Methanal is treated with $CH X_{3} CH X_{2} MgBr$ followed by $H X_{3} O X^{+}$ to give A. A reacts with $PBr X_{3}$ to give B, B with $KCN$ to give C, and C is hydrolysed with aqueous acid to give D. D is treated with $Br X_{2}$ and a trace of red phosphorus and then with excess $NH X_{3}$ to give E. E is

A2-aminobutanoic acid
B2-aminopropanoic acid
C3-aminobutanoic acid
D4-aminobutanoic acid

Answer: A

A is propan-1-ol, B is 1-bromopropane and C is butanenitrile. Hydrolysis gives butanoic acid (D). The Hell-Volhard-Zelinsky reaction brominates the alpha carbon (2-bromobutanoic acid) and ammonia substitutes the bromine to give

CH X_{3} CH X_{2} CH (NH X_{2}) COOH

Practice Structural Identification and Practical Organic Chemistry More on Structure determination from reaction sequences

Previous questionNext question

Methanal is treated with CHX3​CHX2​MgBr followed by HX3​OX+ to give A. A reacts with PBrX3​ to give B, B with KCN to give C, and C is hydrolysed with aqueous acid to give D. D is treated with BrX2​ and a trace of red phosphorus and then with excess NHX3​ to give E. E is

Answer: A

More questions on Structure determination from reaction sequences