Question
Asked Mar 4, 2020
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What α-halo carbonyl compound is needed to synthesize each amino acid: (a) glycine; (b) isoleucine; (c) phenylalanine?

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Expert Answer

Step 1

(a)The alpha-halo carbonyl compound needed to synthesize glycine must have same number of carbon atoms as in glycine. The alpha-halo carbonyl compound undergoes SN2 reaction with ammonia to form an amino acid. The corresponding chemical reaction is shown below:

The alpha-halo carbonyl compound needed to synthesize glycine is 2-bromoacetic acid.

Chemistry homework question answer, step 1, image 1

Step 2

(b) The alpha-halo carbonyl compound needed to synthesize isoleucine must have same number of carbon atoms. The alpha-halo carbonyl compound undergoes SN2 reaction with ammonia to form an amino acid. Since SN2 reaction gives inversion of configuration at the reaction center, the center containing halogen must have opposite configuration as that of center containing amino group. The corresponding chemical re...

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