A neutral compoundon acid hydrolysis produces two compounds B (C4H8O) and C (C6H10O2). B on treatment with SOCl2 gives D (C4H7Cl) which on further treatment with aqueous solution of KCN followed by hydrolysis of product yielded ‘E’ (C5H8O2). E on reducing with LiAlH4 gives F (C5H10O), which on heating with conc. sulphuric acid solution yields G (C5H8). G on treatment with HCl yields Identify correct options.

Engineering

Chemistry

Nucleophilic Substitution

Elimination Reactions

Alkene

Question

A neutral compound

on acid hydrolysis produces two compounds B (C₄H₈O) and C (C₆H₁₀O₂). B on treatment with SOCl₂ gives D (C₄H₇Cl) which on further treatment with aqueous solution of KCN followed by hydrolysis of product yielded ‘E’ (C₅H₈O₂). E on reducing with LiAlH₄ gives F (C₅H₁₀O), which on heating with conc. sulphuric acid solution yields G (C₅H₈). G on treatment with HCl yields

Identify correct options.

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The compound A is an ester that hydrolyzes to B (C₄H₈O) and C (C₆H₁₀O₂). B is an aldehyde, likely butanal, which is converted to acid chloride D, then to cyanide, and hydrolyzed to E, a carboxylic acid (C₅H₈O₂). Reduction of E gives F, an alcohol (C₅H₁₀O), which dehydrates with conc. H₂SO₄ to alkene G (C₅H₈). G reacts with HCl via Markovnikov addition, forming the product shown. The correct option is the one where HCl adds to the double bond, resulting in a tertiary chloride.

Final Answer: $C_{5} H_{9} Cl$ with Cl on tertiary carbon.