CH2· > Ph3C· > (CH3)3C· > (CH3)2CH·
(C) (CH3)3C· > (CH3)2CH· > CH3CH2· > Ph3C·
(D) (CH3)2CH· > (CH3)2CH· > (CH3)3C· > Ph3C·
Q.7 The correct order of stability of the following carbanions is
(A) > > >
(B) > > >
(C) > > >
(D*) > > >
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 12
TIME : 45 MIN. MAX. MARK : 41
Q.1 MeCH=CH–CH=C=CH–CH=CH2 [2]
Total number of geometrical isomers possible for above compounds are:
(A) 16 (B) 8 (C) 4 (D*) 2

Q.2 How many mono–chloro derivatives of 2–methoxy propane are possible? [2]
(A) 1 (B) 2 (C) 3 (D*) 4

Q.3 N-duetero-N-methylethanamine is optically inactive in basic or neutral medium, but it shows optical
activity in acedic medium. Explain. [3]

Q.4 An unknow compound weighing 4.2 gm is dissolved in enough carbon tetrachloride to make a total
volume of 250 c.c. The observed rotation of this solution is –2.25° in a 25 cm cell using the sodium D
line. Calculate specific rotation for this compound. [3]

Q.5 Identify the pairs of enantiomers and diastereomers from the following compounds I, II and III.
[3]

Q.6 What will be the effect on dipole moments of following compounds, when temperature is increased.
(a) cis-1,2-dichloro ethene (b) 1,2- dichloro ethane
Explain with suitable explanation in each case. [3]

Q.7 Which one of the following two pairs is more stable. [3]
(A) cis–1,2–dimethyl cyclohexane & Trans–1,2–dimethyl cyclohexane
I II
(B) cis–1,3–dimethyl cyclohexane & Trans–1,3–dimethyl cyclohexane
I II
[Sol. A–II & B–I ]

Q.8 Give RS configurations of following compounds. [3]

1) 2) 3)

[Sol. 1) 2S 3S 2) 2R 3S 3) R ]
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 11
TIME : 55 MIN. MAX. MARK : 61

Q.1 Select resolvable compounds. [4]

(i) C=C=CH2 (ii)

(iii) MeCHBrCH2Me (iv)

(v) MeCH 2 CHCH 2Me

|
OH

Q.2 Assign priority number to the following groups as per Cahn, Ingold, Prelog sequence rule [7]
(a) –CH2OH, –CH3, –CH2CH2OH, –H
(b) –Cl, –Br, –CH=CH2, –CH3
O
||
(c)  C  H –OH, –CH3, –CH2OH
(d) –CH(CH3)2, –CH2CH2Br, –Cl, –CH2CH2CH2Br

(e) –CH=CH2, –CH2CH3 , –CH3

CH 3 CH 3
| |
(f) –CH=CH2, –CCH  CH  CH 2 C— CH
| | | |
CH 3 CH 3 CH 3 CH 3
(g) –CH2CH2CH2I  CH  CH  CH 3  CH  CH 2 CH 3 –F
| |
Br Cl
[Sol. (a) 1 > 3 > 2 > 4 (b) 2 > 1 > 3 > 4 (c) 2 > 1 > 4 > 3 (d) 3 > 1 > 2 > 4
(e) 3 > 1 > 2 > 4 (f) 4 > 2 > 3 > 1 (g) 4 > 3 > 2 > 1 ]

Q.3 Indicate whether each of the following structure has the R configuration or the S-configuration.
[21]

(a) (b) (c)

(d) (e) (f)

Q.7 Write correct order of basicity.

(i)

(ii)

[Sol. (i) c > a > b (ii) b > c > a]

Q.8 Which will give most stable cation upon strong heating:
CH 2
||
(A) (B) (Ph)3C – Cl (C*) (D) CH
|
CH 2  Cl
Q.9 Correct order of carbonium ion stability is
   
(I) CH 2  CH 2  NH 2  CH 3  CH  NH 2 (II) CH 2  CH 2  NO  CH 3  CH  NO
(A) (I) (B) (II) (C*) both (D) none

Q.10 Which compound has greater electron density on oxygen atom?

O O
|| ||
NH  C  CH 3 or NH  C  CH 3
[Ans. 1]

Q.11 Arrange the following carbocations in decreasing orders of stability:

(a)

(b)

[Ans. (a) iv > iii > i > ii, (b) ii > i > iii > iv]

Q.12 Arrange the following in increasing order of stability.

(a) , , , ,

(regarding stability of free radical)

Q.24 Boiling point of nitromethane is 101 °C but boiling point of its functional isomer methyl nitrite is –12 °C.
Give reason for this. [3]
[Sol. Nitromethane can tautamerise into acenitromethane which can form intermolecular H–bond. Such thing
is not possible in case of methylnitrile. Also overall polarity of –NO2 group is much more then –O–N=O.

CH 3  O  N  O Not Possible ]

Q.25 Acetone in dilute aqueous solution is 100 % unhydrated. When acetone is dissolved in water enriched
with O18, recovered acetone contain O18. Explain. [3]

Q.26 Arrange the following in increasing order of b.p. & solubility in water. [4]
(i) C3H8, C2H5OH, (CH3)2O and CH2OH·CH2OH
(ii) 3-methylbutanol, n-Pentane, 2, 2-dimethylpropanol and n-pentanol

"Good better and best should never let your rest, until the Good becomes better and better becomes the best".
“Remember Improvement always begin with I”
Q.9 Which of the following reactions is highly favoured to the product–side and goes nearly to completion?
(A) PhOH + NaHCO3 —— PhONa + CO2 + H2O
(B) HCCH + NaOH —— HCCNa + H2O
ONa
|
(C) CH3COCH3 + NaOH —— CH 3C  CH 2 + H2O
(D*) [(CH3)2CH]2NH + CH3CH2CH2CH2Li ——[(CH3)2CH]2NLi + CH3CH2CH2CH3
Q.10 Which of the following bases would convert butanone to its enolate to the greatest extent?
O ONa
|| |
CH 3CH 2  C  CH 3 + BNa —— CH3CH 2  C  CH 2 + BH
Ketone base enolate
(A) C2H5ONa (B) CH3COONa (C*) (C6H5)3CNa (D) NaOH
Q.11 The correct order of increasing basicity is
(A) pyrrole < pyridine < Me3N < Et3N (B*) pyrrole <pyridine < Et3N < Me3N
(C) pyrrole < Et3N < Me3N < pyridine (D) Me3N < Et3N < pyridine < pyrrole
Q.12 Which of the following compounds is the strongest acid?

(A) C2H5OH (B) HCCH (C) (D*)

Q.13 Which of the following reactions does not occur in practice?

(A) Ph3CH + CH3(CH2)3Na —— Ph3CNa + CH3(CH2)2CH3

(B) + NaHCO3 —— CO2 + H2O

O O O ONa
|| || || |
(C) CH 3CCH 2 CCH 3 + EtoNa —— CH 3CCH  CCH 3 EtOH

(D*) + NaHCO3 —— + CO2 + H2O

Q.14 Which of the following is the strongest base?

(A) CH3COCH3 (B) CH3CH=CH2 (C) (D*)

Q.15 The correct order of decreasing basicity of the compounds

(F3C)3 N

I II III IV
is
(A) I > II > III > IV (B*) III > II > IV > I (C) II > IV > III > I (D) IV > III > II > I
Q.16 Among the following compounds, the one which will not show keto–enol tautomerism is

(A) (B*) (C) (D)

Q.14 Most volatile out of following is:– [2]

(A*) (B) (C) (D)

Q.15 Sulphanilic acid although has acidic as well as basic group, it is soluble in alkali but insoluble in mineral
acids. Explain. [2]

Q.16 Sulphanilic acid is insoluble in water as well as in organic solvents. Explain [2]

Sulphanilic acid

Q.17 Give the major product of following reaction. [3]

HCl


1equivalent

[Sol. ]

Q.18 Azulene and naphthalene both have same molecular formula C10H10. Napthalene which is a well known
moth repalent is in-soluble in aqueous acid, whereas azulene is soluble in aqueous acid. Explain
[3]

Azulene
[Sol. Azulene exist as zwittor ion. ]
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 8
TIME :60 MIN. MAX. MARK : 50
Q.1 What is the hybridisation of C— in —CH2 – CH = CH2 [2]
(A) sp3 (B*) sp2 (C) sp (D) unhybridised
Q.2 What is the shape of —CH3 [2]
(A) linear (B) Planar (C*) Pyramidal (D) All may be
Q.3 Given the following data [2]
CH2 = CH2 CH3CH2Cl CH2=CHCl
C–Cl bond length – 1.76 A 1.69 A
C=C bond length 0
1.34 A – 1.380A
C–C bond length – 1.540A
dipole moment 0 2.05 D 1.44 D
Explain all the comparison with reasons.

Q.4 Squaric acid is a diprotic acid with both protons being more acidic than acetic acid.

In the di-anion after the loss of both protons all of the C-C bonds are the same length as well as all of the
C-O bonds. Provide a explanation for these observations. [2]
Q.5 Arrange in the increasing order of basicity [2]

CH3 NH2

Ethane amidine
[Sol 3<4<5<2<1 ]
KOH
Q.6 PhCH2 – CH = CH2    PhCH = CH–CH3
heat
[3]
Provide a mechanism for the product formation.
Q.7 Arrange the order of increasing b.p. & give your reasons. [3]
(a) (CH2OH)2 (CH2OMe)2 CH2OH – CH2OMe
A B C
(b) Arrange the order of acidity of the following compounds
triphenyl methane diphenyl methane toluene
A B C
[Ans. A > B > C]
(c) Which is more basic & why ?

A B [Ans. A < B]
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 7
Q1. Draw the resonating structure of di-anion of squaric acid? Also explain why it is highly acidic.

Q2. Among the following reaction

E1, E2 are energy of  electron? Explain whether E1 > E2 or E2 > E1.

Q3.(a) (Tropone) on treatement with Base (OH–) followed by acidification yields Benzoic acid? Explain.

(b) Find out aromatic, anti-aromatic and non aromatic.

(percyclene) (Dipleiadiene) (Pyrene)

Q4(i) What is the acidity order of x, y and z

(A) x > y > z (B) x > z > y (C) y > z > x (D) z > y > x

(ii) Compound (A) has higher heat of hydrogentation than B

Q5. Calculate the resonance energy of N2O from the following data
Hf0 (N2O) = 82 kJ/mol
Bond Type Bond Energy
NN 946 kJ/mol
N=N 418 kJ/mol
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 6
Q1. o-nitrophenol is more volatile than m or p isomer. Explain.

Q2. The enol form of acetyl acetone is stable as compared to keto form. Explain with the help of hydrogen
bonding.

Q3. HCO2H, CH3CO2H acting as dimer & its apparent molecular weight is twice of actual molecular weight.
Explain.

Q4. Ninhydrin forms very stable hydrate. Explain.

Q5. Which of the following carbonyl system forms H–bonding?

(a) HCHO (b) CH3CHO (c) Me3CHO (d) CH3COCH3 (e)

Q6. Which of the following system forms intra/inter molecular hydrogen bonding/no hydrogen bonding.
(a) salicylic acid (b) quinol (c) catechol (d) milk of rose (e) NH3
(f) PH3 (g) R3N (h) CHCl3 (i) ChCl3 + CH3COCH3

(j) Ether water system (k) (l)

(m) conjugate base of Phthalic Acid.

Q7. Explain Why? Although boron trifluoride adds on trimethylamine, it does not add on triphenylamine.

Q8. Acetone in dilute aqueous solution is 100 % unhydrated. When acetone is dissolved in water enriched
with O18, recovered acetone contain O18. Explain.

Q9. The order of viscosity of the liquids:

CH 3
|
(a) CH3– CH2– CH2– CH2– CH2– CH3 (b) CH 3  CH 2  CH  CH 2  CH 3

CH 3
|
(c) CH 3  CH  CH  CH 3
|
CH 3
(A) will be the same (B*) a > b > c (C) a < b < c (D) a > b = c
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 5
Q1. Which of the following is aromatic species?

(A) (B) (C) (D*) All

Q2. Which of the following is anti-aromatic species?

(A) (B) (C) (D*)

Q3. Which of the following is non-aromatic?

(A) (B*) (C) (D)

Q4. Which of the following is non-aromatic?

(A) (B) (C*) (D)

Q5. Which is the most aromatic in character?

(A) (B*)

(C) (D) All having same aromatic character

Q6. Which has the most aromatic nature?

(A*) (B)

(C) (D) All having same aromatic character

Q7. Which of the following annulene system acting as aromatic species?

(A) 8 annulene (B) 4 annulenes (C*) dehydro-14-annulene (D) None
Q8. Tropolone when reacts with HCl it forms very stable product because
(A) product having 6 membered ring. (B) product having very high covalent character
Q11. Diazomethane is best represented as a resonance hybrid from linear resonating structures shown as
below

  

Which of the following statement is correct

(A) II indicates CH2N2 can act as electrophile (B) III indicates CH2N2 can acts as nucleophile
(C) IV indicates CH2N2 can act as 1, 3 dipole (D*) all are correct
 
Q12. Ph N 2 is more stable than R N 2 because

(A*) in Ph N 2 , +ve charge undergoing delocalisation in the ring.
(B) Ph having –I effect whereas R having +I effect.
(C) in Ph group carbon is more electron defficient w.r.t. carbon in R group.
(D) all are correct

Q13. The heat of hydrogenation of cyclo octene is –23 K cals mole–1 the heat of hydrogenation of cyclo
octatetraene is –98 K cals mole–1. Cyclo octatetraene is thus
(A) very stable having aromatic character.
(B) it is stabilised like benzene when compared with relevant hypothetical cyclic polyene.
(C) during hydrogenation it looses resonance energy.
(D*) it is non aromatic & highly destabilised w.r.t. hypothetical cyclic polyene.

Q14. Explain why methyl thio alcohol has less pH as compared to methanol under similar physical condition
when dissolved in water.

Q15. Arrange in increasing order of Ka value

(a) CH3CN, (b) CH3Cl (c) CH3NO2
Arrange in decreasing order of pKb value
(a)CH3NH 2 (b) NH3 (c) CH3CONH2

Q16. Explain the following facts:

 
(a) R – C = O is less stable than R–C  O
(b) Aromatic amines are weaker base than aliphatic amines.
(c) Metal hydride are stronger base than metal hydroxide.

Q17. Arrange in the increasing order of pKa values

CH3NH2

Ethane amidine

Q18. What is the order of basicity of the following compounds?

PhNH2 PhNHMe PhNMe2 p–MeC6H4 NH 2
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 3
Q1. The weakest acid among the following
(A) CH3COOH (B) CH3CO2OH (C) Cl-CH2-COOH (D) CH3-CH2-COOH
Q2. The strongest acid among the following is

(A) (B) (C) (D)

Q3. Maximum basicity is express by

(A) (B) (C) (D)

Q4. Among , , CH3-CH2-OH, CH3-OH which solution in water express maximum PH value

(A) OH– (B) CH3– (C) CH3-CH2-OH (D) CH3-OH

Q5. Which has maximum pKa value
(A) MeO–CH2–COOH (B) CH3-CH2-COOH
(C) Cl-CH2-COOH (D) HO-CH2-COOH
Q6. Arrange is increasing of pKa value of the following
Cl
\
(a) F-CH2-COOH (b) Cl-CH2-COOH (c) CH  COOH (d) CCl3-COOH
/
Cl
(e) Br-CH2-COOH (f) CH3-COOH; correct answer is
(A) d<c<a<b<e<f (B) d<a<b<f<c<e (C) a<b<c<d<e<f (D) b<a<f<c<e<d
Q7. Arrange in increasing order of pKa value
Cl
|
(a) CH3-CH2-COOH (b) CH 3  CH 2  CH  COOH

(c) Cl-CH2-CH2-CH2-COOH (d) CH 3  CH  CH 2  COOH

|
Cl
correct answer is
(A) b<a<c<d (B) b<d<c<a (C) a<b<c<d (D) a<b<c<d
Q8. Arrange in increasing pKb
(a) HC  C  CH 2  NH2 (b) CH2=CH-CH2-NH2 (c) CH3-CH2-CH2-NH2
(A) c<b<a (B) a<b<c (C) b<c<a (D) b<a<c

Q9. Basic strength of , , will be in order

(A) I < II < III (B) II < III < I (C) III < II < I (D) III < I < II
Q10. Arrange in increasing pKa
(a) O2N-CH2-COOH (b) HOOC-CH2-COOH (c) CH3-CH2-COOH
(A) a < b< c (B) c < b < a (C) b < a < c (D) b < c < a