DPP Alkyl Halide PDF

CONTENT
S.No Pages
1. DPP-1 04 – 05
2. DPP-2 06 – 07
3. DPP-3 08
4. DPP-4 09 – 10
5. DPP-5 11 – 12
6. DPP-6 13 – 16
7. DPP-7 17 – 18
8. DPP-8 19
9. DPP-9 20 – 21
10. DPP-10 22 – 23
11. DPP-11 24 – 25
12. DPP-12 26 – 27
13. DPP-13 28
14. DPP-14 29
15. DPP-15 30 – 31
16. DPP-16 32 – 33
Let's Crack it !
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ORGANIC CHEMISTRY
Daily Practice Problems Target IIT-JEE
Class : XII Time : 45 min. DPP # 1

Compound : (A) (B) More reactive towards SN2
I
1. I
Br
2. Br
Br CH2Br
3.
Ph – CH – Br
4. Ph CH2 Br
CH3
CH3 CH3
H Br H Br
5.
Et D
H Cl
Cl H
6.
H H
7. I I
Br
8.
Br
Br Br
9.
CH2Br Br
10.
Br
Br
11.
I Br
12.
13. [CH3 X] = 0.1 M [CH3–X] = 0.2 M

14. [Nu–] = 0.1 M [Nu–] = 0.2 M
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15. Identify the product in each reaction
(a) CH3CH2Cl + HO– 
(b) CH3CH2Br + HS– 
(c) CH3CH2I + RO– 
(d) CH3CH2Br + RS– 
(e) CH3CH2Cl + –NH2 
(f) CH3CH2Br + –CCR 
(g) CH3CH2I + –CN 
16. Which alkyl halide would you expect to be more reactive in an SN2 reaction with a given nucleophile ?
(a) CH3CH2CH2Br or CH3CH2CH2I (b) CH3CH2CH2Cl or CH3OCH2Cl
CH3 CH2CH3 CH3 CH3

| | | |
(c) CH3CH2CHBr or CH3CH2CHBr (d) CH3CH2CH2CHBr or CH3CH2CHCH2Br
(e) CH2CH2Br or CH2CHCH3 (f) CH2Br or Br

|
Br
O
Cl , Cl
(g) CH3CH = CCH3 or CH 3CH=CHCHCH 3 (h)
| | Ph Ph
Br Br
17. Which reaction in each of the following pairs will take place more rapidly ?
(a) CH3Br + HO–  CH3OH + Br–
CH3Br + H2O  CH3OH + HBr
(b) CH3I + HO–  CH3OH + I–
CH3Cl + HO–  CH3OH + Cl–
+ –
(c) CH3Br + NH3  CH3NH3 + Br
CH3Br + H2O  CH3OH + HBr
(d) CH3Br + HO– 

DMSO
 CH3OH + Br
–
CH3Br + HO– 
EtOH
 CH3OH + Br
–
Et 2O
(e) CH3Br + NH3  + –
 CH3NH3 + Br
EtOH
CH3Br + NH3  + –
 CH3NH3 + Br
18. What nucleophiles could be used to react with butyl bromide to prepare the following compounds ?
(a) CH3CH2CH2CH2OH (b) CH3CH2CH2CH2OCH3 (c) CH3CH2CH2CH2SH
(d) CH3CH2CH2CH2SCH2CH3 (e) CH3CH2CH2CH2NHCH3 (f) CH3CH2CH2CH2CN
ORGANIC CHEMISTRY

Subjective Problems :
Q. X = The number of compounds do not show SN2.
CH2–Br Br Cl
Cl
1. 2. 3. 4.
Cl F
5. 6. 7. 8.
Cl Cl
Cl
Cl
9. 10.
CH2–CH2–CH2Br
11.
Q. Identify the product

CH3
12. H
C – O – H + Cl – SO2 CH3 Pyridine
C6H5CH2 25ºC
CH3
H
13. CH3CO2 K + C – OTs Acetone
C6H5CH2 SN2
Cl
I
D H
14. KSH 15. KSH
H D
CH3
CH2–Br
Cl
Ph–SNa Ph–SNa
16. 17.
I
Cl Cl
18. aq.KOH 19. KI

acetone
Cl
CH3
H Br aq.KOH
20. Cl – CH = CH – CH2 – Cl aq.KOH 21. D H
Ph
CH3
H I NaCN NaCN
22. 23. 2R–chlorobutane
Ph
ORGANIC CHEMISTRY

Predict all the major product(s) along with stereochemistry of the following reaction sequences :
NaNH2 CH – I H Cold . KMnO 4
1. CH3 – C  CH   ( A )  3
 (B ) 2 (C)    Product(s)
Pd–BaSO 4
NaNH 2 Et – I H2 Cold . KMnO4

2. CH3 – C  CH   ( A )  (B)    (C) 
Pd–BaSO
   Product(s)
4
NaNH2 CH – I
3. CH3 – C  CH   ( A )  
3
 (B ) H2 (C) 
Br2
 Product(s)
Pd–BaSO CCl 4 4
NaNH 2 Et – I H2 Br2
4. CH3 – C  CH    ( A )   (B)   (C )  Product(s)
Pd– BaSO 4 CCl 4
NaNH2 CH3 – I Na Cold . KMnO4

5. CH3 – C  CH   ( A )    (B)   (C)    Product(s)
Liq. NH3
NaNH2 Et – I Na Cold . KMnO4

6. CH3 – C  CH    ( A )   (B)   (C)     Product(s)
Liq. NH3
NaNH2 CH3 – I Na Br2

7. CH3 – C  CH   ( A )    (B)   (C)  Product(s)
Liq. NH3 CCl4
NaNH2 Et – I Na Br2
8. CH3 – C  CH   ( A )   (B)   (C)  Product(s)
Liq. NH3 CCl4
2
NaNH 2 Et – I Hg H2
9. CH3 – C  CH   ( A )  (B )   (C ) 
H SO
 Product(s)
Ni
2 4
2NaNH2 CH3 –  Et – 
10. H – S – CH2 – (CH2)8 – OH  ( A )    (B)   Product(s)
(1 mole ) (1 mole )
2 NaNH2 CH –  Et – 
11.   ( A )  
3
 (B)   Product(s)
(1 mole ) (1 mole )
2
NaNH2 Hg
12. Ph – C  CH   (A) (B)  Pr
Product(s)
H2 SO4
NaNH2 CH3–I
OH (A) (B)
13.
Na CH3–I
(C) (D)
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ORGANIC CHEMISTRY

Compound : (A) (B) More reactive towards SN1
I
1. I
Br
2. Br
Br CH2Br
3.
4. Ph CH2 Br Ph – CH – Br
CH3
CH3
CH3
H Br
5. H Br
Et
D
H Cl
Cl H
6.
H H
7. I I
Br
8.
Br
Br Br
9.
CH2Br Br
10.
Br
Br
11.
I Br
12.
13. [CH3 X] = 0.1 M [CH3–X] = 0.2 M

14. [Nu–] = 0.1 M [Nu–] = 0.2 M
S.No. Compound Compare rate of SN2 Compare rate of SN1
15.
16.
17.
18.
19.
20.
21.
22.
23.
24. CH3 – O – CH2 – Br CH3 – CH2 – CH2 – Br
25.
26.
ORGANIC CHEMISTRY

1. Which of following compound will not undergo nucleophilic substitution reaction
Cl Cl Cl Cl
(A) (B) (C) (D)
2. Most reactive toward SN2

O
(A) (B) Cl (C) Cl (D) Ph – C – CH2 – Cl

Cl
3. R–I R – Br R – Cl R–F
(a) (b) (c) (d)
rate of SN2 is
(A) a > b > c > d (B) b > a > c > d (C) a = b = c = d (D) d > c > b > a
4. R–I R – Br R – Cl R–F
(a) (b) (c) (d)
rate of SN1–
(A) a > b > c > d (B) b > a > c > d (C) a = b = c = d (D) d > c > b > a
Cl Cl
H2O reaction ––(1) H2O reaction ––(2)

5.
reacton (1) & reaction (2) are

(A) SN1, SN1 (B) SN1, SN2 (C) SN2, SN1 (D) SN1, no reaction
Cl
H2O reaction ––(1)
6. Cl ; reaction -(1) & reaction-(2) are
H2O
reaction ––(2)
(A) SN1, SN1 (B) SN1, SN2 (C) SN2, SN1 (D) SN1, no reaction
7. Most reactive towards SN1

(A) Me – O – CH2 – Cl (B) Me – NH – CH2 – Cl
O
(C) Me – C – CH2 – Cl (D) Me – CH2 – CH2 – Cl
8. Most reactive towards SN1
Me
(A) Me – O – CH2 – CH3 (B) Me – CH 2 – O – CH – Me
Me
(C) Me – CH2 – O – C – Me (D) Me – O – C
Me
9. Which of following reaction is SN21

(A) R2 CuLi + H2C = CH – CH2 – Cl (B) RMgX + H2C = H2C – CH2 – Cl
14 14
(C) NaI + CH3 – Cl (D) Br EtOH
HBr
10. H2C = CH – CH2 – OH   (A) , Product (A) is -
14 SN11
14
(A) H2C = CH – CH2 – Br (B) H2 C = CH – CH2 – Br
14
14
(C) CH2 – CH = CH2 (D) CH 3 – CH – CH 2 – OH
|14 |
Br Br
11. Correct order of leaving group.
CH2 CH2
O O
(A) > (B) I <N N (C) CH3 – C – O < CH3 – S – O (D) All
O
NO2
12. Reactivity : Circle the reaction that reacts FASTER by SN2 in each pair :
(1) NaOCH3 (2) H O (3) NaOH

Cl   I  2
 Cl  
NaOCH3 NaOH NaOH

Br   I  
Cl
13. Encircle whichever of the following :

Br
|
(a) undergoes an SN2 reaction more rapidly, CH3 – Br or CH3 – CH – CH3
Br
|
(b) undergoes an SN1 reaction more rapidly, CH3–Br or CH – CH – CH
3 3
Br
(c) undergoes an SN2 reaction more rapidly, or
Br
(d) undergoes an SN1 reaction more rapidly, (CH3)3C – Br or (CH3)3C – I
Br
Br
(e) undergoes an SN1 reaction more rapidly, or
ORGANIC CHEMISTRY

1. Which of the following alkyl halides will you expect to give the highest yield of substitution products under conditions
favourable to a bimolecular reaction?
(A) CH3CH2CH2CH2CH2Br (B) CH3CH2CH2CH—CH3
|
Br
Br
|
(C) CH3CH2—CH—CH2Br (D) CH3CH2—C—CH3
| |
CH3 CH3
2. In the SN2 reaction of cis-3-methylcyclopentyl bromide with alkali, the product formed is
(A) a cis alcohol
(B) a trans alcohol
(C) an equimolecular mixture of cis and trans alcohols
(D) there is no reaction
3. Which of the following alkyl halides is unreactive in an SN2 reaction?

(A) Primary (B) Secondary (C) Tertiary (D) Methyl chloride
4. In SN2 reactions, the order of reactivity of the halides CH3X, C2H5X, n-C3H7X, n-C4H9X is
(A) CH3X > C2H5X > n-C3H7X > n-C4H9X (B) C2H5X > n-C3H7X > n-C4H9X > CH3X
(C) C2H5X > n-C3H7X > n-C4H9X > CH3X (D) n-C4H9X > n-C3H7X > C2H5X > CH3X
5. Correct statement regarding SN2 is
(A) If conc. of Nu and substrate will be respectively doubled and tripled then Rate of reaction of SN2 remains
same
(B) Rate of SN2 increases if number of branches increases in isomeric bromobutane
(C) Approach of Nu takes place from frontside as well as from backside in SN2 mechanism
(D) Approach of Nu always takes place from backside in SN2 mechanism
H F
6. + NaI (one mole)   Product will be
acetone
Br H
I F H F
(A) (B)
H H I H
H H H I
(C) (D)
Br I Br H
7. Hydrolysis of methyl bromide takes place much faster in the presence of

(A) KF (B) KI (C) KBr (D) KCl
8. Treatment of (S)-2-bromobutane with sodium hydroxide results in the production of a compound with an (R)
configuration. The reaction has most likely taken place through :
(A) an SN1 mechanism (B) an SN2 mechanism
(C) both SN1 and SN2 reaction (D) cannot be determined
9. Which of the reactions shown below will be faster ?
KOH KOH
Reaction 1:  ; Reaction 2: 
H2O Crown ether
(A) Reaction 1 (B) Reaction 2

(C) Both have equal rates of reaction (D) Cannot be predicted
KSH
10.  
(A) (B) (C) (D)
NaOH
11.  A. A is:
excess
(A) (B) (C) (D)
12. Give the structure of the reactant that could be used to convert iodoethane into given compounds ?
S – CH2–CH3
CH3
   
SK SK
(A) (B)
CH3 CH3
   
SK SK
(C) (D)
CH3 CH3
13. Transition state of given SN2 is
CH2 – Br CH2 – O – R
R  O
  
SN2 reaction
+
+
 +
OR  (+) +
OR
H
H
(A) H (B)
H
Br
 Br
 (+)
+
+
 +
OR  (–) +
OR
H
H
(C) H (D)
H
Br
 Br
 (–)
Paragraph for Question Nos. 14 to 16

Substitution is the replacement of one group by another. The reaction happens at the saturated carbon atom so the
reaction is a nucleophilic substitution at a saturated carbon atom.
H H
 Nucleophil e attacks at the H H
PhS
same time as the
Ph Cl            Ph
leaving group goes PhS
14. In which of reaction SN1 & SN2 product are same (excluding stereoisomers)
Cl Cl
Cl
Cl
(A) (B) (C) (D)
O
15. In which of following SN1 & SN2 are present ?
Cl
(A) (B) (C) (D) Cl

Cl
Cl
16. In which of following reaction retention of configuration doesn't take place in overall reaction ?
CH3 T
Na CH I PBr3 NaI
(A) H OH  3 
  (B) (B) H OH   (A) (C)
Pyridine
D O
Ph
Br Br
NaI
(C) HO(aq.) +  (D) KSH
(A)   (B)
O
Match the column :
DMF
17. Nu– + Me–OTs  Me–Nu + TsO–
25
This is a SN2 reaction where nucleophile attack Me–OTs in the rate determining step to give the product. Rate of
this reaction increases with concentration as well as nucleophilicity of the nucleophile. Match the column I with
column II for the above reaction
Column I Column II
(Nucleophile) (Relative rate)
(A) F (P) 3.25
(B) Cl  (Q) 6.25
(C) Br (R) 1.0
(D) I (S) 7.75
Subjective :
18. What Nu is needed to convert A to each substitution product
+
N
(i)
N=O
O
Major
(ii)
Br
SCH3
A
(vii) (iii)
N3
CN (iv)
O
(vi)
Major (v)
Passage : (1 to 11)
An important route to synthesize unsymmetrical ether is williamson ether synthesis. This reaction is an
example of Nucleophilic substitution reaction. (SN2 Reaction)
It involves the reaction generally between alkyl halide and alkoxide ion. 1° Alkyl halide and 1° Alkoxide ion
gives best yield of ether during this reaction.
1. Best method to prepare O – CH3 is
the combination of
(A) KOH CH3I (B) OH Na CH3I

OH
Na
Cl
(C) MeOH (D) (A) & (B) both
2. H OH NaH (X) Me– I (Y)
Identify (Y)
H OMe
(A) (B) MeO H (C) H OMe (D) None of these
3. Identify product EtO + Ph – CH2 – Cl

O
(A) Ph O (B) Ph O (C) CH2 = CH2 (D)
Ph
4. Which of the following is an appropriate sets of reactant for the preparation of 1-methoxy-4-Nitrobenzene
Br ONa
(A) + CH3ONa (B) + CH3Br

NO2
ONa ONa
(C) + CH3Br (D) + EtONa

NO2 NO2
O
5. Suitable combination of reactant to prepare Ph
ONa
ONa + Br
(A) Ph (B) + Br
Ph
Br Br
(C) + KO (D) + NaO
Ph Ph
CH3
H OK EtBr
6. Product
H CH3
Et
Correct stereochemical relationship between reactant and product will be
(A) Enantiomer (B) Diastereomer (C) Structural isomer (D) None of these
7. Which of the following can’t be prepared by willamson ether synthesis
(A) O (B) O
(C) O (D) O
8. Incorrect statement regarding williamson ether synthesis is

(A) Less hindered halide is used in this reaction (B) Less hindered alkoxide ion is used in this reaction
(C) Mechanism of reaction will be SN2 (D) More hindered halide is used in this reation
9. Which of the following ether is not synthesied by willamson ether synthesis
(A) O–CH3 (B) O
(C) (D) O
O
10. RO Na + R – L ROR + Na L
Rate of reaction will maximum when L is
(A) CF3SO3– (TRIFLATE ION) (B) CH3 SO2 (p-Toluene sulphonate)
(C) Br– (D) I–
11. Identify the products
A KH TsCl C
OH
K
B
12. The best combination for the preparation of ether by Williamson’s synthesis are
(A) (CH3)3 C Br and CH3O Na (B) (CH3)3 C Br and CH3 OH
(C) CH3 Br and (CH3)3 CONa (D) CH3 Br and (CH3)3 C OH
Q. Write the product of the given reactions ?
PCl5
(1) R – OH
PCl5
(2) Ph – CH2 – OH
PCl5
(3) CH3 – O – CH3
O
(4) PCl5
O
(5) PCl5
OH
O
(6) PCl5
OEt
O
(7) PCl5
O
(8) PCl5
Ph – C – CH3
O
PCl5
O
(9)
O
O
(10) PCl5
NH 2
O PCl5
(11)
O–CH3 SOCl2
(12)
OH
PBr3
(13) OH
(14) Pent-1-yn-3-ol PBr3
Me
SOCl2
15. H OH ‘P’
D
Product ‘P’ is
(A) Inverted Product (B) Racemic (C) Retention Product (D) Meso
Q. Identify the missing structure in each reaction ?
Cl
1. 15%NaOH
160ºC
NO2
Cl
O2 N NO2
H2O
(A) acid
2.
NO2
Br
NO2
CH3O
3.
NO2
Br
NO2
CH3O
4.
Br
Br
NO2
CH3–CH2–NH2
(A) HO (B)
5.
NO2
F OH
HO (A) H
6. mesenheimer
complex
NO2 NO2
F
KOH/
7.
NO2
NO2
KOH/
8.
Br
Br
CH3
9. KNH2
(A)
liq.NH3 (major)
Cl
OCH3
Cl
10. KNH2
(B)
liq.NH3 (major)
Br
CH3ONa
11. (A)
NO2
Energy profile diagram of given reaction is
12. Most reactive towards SN–Ar

Br Br Br Br
NO2
(A) (B) (C) (D)
NO2 NO2
NO2 NO2 NO2
13. Steps involve in given reaction
F OH
HO
NO2 NO2
(A) Addition-substitution (B) Addition-Elimination
(C) Elimination-Addition (D) Substitution-elimination
14. Most reactive towards SN–Ar is
Cl Br I
F
(A) (B) (C) (D)
NO2 NO2 NO2 NO2
SNo. Compound Structure of Product Structure of Product
(When react with conc. HI) (When react with conc. HI excess)
1. O
2. O
O
3. Ph CH3
4. Ph O
O
5. Ph Ph
6. PhOH
7. O
8. CH3 – CH2 – OH
9. O
O
10.
11. O
Ph
12.
Ph O
13. O – Et
14. Ph O
15. O
S.No. Compound Structure of Product
(After reaction with dilute H3O+)
18
16. Ph – O – CH 3
17.
O
18.
OCH3
19. Ph – O
20. Ph – O – CH3
21.
O O
CH3
22.
O
23. Ph–O–CH2–CH2–CH–CH–O–CH2–CH3
CH3
24.
O
25.
O
26.
O
27. Ph – O – Et
28. O
29. O
30. Ph – O – CH = CH2
1. Compare rate of dehydration (acid-catalyzed)
OH
OH OH OH
OH OH
| |
(a) (b) (c)
OH
OH
|
(d) | OH (e)
OH
2. Predict the major product of acid-catalyzed dehydration of alcohols

(A) 2-pentanol (B) 1-methyl cyclopentanol
(C) 2-methyl cyclohexanol (D) 2, 2-dimethyl-1-propanol
3. Identify-Product
CH3 CH3 CH3
| H2SO4 | | H2SO4
(a) CH 3 – C – CH2 (b) CH3 – CH2 – C – CH – CH3
| | |
OH OH OH
OH
|
—CH2 – OH H3PO4 —CH – CH2 – CH3 H3PO4
(c) (d)
OH
| CH3
+
| H+
H
(e) (f) CH3 – CH2 – CH – C – CH3
| |
OH CH3
OH
|
OH H+ H
+
(g) (h) A+B
CH3
H+
|
H H H+
(i) CH A+B (j) A+B
3 OH
|
OH
OH OH
(k) KHSO 4 (l) | H2SO4
170ºC
OH OH
H2SO4 |
(m) (n) H2SO4
|
CH3
CD3
| OH
OH
+
H H+
(o) (p)
OH
CH3
Cl
D D H
+
H3PO4
+
(q) D D H (r) (s)
OH
OH
4. Write-Mechanism
OH
OH
H
(a)
5°C
CH3
CH3
CH3 – CH2 – CH2 – CH2 – C – CH2 – OH H
C = CH – CH2 – CH2 – CH2 – CH3
(b)
CH3
CH3
Free
energy
5.
CH3
RCH3 –C–CH2 –R A
OH2 B
Progress of reaction
Products A and B respectively
CH3 CH2 CH3 CH2

(A) H2C=C–CH2–R and H3C–C–CH2–R (B) H3C–C–CH=CH2 and H3C–C–CH2–R
CH3 CH3
(C) H3C–C=CH–CH3 and H2C=C–CH2–CH3 (D) H2C=C–CH2–R and H3C–C=CH–R
CH3 CH3
6. Which one of following alcohol would dehydrate fastest when heated with acid
CH 3 CH3 CH2–OH CH3

OH OH
(i) (ii) (iii) (iv)
OH
(A) i > ii > iii > iv (B) iii > ii > iv > i (C) iv > ii > i > iii (D) ii > iii > i > iv
E1 (Elimination unimolecular)
TOTAL PRODUCTS
S.No. Compound Excluding Stereo isomer Including Stereo isomer
Br
1. EtOH
(E1)
EtOH
2. Cl (E1)
3. EtOH
Br (E1)
EtOH
4. (E1)
Cl
EtOH
5. Br (E1)
Cl
EtOH
6.
(E1)
Cl
CH3
EtOH
7.
(E1)
CH3 Cl
EtOH
8.
(E1)
CH3 Cl
EtOH
9. (E1)
CH3
CH3 Cl
EtOH
10. (E1)
CH3
11. A B ? C
O
(A) Cl / NaOH / H2SO 4 (B) / H2SO4 / H2O
(C) OH / HBr / CH3O

– (D) OH / HBr / CH3O
–
OH
H3C–CH–CH–CH3 + H2SO4 A product as major so A is
12.
CH3
CH3 CH2 CH3

(A) H3C–CH–CH=CH2 (B) H3C–C–CH2–CH3 (C) H3C–C=CH–CH 3 (D) None of these
(A) Dehydrohalogenation
TOTAL PRODUCTS
Excluding Stereo isomer Including Stereo isomer
Br alc. KOH
1. E2
alc. KOH
2. E2
Br
alc. KOH
3.
E2
Br
alc. KOH
4. E2
Br
Br
5. alc. KOH
E2
Br alc. KOH
6. E2
Cl
7. alc. KOH
E2
Cl
alc. KOH
8.
E2
(B) Dehydration of alcohol
+
H
9. (E1)
OH
+
H
10. (E1)
OH
OH
+
11. H
(E1)
+
H
12. (E 1)
OH
OH
+
13. Ph H
(E1)
OH
+
14. H
(E1)
Identify Products :
H3 O HI
1. Ph – CH2 – O – Ph (A) + (B) (C)
H3O HI
2. CH3 – CH2 – O – CH2 – CH3 A+ B (C)
OH
PBr3 alc . KOH
3. (A) (B)
Br
aq KOH SOCl 2 NaNH2
4. (A) (B) (C)
Br
2Na NH2
5. (A)
Br
Br
2Na NH2
6. (A)
Br
OH
PCl5 NaI
7. (A) (B)
acetone
Cl
aq. KOH H2SO 4
8. (A) (B)
Cl
Cl CH3 3NaNH 2
9. (A)
Cl
alc . KOH NaNH2 Na NH2 CH3 I
10. (A) (B) (C) (D)
Cl
Cl Cl
H H alc . KOH NaNH2 2NaNH2 2EtI
11. (A) (B) (C) (D)
H H
Find value of (x) and (y)
Cl
( x ) NaNH2 ( y ) CH3 – I
12. (A ) CH3 – C C – CH3
Cl
Cl
( x )NaNH 2 ( y ) CH3 I
13. (A) CH3 – C C – CH3
Cl
Cl Cl
14. ( x ) NaNH2 ( y ) Ph – CH2 – I Ph – CH2 – C C–C C – CH – Ph
Cl Cl
Q. Identify major product and type of reaction (SN1 / SN2 /E1/E2).
S. No. Reaction SN1 / SN2 /E1/E2

Cl
1. alc.KOH
NaNH2
2.
Br
t-BuOK
3.
Br
CH2–Cl
CH3O
4.
CH3
H Cl NaI
5. acetone
Et
Cl
H D KSH
6. H D
CH3
Cl
7. Ph–S
Br
8. KCN
Br
NMe3
9. EtO
10. EtO
S. No. Reaction SN1 / SN2 /E1/E2
H2O
11.
Br
Br
12. H2O
Br
13. EtOH
14.
EtOH
15.
Br
EtO
Br
16. NaI
acetone
Br
Br
17. NaI
acetone
Br
18. aq.KOH
Br
19. alc.KOH
Ph
20. H2O
Ph – C – Et
Br
21. H2SO4
OH
H2SO4
22.
OH
CH2–OH
23. PBr3
Pyridine
1. No. of possible product shown by given compound ?
S. No. Compound SN1 SN2 E1 E2

(a)
Br
(b)
Br
(c) Cl
Cl
(d)
(e)
Br
Br
(f)
2. Calculate the total number of SN1 + E1 products including stereoisomers ?

S.No. Compound SN1 + E1 products
(a) Br
(b)
Cl
(c) Br
Br
(d)
Br
(e)
3. Which of following is correctly matched
CH 3 +
CH3 +
H2O/H 1
H2O/H 1
(A) H3C–CH2–O–C–CH3 SN (B) H3C–C–CH2 SN
CH 3 O
Cl NaNH2
E1
(C) H D KSH
SN
1
(D)
H D Br
CH3
4. Identify correct order of reactivity for SN1 reaction
Br Br Br
(i) (ii) (iii)
(A) i > ii > iii (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii
5. Which of the following is an example of SN1

– –
(A) CH3Br + OH– CH3–OH + Br– (B) H3C–CH–CH3 + OH CH3–CH–CH3 Br
Br OH
CH3
H2 O – –
(C) H3 C – CH2 – OH H2 C CH2 (D) H3C–C–Br + OH (H3C)3C–OH + Br
CH3

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CONTENT

Class : XII Time : 45 min. DPP # 1

13. [CH3 X] = 0.1 M [CH3–X] = 0.2 M

(a) CH3CH2Cl + HO– 

(b) CH3CH2Br + HS– 

(c) CH3CH2I + RO– 

(d) CH3CH2Br + RS– 

(e) CH3CH2Cl + –NH2 

(f) CH3CH2Br + –CCR 

(g) CH3CH2I + –CN 

(a) CH3CH2CH2Br or CH3CH2CH2I (b) CH3CH2CH2Cl or CH3OCH2Cl

CH3 CH2CH3 CH3 CH3

(e) CH2CH2Br or CH2CHCH3 (f) CH2Br or Br

CH3Br + H2O  CH3OH + HBr

(d) CH3Br + HO– 

Class : XII Time : 45 min. DPP # 2

Q. X = The number of compounds do not show SN2.

Q. Identify the product

18. aq.KOH 19. KI

Class : XII Time : 45 min. DPP # 3

NaNH 2 Et – I H2 Cold . KMnO4

NaNH2 CH3 – I Na Cold . KMnO4

NaNH2 Et – I Na Cold . KMnO4

NaNH2 CH3 – I Na Br2

Class : XII Time : 45 min. DPP # 4

13. [CH3 X] = 0.1 M [CH3–X] = 0.2 M

24. CH3 – O – CH2 – Br CH3 – CH2 – CH2 – Br

Class : XII Time : 45 min. DPP # 5

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

2. Most reactive toward SN2

(A) (B) Cl (C) Cl (D) Ph – C – CH2 – Cl

H2O reaction ––(1) H2O reaction ––(2)

reacton (1) & reaction (2) are

H2O reaction ––(1)

6. Cl ; reaction -(1) & reaction-(2) are

7. Most reactive towards SN1

(A) Me – O – CH2 – CH3 (B) Me – CH 2 – O – CH – Me

(C) Me – CH2 – O – C – Me (D) Me – O – C

9. Which of following reaction is SN21

11. Correct order of leaving group.

(1) NaOCH3 (2) H O (3) NaOH

NaOCH3 NaOH NaOH

13. Encircle whichever of the following :

Class : XII Time : 45 min. DPP # 6

3. Which of the following alkyl halides is unreactive in an SN2 reaction?

5. Correct statement regarding SN2 is

(D) Approach of Nu always takes place from backside in SN2 mechanism

7. Hydrolysis of methyl bromide takes place much faster in the presence of

9. Which of the reactions shown below will be faster ?

(A) Reaction 1 (B) Reaction 2

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

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

Paragraph for Question Nos. 14 to 16

15. In which of following SN1 & SN2 are present ?

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

18. What Nu is needed to convert A to each substitution product

1. Best method to prepare O – CH3 is

(A) KOH CH3I (B) OH Na CH3I

2. H OH NaH (X) Me– I (Y)

3. Identify product EtO + Ph – CH2 – Cl

(A) + CH3ONa (B) + CH3Br

(C) + CH3Br (D) + EtONa

8. Incorrect statement regarding williamson ether synthesis is