ORGANIC CHEMISTRY

Daily Practice Problems

CLASS : XII (ALL) DPP. NO.- 22
Q.1 In the given reaction:
C6H5– CH = C + HBr Peroxide
  [X]
[X] will be
Br Br
| |
(A) C 6 H 5  CH  CH (B) C 6 H 5  CH  C
|
Br

(C) C 6 H 5  CH 2  C (D) C6H5– CH = C

|
Br
Q.2 Arrange the following carbocations in the increasing order of their stability.

(I) (II) (III)

(A*) I > II > III (B) I > II = III (C) I > III > II (D) III > I > II
[Sol. (I) Two benzenoid RS & Two H(II) Two benzenoid RS & but zero H
(III) Only one benzenoid RS zero H ]
Q.3 Which statement about the following equilibrium is/are true?
 
Ph3C–H + MeO K

Ph3C K  + MeOH
(I) The reaction favours the product formation.
(II) Ph3CK is the dominant anionic species in this reaction.
(III) Methanol is the weaker acid in this reaction.
(IV) The reaction favours the reactant formation.
(A) I & II (B) I, II & III (C*) IV only (D) III & IV
[Sol. Reaction moves towards weaker acid & base ]
Q.4 Which one of following carbonyl compound when treated with dilute acid forms the more stable
carbocation?
O O
|| ||
(A) CH 3  C  CH 3 (B) (C*) (D) C 6 H 5  C  C6 H 5

[Sol. C will form aromatic cation by attack of Hon carbonyl oxygen.]

Q.5 Correct order of heat of combustion is:
(p) 1,3-Pentadiene (q) 1,3-Butadiene
(r) 2,3-Dimethyl-1, 3-butadiene (s) Propadiene
(A) s > q > p > r (B) s > r > q > p (C*) r > p > q > s (D) s > r > p > q
[Sol. More the no. of C & H in the compound more will be heat of combustion]
Q.6 The most stable resonating structure of following compound is

(A) (B)

(C) (D*)

[Sol. D is octet complete R.S. with –ve on more electronegative atom "O". ]
Q.7 It required 0.7 g of a hydrocarbon (A) to react completely with Br2 (2.0 g). On treatment of (A) with
HBr it yielded monobromo alkane (B). The same compound (B) was obtained when (A) was treated
with HBr in presence of peroxide. Write down the structure formulae of (A) and (B) and explain the
reactions involved.
Q.8 Complete the following:
CH3 – CH = CH2 + CHCl3 Peroxide 
  (A) Ag
/  (B)

( i ) CH 3  Li ( excess ) ( i ) SOCl
(E)      (D)  2 (C)
( ii ) H  ( ii ) CH 2 N 2
( iii ) Ag 2O / HOH

Q.9 Write the most probable product of the following reaction

CH ONa
3 Product [Ans. ]

Q.10 Purpose mechanism for following conversion.

( i ) CH MgBr
 3 
( ii ) H 2O

Q.11 Complete.

KHSO KHSO
(i) 4  A
HO  CH 2  CH (OH)  CH 2  OH   (ii) 4  B
 
 
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 23
Time : 30 Min. Max. Marks: 27


Q.1 
 Which of the following product cannot be obtained by this reaction. [2]
Ei

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

Q.2 CH2 = C = O (

i ) Br2
 C4H8O [2]
(ii ) CH 3MgBr
( 2 equi )

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

Br
Q.3alkene 2  HOOC  CH  CH  COOH (X) [2]
CCl 4 | |
Br Br

Br
2  HOOC  CH  CH  COOH (Y)
CCl 4 | |
Br Br
The correct statement with respect to above reactions are
(A*) The reaction is stereospecific
(B*) (X) is erythro and (Y) is threo isomer
(C) (X) is threo and (Y) is erythro isomer
(D) each gives mixture of (X) and (Y)

( i ) Mg / ether
Q.4alkene Which is B in the sequence HBr
 A    
B [2]
(ii ) CO 2 / H 3 O

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

Q.5 Identify A, B and C and give their structures. [3]

Q.6alkene Give mechanism for given reaction: [4]

H  / HOH
 

-Terpeniol

[Ans. H  HOH / H  ]
  

Q.7 Draw the structures of stable configuration obtained after acidic hydration of the following unsaturated
compounds: (exclude rearranged products) [4]

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

[Ans. (I) (II) (III) (IV) ]

Q.8 Formulate mechanisms for the following transformations. [4]

CH N
2
2 

[Sol.

]
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 24
Time : 45 Min. Max. Marks : 42
CH 3
| conc.H SO
Q.1elimination CH 3CH 2 CH 2 CH 2 CCH 2 OH  24  Major product is: [2]

|
CH 3

CH 2
||
(A*) CH3CH2CH2CH2CH= (B) CH 3CH 2CH 2CH 2C
|
CH 2CH 3

(C) CH 3CH 2CH 2CH 2C  (D) CH 3CH 2 CH 2CH  C  CH 2CH 3

| |
CH 3 CH 3

Q.2 Me2CDOH is oxidised by H2CrO4/aq. acetone at about 1/7th the rate of either Me2CH(OH) or (CD3)2
CHOH – explain. [2]

[Sol. Because of Bond Energy of ]

LAH
Q.3  A PBr3 Alcoholic KOH
dry ether
 B     C

What are A to C ? [3]

[Sol. (A) (B) (C) ]

Q.4alkene Assign A to D in the given reaction sequence [4]

( i ) CH I ( excess) ( i ) CH I ( excess)
 3   A  3   B
( ii ) AgOH,  ( ii ) AgOH, 

[Sol. A= B = MeOH ]

Q.5 How will you convert cyclohexane into benzene in four steps. [3]

Br
[Sol. 2  alc
KOH NBS
 alc
KOH ]
h excess
Q.6 PhOCH2Cl + Ph3P + tBuO—K+  A (C25H21P) [3]
A + ethyl methyl ketone  Ph3P = O + B (C11H14O)
B + dilute aqueous acid  C (C5H10O)
What are A to C?
O
||
[Sol. A = Ph3P = CHOPh B= C = C 2 H 5  CH  C  H ]
|
CH 3
Q.7 Complete the following reactions.

(a) + PPh3  A + B
(b) ClCH2COMe Ph 3P
 EtOH
 A EtONa   B [4]
[Sol. (a) A = CH2 = CHMe + Ph3P = O = B


(b) A = (Ph 3 P CH 2 COMe)Cl
B = CHC–Me ]

Q.8 Complete the following reactions.

EtOLi
(i) PhCH=CHCH2PPh3+Cl— A PhCHO
  B + C

(ii) Ph3P + (i) ClCH2COMe  D Na CO 3

2 E PhCHO
  F.. [6]
[Sol. (i) A = PhCH = CHCH2= PPh3
B = Ph–CH=CH–CH=CH–Ph
C = Ph3PO

(ii) D = ( Ph3 P CH 2COMe)Cl -
E = Ph3P = CHCOMe
F = Ph–CH=CHCOMe ]

Q.9 Give structure of A to J. [9]

reduction
  A (C9H17ON, an alcohol)

A + heat  B (C9H15N)
B + CH3I + Ag2O  C (C10H19ON)
C + heat  D (C10H17N)
D + CH3I + Ag2O  E (C11H21ON)
E + heat  F (C8H10)
F + Br2  G (C8H10Br2) [Thermodynamically controlled pot]
G + Me2NH  H (C12H22N2)
H + MeI + Ag2O  I (C14H30O2N2)
I + heat  J (C8H8)

[Sol. (A) (B) (C) (D)

 (E) (F) (G) (H)

(I) ]

Q.10 (a) Complete the following reactions: [6]

 
 BuO K
(i) Ph3P + CHCl3 t   A
O
EtO Na
||  
Ph 3P
(ii) PhCO(CH2)4Br   B   Ph  C  (CH 2 )3  CH  PPh 3  C + D.
EtOH

(b) Rate law for substitution reaction of 2-bromobutnae with OH in 75% ethanol & 25% water at
30°C is rate = 3.20 × 10–5 (2-bromobutane) (OH–) + 1.5 × 10–6 (2-bromobutane) what
percent of reaction take place by SN2 when [OH–] = 1.00 m.

O
|| 

[Sol. (a) A = Ph3P = CCl2 , B = Ph  C  (CH )
2 4  P Ph3 Br ,C= , D = Ph3P =O

S
N2
(b) % by S N 2 = × 100
S S
N2 N1

3.20  105[2  bromobutane][1.00]  100

=
3.20  10 5[2  bromobutane][1.00]  1.5 10  6 [2  Bromobutane]

3.20 10 5
= 5 × 100 = 96% ]
3.20 10  0.15 10 5
 ORGANIC CHEMISTRY
Daily Practice Problems
CLASS : XII (ALL) DPP. NO.- 25
Time : 35 Min. Max. Marks: 31
Q.1 Which alkyl halide would you expect to react more rapidly by an SN2 mechanism? [5]
(a) CH3CH2CH2Br or (CH3)2CHBr

(b) CH3CH2CH2CH2Cl or CH3CH2CH2CH2I

(c) (CH3)2CHCH2Cl or CH3CH2CH2CH2Cl

(d) (CH3)2CHCH2CH2Cl or CH3CH2CH(CH3)CH2Cl

(e) C6H5Br or CH3CH2CH2CH2CH2CH2Cl

[Ans. a1, b2, c2, d1, e2]

Q.2 Which SN2 reaction of each pair would you expect to take place more rapidly in a protic solvent?
[4]
(a) (1) –
CH3CH2CH2Cl + CH3CH2O — CH3CH2CH2OCH2CH3 + Cl –

OR
(2) CH3CH2CH2Cl + CH3CH2OH — CH3CH2CH2OCH2CH3 + HCl

(b) (1) CH3CH2CH2Cl + CH3CH2O– — CH3CH2CH2OCH2CH3 + Cl–

OR
(2) CH3CH2CH2Cl + CH3CH2S — CH3CH2CH2SCH2CH3 + Cl–
–

(c) (1) CH3CH2CH2Br + (C6H5)3N — CH3CH2CH2N(C6H5)3+ + Br–

OR
(2) CH3CH2CH2Br + (C6H5)3P— CH3CH2CH2P(C6H5)3+ + Br–

(d) (1) CH3CH2CH2Br(1.0M) + CH3O–(1.0M) — CH3CH2CH2OCH3 + Br–

OR
(2) CH3CH2CH2Br(1.0M) + CH3O–(2.0M) — CH3CH2CH2OCH3 + Br–
[Ans. a1, b2, c2, d2]

Q.3 Which SN1 reaction of each pair would you expect to take place more rapidly? Explain your answer.
[5]
(a) (1) (CH3)3CCl + H2O — (CH3)3COH + HCl
OR
(2) (CH3)3CBr + H2O — (CH3)3COH + HBr

(b) (1) (CH3)3CCl + H2O — (CH3)3COH + HCl

OR
(2) (CH3)3CCl + CH3CH2OH — (CH3)3COCH2CH3 + HCl

(c) (1) (CH3)3CCl(1.0M) + CH3CH2O–(1.0M) EtOH

 (CH3)3COCH2CH3 + Cl
–

OR
(2) (CH3)3CCl(2.0M) + CH3CH2O–(1.0M) EtOH
 (CH3)3COCH2CH3 + Cl
–

(d) (1) (CH3)3CCl(1.0M) + CH3CH2O–(1.0M) EtOH

 (CH3)3COCH2CH3 + Cl
–
 OR
(2) (CH3)3CCl(1.0M) + CH3CH2O–(2.0M) EtOH
 (CH3)3COCH2CH3 + Cl
–

(e) (1) (CH3)3CCl + H2O — (CH3)3COH + HCl

OR
(2) C6H5Cl + H2O — C6H5OH + HCl
[Ans. a2, b1, c2, d same, e1]

Q.4 Discuss the type of isomerism exhibited by the following pairs: [4] (a)

and

(b) and

(c) and

(d) and

[Ans. (a) Both are similar structures, (b) They are positional isomers, (c) They are enantiomers, (d) They are
constitutional isomers]

Q.5 Give the following equations and comment where necessary. [4]
 2 RMgX
(i) ClCH2CO2Et    ?
( i ) Et O , ( ii ) H 
(ii) nC H MgBr
4 9
i ) Et 2O, ( ii ) H 
+ ? (    C7H15OH
n
2

Q.6 Give product(s) in each of the following reactions [4]

(a) CH3 – CH – CH2 – CH2– CH3 Br / hv

2  (A)
|
CH 3

( C H CO ) O
(b) + NBS 6 5  2 (B)

hv
(c) CH3 – CH2 – CH = CH2 + (CH3)3 – C – O – Cl  (C) + (D)
CH 3
|
CH 3 C O Cl / 
|
CH 3
(d) C6H5 – CH2 – CH2 – CH3      (E)
 Br
|
[Sol.(a)A: CH 3  C  CH 2CH 2CH 3 (b) B:
|
CH 3

(c) C: CH 3  CH  CH  CH 2 D: CH 3  CH  CH  CH 2 Cl
|
Cl
(d) E:

Q.7 A concentrated aqueous solution of HBr reacts with EtOH to give EtBr but a concentrated aquous
solution of NaBr does not – explain. [2]
[Sol. Poor LG -OH cannot directly substituted by ]

Q.8 Oxirane (epoxy ethane) when reacts with DMSO  hydroxy carbonyl compound is formed as product
– explain with mechanism. [3]

[Sol.


O  C  CH 2  OH + (CH3)2S]
|
H

Note:— Consider the following list provided below in place of the list of questions given to you at the
end of DPP - 22 (dt. 21-22/08/06) of HALOGEN DERIVATIVES sheet. Solve it by
16th Sept. 2006

Exercise I(A) – Q.1 to Q.38

Exercise I(B)– Full

Exercise II– 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