JEE Advanced 2016 · Paper 2 · Chemistry Q36

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ChemistrySingle correct+3Question 36 of 54

Passage

PARAGRAPH 2

Treatment of compound O with $\ce{KMnO4/H+}$ gave P, which on heating with ammonia gave Q. The compound Q on treatment with $\ce{Br2/NaOH}$ produced R. On strong heating, Q gave S, which on further treatment with ethyl 2-bromopropanoate in the presence of KOH followed by acidification, gave a compound T.

Compound O: a benzene ring carrying two adjacent n-propyl side chains (1,2-dipropylbenzene).

The compound T is

glycine

alanine

valine

serine

Answer and worked solution

Official answer: B

Gabriel synthesis. S is phthalimide. With KOH it forms potassium phthalimide, which is alkylated by ethyl 2-bromopropanoate. Acid hydrolysis then releases
$\ce{CH3CH(NH2)COOH},$
which is alanine (T).

(B)

Topics:Amino acids and proteins Amines

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JEE Advanced 2016 · Paper 2, Chemistry question 36