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Hinsberg Test

Identify the ...

Question

Identify the correct statement(s) about the above sequence of reactions :

compound (A) is formed through

S_{N}

reaction

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compound (C) on reduction with

L i A l H_{4}

forms a product which on dehydration given cyclohexene.

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compound (A) requires two moles of hydrogen for complete reduction.

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compound (C) on Schmidt's reaction gives a product which reacts with

H N O_{2}

to give (D) as major product. compound (D) on dehydration gives cyclopentene

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Solution

The correct options are
A compound (A) is formed through $S_{N}$ reaction
B compound (C) on reduction with $L i A l H_{4}$ forms a product which on dehydration given cyclohexene.
D compound (C) on Schmidt's reaction gives a product which reacts with $H N O_{2}$ to give (D) as major product. compound (D) on dehydration gives cyclopentene
The statements (A), (B) and (D) are correct. The statement (C) is incorrect.

(A) Compound (A) is formed through nucleophilic substitution reaction. Chlorine atoms are replaced with cyanide groups.

(B) Compound (C) (cyclopentanecarboxylic acid) on reduction with $L i A I H_{4}$ forms cyclopentylmethanol which on dehydration gives cyclohexene. Dehydration step involves rearrangement in which five member ring expands into six member ring.

(C) Compound (A) requires one (not two) mole of hydrogen for complete reduction.

(D) Compound (C) (cyclopentanecarboxylic acid) on Schmidt's reaction gives cyclopentanamine ( $- C O O H$ group is replaced with $- N H_{2}$ group) which reacts with $H N O_{2}$ to give (D) (cyclopentanol) as major product. Compound (D) (cyclopentanol) on dehydration gives cyclopentene.

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