Alkyl Halide DPP (With Solution) and Sheet

CONTENT
S.No Pages
0. Answer Key 04
1. DPP-1 05 – 6
2. DPP-2 07 – 8
3. DPP-3 09 – 10
4. DPP-4 11 – 13
5. DPP-5 14 – 15
6. DPP-6 16 – 18
7. DPP-7 19 – 20
8. DPP-8 21 – 23
9. DPP-9 24 – 26
10. DPP-10 27 – 31
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Answer Key
DPP-1
1. C 2. C 3. A 4. B 5. B 6. B 7. C
8. A 9. A 10. C
DPP-2
1. A 2. C 3. D 4. C 5. BCD 6. ABD 7. AB
8. A 9. D 10. A
DPP-3
1. C 2. C 3. A 4. C 5. B 6. B 7. C
8. A 9. C 10. D
DPP-4
1. B 2. C 3. A or B 4. D 5. ABD 6. B
DPP-5
1. B 2. A 3. B 4. (A) 5. D 6. B 7. C
DPP-6
1. B 2. A 3. B 4. B 5. C 6. B 7. C
8. A 9. C 10. C
DPP-7
1. C 2. A 3. B 4. B 5. B 6. A 7. B
8. B 9. A
DPP-8
1. C 2. A 3. A 4. D 5. B 6. D 7. D
8. B 9. A
DPP-9
1. B 2. D 3. C 4. B 5. ABCD 6. AC 7. AC
8. AD 9. 2 10. 3
DPP-10
1. A 2. B 3. A 4. B 5. A-PR ; B-QR ; C-Q ; D –T
6. C 7. 4 8. 3 9. 6
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
Class : XII Time : 30 min. DPP # 1
1. C
CH2 Cl CH2 SH

KSH
(SN2)
Br Br
No. SN2 here due to

double bond character
2. C
If equal amounts of retention and inversion occur, then for every event that results in the loss of two units of
optical activity, we have another event that results in the loss of no optical activity; on average, K°/KS=1.
3. A
C2H4Cl2 may be
O
CH2 Cl CH2 CN  CH2 COOH CH2 C
(A) KCN H3O 
O Succinic anhydride
CH2 Cl CH2 CN CH2 COOH -H2O CH2 C
O
Cl CH COOH

KCN H3O 
(B) CH3 HC CH3 CH CH3 HC CH3 CH2 COOH
-CO 2
Cl CH COOH
4. B
 2
NaNH2 CH3 Br (SN ) better
CH C C CH3
AB due to less sterric ++ +
Hg /H
H 2O
OH
C CH3
Tauto
O
C CH3
5. B
O Cl Cl
Cl Cl
x PCl 5 yNaNH2 CH3I

x=2 y=3
O Cl
Cl
6. B
(i) 2 moles of HI used (ii) 1 mole of H l used
(iii) 2 moles HI (iv) 3 moles of HI used
(v) 2 moles HI used (vi) 1 mole HI Total 11 moles of Hl are used.
7. C
Br  is better leaving group then Cl and NaI/acetone will favour SN2 reaction due to which product will be
inverted.
8. A
I I I
NBS KSH
CH3 CH2Br CH2SH

9. A
OH 2° OH OH
(1) NaNH2
(1 mole) (2) CH3I
(1 mole) (1 mole)
CH2OH CH2O CH2 O
OH OH OH
3° 1° CH3
Cold KMnO 4
CH2OH
OH
(B)
10. C
A,B are
O
O
(A) (B)
(Positional isomers)
ORGANIC CHEMISTRY
1. A
KI
CH3CH2CH2Cl 
Acetone
 SN2
O
CH3 C CH2 Cl  Ki
 SN2
Acetone
O
2
Rate of SN = CH3 C CH2 Cl > CH3CH2CH2Cl
2. C
Since the reaction is reversible k°/Ks =1
3. D
No SN2 due to steric hindrance

Br
Cl
No SN2 due to bredt’s rule
No SN2 due to double bond character with leaving group(-I)
4. C
Nucleophilicity runs parallel to basicity in this question.
More the negative charge unstable, more will be the nucleophilicity.
5. BCD
(A) I- > Br- > Cl- > F- Due to salvation in polar protic solvent
(B) F- > Cl- > Br- > I- Nucleophilicity in polar-aprotic solvent
- - - -
(C) I > Br > Cl > F Leaving group order
(D) Leaving group ability is same for both SN1 & SN2
6. ABD
O O O
(A) (B) (C) R C OCH (D)

3
O
7. AB
(C) Bridge head carbon cannot undergo SN2 reaction.
(D) R and S both are obtained in product. That means it followed SN1 path.
8. A
9. D
10. A
CH CH C CH2CH3
C C C
1. NaNH2 2. CH3 CH2 I

2. (2 eq) (SN2)
   
OH O Na O Na
Scheme-I
SN2 (3) CH3-I
C CH2CH3
C
CH CH2CH3
H2/Pd-BaSO 4
CH OCH3
(Syn-addition)
(cis) : (x)
OCH3
ORGANIC CHEMISTRY
1. C
CH3 CH3 CH3 CH3
H2 O
SN 1

Cl
CH3 CH3
 molecular plane of symmetry and vertical plane of symmetry present in given carbocation

2. C
Cl Cl Cl
Cl 2 * + * + * +
hv
Cl Cl Cl Cl Cl Cl
Thus, total 7 dichloro products are possible.
3. A
CH3  H3C CH3
conc. H
H3C O CH3 
H3C CH3
(tert-butyl iodide)
+ CH3 OH
(Methanol)
4. C
Ans (C) 80% H2O + 20% Acetone
More % of H2O increase the inversion (SN2) product during T.S. of carbocation formation.
100% H2O = 80% racemisation
80% H2O + 20% Acetone = 98% racemisation
5. B

HCl Cl
Cl

CH2
CH3 CH3

(no C rearrangement)
Addition of HCl according to markornikov rule.
6. B
Br CH3 CH2 Br
(No SN1 reaction)

(Give SN1 reaction)
7. C
Cl
(R) 
H2O
SN1 
Ph Ph (R) Ph
(R)
OH
OH
*
2 * 2
Ph (R) Ph
Total = 4
8. A
Br2 CH 3OH(aq.) Br2 CH 3OH(aq.)

hv Fe
Br
CH3OH
SN1 OCH3 + HBr
CH3OH(aq.)
No reaction
Br
9. C
Rate of SN1  stability of carbocation
CH3 O
   
CH3 CH CH3 C CH2 CH3 O CH2

Highly unstable Highly stable due to
O 
+M of O CH3
due to -I.E. of C 
Stability II > I > II, Rate of SN1 III > I > II.
10. D
Rate of SN1  [Nu-]º [R-Br]1
SN1 reaction does not affect by concentration of Nu-
ORGANIC CHEMISTRY
1. B
CN
CN CN
 SN2 Br HC
H2C EtO
CH Br Br CN
CN CN
CN CN
CN 
SN2 EtO
C
(intramolecular) Br CN
2. C
MeO I
MeO OMe
Me 
'NGP' Me AcO
 Me
Retention
OTs
OAc
II
Me
Me
Enantiomer
Me
Me
OAc
Inversion
Me
MeO
(II)
(Racemic mixture)
3. A or B
4. D
OH
OH (fixed) O
OH
H3C
Br
H3C
CH3 Br
Br
(Proper backside orientation)
O
SN2
O
Br
(A)
OH
Br
(B)
OH
OH
(C)
Br
Will not give anti-orientation for attack in anti-bonding molecular orbital.
5. ABD
(A) Hydrolysis of ether is not possible in basic medium.
(B) Deactivating NO2 group decrease the rate of hydrolysis.
Ph Ph Ph

H  H2O
(C) Ph C O Ph Ph + PhOH OH
SN1
Ph Ph Ph Ph
(D) Activating group increase the rate of hydrolysis by stable carbocation with resonance.
6. B
H
con. HI 
(P) CH3 O CH3 O CH3OH +
SN1
 
I
OH Cl
SOCl 2
(Q)
SN1
OH Cl
PCl 5
(R)
SN2
OH OH OH
NBS Br
(S)
 
ORGANIC CHEMISTRY
1. B
Since, leaving group is same, thus, we will check stability of melsenheimer complex (intermediate)
Cl OH Cl OH Cl OH strong Cl OH Cl OH
NO 2 M NO 2 O 2N NO 2
< < <
NO 2 NO 2
(i) (ii) (iii) (iv)

Thus, more the number of –NO2 groups, more stable will be the intermediate.
2. A
H
N O
(Activated
site note hindered)
3. B
In SN Ar reaction, nucleophile attackes at the O, P position of NO2 group.
NO 2 NO 2 NO 2
SNAr
F F F
HO Br
Br OH
4. (A)
Br
NO2
More no. of –NO2 group at O/P, more rate of SNAr.
NO2
5. D
Rate of reaction :
  
F Cl Br






> > >
For halogens : -> + M

6. B
(P) Substitution takes place in only compound (1). In compound (4), HBr will be eliminated hence elimination
reaction, not substitution. Hence compound (1).
(Q) Williamson ether synthesis  substitution can NOT take place on benzene hence compound (3).
(R) Aq ethanol will substitute Br- with EtO- and H+ ions released in the solution turning the solution acidic in
compound (4) hence compound (4).
(S) In compound (3), after cleavage, positive charge will be on benzene ring which is highly unstable hence
compound (2).
7. C
Cl O CH3

(P) NaOCH3
SN2
NO 2 NO 2
Br Br
(By biomolecular nucleophilic substitution reaction (SN2))
NO 2  NO 2
(Q) KOH

F HO
Cl Cl
(By nuclophilic aromatic or SN-r substitution)
Cl Cl
HNO3
(R) 
NO2
CH3 CH3
(Electrophilic aromatic substitution)
O CH3 OH

H3O
(S) + CH OH
SN1
CH3 CH3
(By hydrolysis of ether)
ORGANIC CHEMISTRY
1. B
Anti hydrogen results into antiperiplanar elimination of the following sulfonate ester of methol.
O H H
O
Heat
N S O
H O H H
2. A

EtO
(P) + +
Br EtOH (trans)
(P) major

t-BuO
Br 
t-BuOH (Q)
(hindered)
(P, Q are positional isomers)
3. B
Rate constant is highest for (ii) because aromatic product formed.
Br
alc. KOH
Aromatic
O  O
4. B
Cl
 Tautomerise 
t-but O t-but O
t-but OH AB

O O OH O
5. C
OH Cl
SOCl 2
A
A

E2 EtO
EtOH
+ +
(2) (1) (2)

5 Products
6. B
Br
NaNH2
+
Diastereomers
7. C
E2 elimination
Cl
8. A
Alc. KOH favours E2 reaction
Order = 3° > 2° > 1°
(i) (ii) (iii)
9. C
Option (C) cannot used to synthesis propyne.

(A) CH3 CH CH t-butO CH3 C CH
Br

(B) CH CNa + CH3 I CH C CH3
  
(C) HC CH + 2CH3Na NaC C Na + 2CH4
(1) NaNH 2 (excess)
(D) CH3 CH CH CH3 C CH

(2) H
Br Br
10. C
-
CH3 CH CH3 will undergo fastest E2 reaction due to relatively stable anion and good leaving group I .
I
ORGANIC CHEMISTRY
1. C
 H

 * *
-H HBr
 Br
Two chiral center
2. A
conc. H2SO 4
Me
 Shift
 
OH

HSO 4 H
3. B
H Br 
CH3ONa
+
E2
4. B
- *
H shift -H
OH + H2SO4 OH OH O
 
CH2 CH3
5. B
CH3
CH3
N
N
OH 

HEME
HCl 2-times


6. A
CH3

TsCl EtO /EtOH
+

OH OTs
(B) (C)
KSH
DMSO
SH
(D)
7. B
Rearrangement occurs to produce a more stable carbocation.
8. B
H O
Cl
NaOEt O 3, Zn CHO
H E2 H2O
(X) (Y) or Final product
9. A

H

OH
Enantiomers
“By dehydration of alcohol”
ORGANIC CHEMISTRY
1. C
Br
alc. KOH
By E2 reaction + +
G.I.  G.I.  G.I. 

Total products = 4.
2. A
3. A
OH


 
H Ring -H
Dehydration -H 2O Expansion 
A O 3/H2O 2
O O
HO C (CH2 )4 C OH
Dicarboxylic acid
4. D
[1 to 3 Solution]
OH OH
Cold HIO 4
CH CH2 CH CH2 CH O + CH2 = O
KMnO 4
(B) (C)
(A)
H Br

CH CH3

1,2 Me shift

+ Br
alc. KOH O3
O
By E2 Zn/H2O
Br
D E F
OH
Br2 H2O
CH CH2 CH CH2 CH CH2
+
Br Br
5. B
6. D
7. D
+ N
N

+ CH2=CH2
OH (by E2)
8. B

Et O
Anti-elimination
(By E2)
Br
9. A
Br 
NaNH2
(A) E2
Br
t-Butoxide
(B) E2 (Strong hindered base)
H3C 
(C) CH3 (E1)

O N
F
Et O
(D)  (Poor leaving group)
(E 2)
ORGANIC CHEMISTRY
1. B
On E2 elimination, Product are :
CH3
(1) C C CH2 hiral with fixed configuration (E and Z)

CH3 C CH3
CH3 C
CH3
(2) C C CH Chiral with fixed configuration (E and Z)

CH3 CH CH3
CH3
2. D
Hoffman exhaustive methylation & elimination

NH2 N
(1) CH 3 I (2) Ag 2O
(excess) (3) 
3. C
OH
-
 1, 2H  
shift

+
3 possible structure
4. B

OH OH
N
 N
+ H

N
H
5. ABCD
O OH
C
O 3/Zn Ni/H2
-HCHO
H3PO 4
 

1,2H ring
expansion

-H
+ +
(B) (A)
(C) (D)
6. AC
HO OH OH OTs O

TsCl/Py
 C (X)
1,2 CH3
H H H
HO OH OH

H O
 
H /  H /
 C CH3 (Y)
1,2 H
H H
12 H OH O

Hg /H tauto
C C CH3 CH2 C CH3
H OH O
H.B.O. tauto
C C CH3 CH2 C CH3
7. AC
OCH3 O O Br O Br O
NaOH/  Br2
Ph Ph Ph Ph
CCl 4
Br Br
Br
Base
(P)
COOH
Br
Base
(Q)
COOH
8.
AD
Br
Base
E2
COOH COOH
Br
Base
E2
COOH COOH
9. 2
Br
Br2 Et O NBS
hv E2-Elimination
Br E2 Alc. KOH
H2
Ni
10. 3
H Alc. KOH
+ +
Br
CH3 CH3 CH2
H
ORGANIC CHEMISTRY
1. A
Solvolysis  E1
Ph CH2 CH CH3 Ph CH2 CH CH3 Ph CH2 CH CH3 + Ph CH CH CH3
 SN1 (cis + trans)
Cl 1,2 H
(trans major)
Shift *
Ph CH2 CH CH3
 Cl
Ph CH CH CH3 Ph CH CH2 CH3
(Racemix mixture)
SN1
*
Ph CH CH2 CH3
OH
(Racemic mixture)
Thus, total (SN1 + E1) products = 4 + 3 = 7
2. B
Et
1
SN + E1
Cl
Et
No rearrangement
 (6)
1
SN E1
Et Et Et
* +
x (2) (1) (2)

+
Et
(2)
Total = 2 + 5 = 7
3. A
Non-classical carbocation is formed
Ph
H2O 
(P) Ph Cl 
(Polar protic solvent) + Cl (SN1)
Carbocation is intermediate
 
(Q) Cl Ph S Na 
+ Cl
SN2
SPh
F F
KOH
(R) Ar SN OH
NO2 NO2
(carbanion intermediate)
Br2
(S) CCl 4 Formation of non-dassical carbocation.
4. B
CH2 Cl F
NO 2
Nu -M Nu
(A) (B) SN Ar
SN2
NO2 NO 2
-M
F
F
H
strong
(C) (D) base
NO 2
CH 3 (Benzyne)
Sterically inhibited
resonance
5. A-PR ; B-QR ; C-Q ; D –T
O
(1) Hg(OAc) 2, H2O

CH3 C CH3
(2) NaBH 4, HO
(A) CH3 C CH
(1) BH 3 : THF

CH3 CH2 CHO
(2) H2 O 2, HO
Both are addition reaction

I and II are functional isomers
Br
HBr
CH3 CH CH3
CCl 4
(I)
(B) CH3 CH CH2
(1) BH3 : THF


CH3 CH2 CHO
(2) H2O 2, HO
Both reactions are addition reaction

I and II are positional isomers
Na C CH
(C) CH CH Cl CH3 CH2 C CH
3 2
(I)
Br
(i) alc. KOH
CH3 C CH2 CH3 CH3 C C CH3
(ii) NaNH2 (II)
Br
I & II are positional isomers, (I) is nucleophilic substitution reaction, (II) is elimination reaction.
I
H2 O H 2O
SN1 
(D) (rearrangement)
T CH3 OCH3
CH3 OCH3
OCH3 + OCH3
OH OH
CH3 CH3
(A) (B)
H 3C
I H3 C
OCH3 H2 O  OCH3
SN1
(reaarangement)
H3 C
H 3C
H 2O
OCH3  OCH 3
H2O
OH
SN1
(reaarangement)
OCH3 +
OH OCH3
OH
H3 C (C)
H3 C (D)
B,C : Identical A, D : identical

A, B : diastereomers B, D : diastereomers
6. C
O EtBr OEt
(P)
Br 
EtO
(Q) E2
(R)   OEI
EtOH/H  -H
+ EtOH
E2
El Cl
(S) Et-Cl 
Na  ether
 Wurtz 
7. 4
CH3 CH3 CH3
CH3OH
+
Br OCH3 OCH3
substitution products
CH3 CH3
Elimination products
8. 3
OH +
H /D
(a)
E1
CH2 CH2 F CH CH2
(c) E1CB
NO2 NO2
H2O
(f) SN1
Cl
9. 6
Cl
O O
CH3 Cl , Cl , ,
O Et , OH ,CH3 CH CH2 , Cl , CH3 C N
     

NO2 Acid-Base Elimination
reaction addition
 or reaction
Elimination
reaction

Alkyl Halide DPP (With Solution) and Sheet

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Alkyl Halide DPP (With Solution) and Sheet

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CONTENT

Class : XII Time : 30 min. DPP # 1

No. SN2 here due to

x PCl 5 yNaNH2 CH3I

CH3 CH2Br CH2SH

Class : XII Time : 30 min. DPP # 2

No SN2 due to steric hindrance

No SN2 due to bredt’s rule

No SN2 due to double bond character with leaving group(-I)

(A) (B) (C) R C OCH (D)

1. NaNH2 2. CH3 CH2 I

Class : XII Time : 30 min. DPP # 3

(No SN1 reaction)

Br2 CH 3OH(aq.) Br2 CH 3OH(aq.)

Class : XII Time : 30 min. DPP # 4

Class : XII Time : 30 min. DPP # 5

(i) (ii) (iii) (iv)

More no. of –NO2 group at O/P, more rate of SNAr.

For halogens : -> + M

Class : XII Time : 30 min. DPP # 6

(P, Q are positional isomers)

Rate constant is highest for (ii) because aromatic product formed.

(2) (1) (2)

(i) (ii) (iii)

Class : XII Time : 30 min. DPP # 7

Two chiral center

(X) (Y) or Final product

Class : XII Time : 30 min. DPP # 8

G.I.  G.I.  G.I. 

Class : XII Time : 30 min. DPP # 9

(1) C C CH2 hiral with fixed configuration (E and Z)

(2) C C CH Chiral with fixed configuration (E and Z)

Class : XII Time : 30 min. DPP # 10

x (2) (1) (2)

Both are addition reaction

(B) CH3 CH CH2

(1) BH3 : THF

Both reactions are addition reaction

B,C : Identical A, D : identical

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