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Chapter 21: Q23P (page 1002)

What alkyl halide is used in the acetamidomalonic ester synthesis to prepare a. lysine? b. phenylalanine?

Short Answer

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Formation of phenylalanine

Step by step solution

01

Ester synthesis

α-Bromomalonic ester and potassium phthalimide undergo an SN2 reaction. A proton is easily removed from the a-carbon of N-phthalimidomalonic ester because it is flanked by two carbonyl groups. The resulting carbanion undergoes an SN2reaction with an alkyl halide.

02

Preparation of given amino acid

a)

4-Bromo-1-butanamine is used in the acetamido malonic ester syntheses to prepare lysine which is given as follows:

b)

Benzyl bromide is used in the acetamido malonic ester synthesis to prepare phenylalanine which is represented as follows:

Formation of phenylalanine (b)

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