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Solutions Advanced Level Problem Solving - 2326

JEE 2023 | Chemistry

1.(B) 2.(D) E2 mechanism.

For 3 --- 4
3.(A); 4. (D)
In case of good leaving group (reaction proceed through stable transition state stability of T.S. by alkene
( IΘ good leaving group)

If leaving group is strong base reaction proceed through stable carbanion in transition state.

carbanion is more stable.  Hoffmann product is major.

For 5 – 7
5.(4), 6.(13), 7.(6)

8.(16)

9.(ABCD)
At  -position –M gp. prefer elimination.

10.(3)

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11.(D)

12.(C)

Both  -positions have identical hydrogen and give only one product.

13.(C) E2 depends upon - (1) strong base, (2) stable T.S. (3) leaving group ability.

14.(D)

Complex mixture means maximum number of alkene.

For 15–16
15.(5), 16.(3)

(B) is CH3CHO(Mo  44) and (C)is CH3CH2CH2COCH2CH2CH2CH3 (Mo  128)

17.(98)

(Mo  98)

18.(ACD)
In E2 anti-elimination take place, H and bromine must be anti to each other (III) is most favourable

because both hydrogen are anti to bromine most favourable for E 2 reaction. (II) is least reactive because
hydrogen and bromine both are on same side, (II) is inert toward E2 reaction.

19.(B) In presence of poor leaving group such as (fluorine), reaction proceed through stable carbanion in
transition state.

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20.(B)

21.(2)

HO  (CH 2 )3 C  CH can reacts with 2 mole of CH 3MgBr

22.(D)

Loss of chirality takes place during reaction.

For 23 – 24
23.(6), 24.(6)

25.(2) Pair of diastereomers will be formed.

Br O
Alcoholic NBS
| 1.KCN

26.(15) C3H7I  CH2  CH  CH3 
 CH2  CH  CH2   CH2  CH  CH2  C  CH3
KOH  2.MeMgBr
3.H3 O (D)
27.(ABD)
Informative question.
28.(A) Rate of reaction of alcohol with H—Br  Stability of C formed in R.D.S.
For 29 – 30
29.(2), 30.(3)

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31.(D)

32.(ACD)
Williamson’s ether synthesis is S N 2 not possible in 3° alkyl halide.

33.(C)

(Sulphur is better nucleophile than oxygen.) (But oxygen is better base than sulphur)
(A) is formed by acid-base reaction therefore oxygen will react.
(B) is formed by electrophile and nucleophile reaction therefore sulphur will react.
34.(A)

35.(C)

36.(6) 1-chloro-2-methylbutane (Pair of enantiomers)

2-chloro-2-methylbutane
2-chloro-3-methylbutane (Pair of enantiomers)
1-chloro-3-methylbutane
37.(ABD)

38.(ABC) Reactivity of carbonyl compounds with G.R.

1

Steric hindrance
39.(D) Refer module.
40.(ACD)
Reactivity with G.R.
Except aldehyde all other on reaction with Grignard reagent for 3° alcohol.

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41.(ABCD)

42.(4), 43.(7)

44.(A) Density  molecular mass.

45.(A) 46.(C)

47.(ABCD)
(A) Tertiary alkyl halides do not undergo S N 2 substitution.

(C) Alkyl chlorides, bromides, iodides give beilstein test. Alkyl fluorides do not.

(D) Nucleophilic substitution is easy in alkyl iodides as I is a good leaving group.

48.(AB)  -elimination is a reaction in which leaving group and hydrogen are eliminated from adjacent carbon
atoms.
(C) is an example of  -elimination.

49.(ABCD)

50.(ABCD)
Refer module (Grignard’s reagent).

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