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JEE Advanced 2023Paper 1
Exam
JEE Advanced
Year
2023
Paper
Paper 1
Subject
Chemistry
Chapter
Haloalkanes and Haloarenes

JEE Advanced 2023 · Paper 1 · Chemistry · Haloalkanes and Haloarenes

Match the reactions in List-I with the features of their products...

Match the reactions in List-I with the features of their products in List-II and choose the correct option.

List I List II
(P)( P )

(−)−1−Bromo−2−ethylpentane(Singleenantiomer)→SN2reactionaq.NaOH\mathop{\left(-\right) - 1 - Bromo - 2 - ethylpentane}_{( Singleenantiomer )}\mathop{\to}_{{S}_{N}2reaction}^{aq . NaOH}

11 Inversion of configuration
(Q)( Q ) (−)−2−Bromopentane(SingleEnantiomer)→SN2reactionaq.NaOH\mathop{\left(-\right) - 2 - Bromopentane}_{\left(SingleEnantiomer\right)}\mathop{\to}_{{S}_{N}2reaction}^{aq . NaOH} 22 Retention of configuration
(R)( R ) (−)−3−Bromo−3−methylhexane(SingleEnatiomer)→SN1aq.NaOH\mathop{\left(-\right) - 3 - Bromo - 3 - methylhexane}_{\left(SingleEnatiomer\right)}\mathop{\to}_{{S}_{N}1}^{aq . NaOH} 33 Mixture of enantiomers
(S)( S ) Match the reactions in List-I with the features of their products in List-II and choose the correct option. List I List 44 Mixture of structural isomers
55 Mixture of diastereomers

Options

  1. AP→1;Q→2;R→5;S→3P \to 1; Q \to 2; R \to 5; S \to 3
  2. BP→2;Q→1;R→3;S→5P \to 2; Q \to 1; R \to 3; S \to 5
  3. CP→1;Q→2;R→5;S→4P \to 1; Q \to 2; R \to 5; S \to 4
  4. DP→2;Q→4;R→3;S→5P \to 2; Q \to 4; R \to 3; S \to 5

Correct answer

B. P→2;Q→1;R→3;S→5P \to 2; Q \to 1; R \to 3; S \to 5

Step-by-step solution

1−Bromo−2−ethylpentane(Singleenantiomer)→SN2reactionaq.NaOH2−ethylpentanol\mathop{1 - Bromo - 2 - ethylpentane}_{( Singleenantiomer )}\mathop{\to}_{{S}_{N}2reaction}^{aq . NaOH}2 - ethylpentanol

In the above reaction the chiral carbon is not involving in the reaction as SN2{S}_{N}2 reaction takes place via formation of transition state but not through formation of intermediate.

Match the reactions in List-I with the features of their products in List-II and choose the correct option. List I List

In the above reaction, bromine attached to chiral carbon, and it is involving in SN2{S}_{N}2 reaction. Hence, the alcohol formed in inversion configuration.

Match the reactions in List-I with the features of their products in List-II and choose the correct option. List I List

The substrate is undergoing SN1{S}_{N}1 reaction. It takes place via formation of carbocation. Carbocation as planar, hence, the alcohol product formed is racemic mixture as nucleophile can attack from both the planes.

Match the reactions in List-I with the features of their products in List-II and choose the correct option. List I List

The substrate is undergoing SN1{S}_{N}1 reaction. It takes place via formation of carbocation. Carbocation as planar, hence, the two alcohol products are formed as nucleophile can attack from both the planes but the substrate already having the chiral centre, the mixture formed is diastereomeric mixture.

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