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Chapter 21: Q24P (page 1002)

What amino acid is formed when the aldehyde used in the Strecker synthesis is

a. acetaldehyde? b. 2-methylbutanal? c. 3-methylbutanal?

Short Answer

Expert verified

In Strecker synthesis, an aldehyde reacts with ammonia to form an imine. A nucleophilic addition reaction with cyanide ion forms an intermediate, which, when hydrolyzed, forms the amino acid.

Step by step solution

01

Strecker synthesis

In Strecker synthesis, an aldehyde reacts with ammonia to form an imine. A nucleophilic addition reaction with cyanide ion forms an intermediate, which, when hydrolyzed, forms the amino acid.

02

Formation of respective amino acids

a)

Treatment of acetaldehyde with HCN produces the corresponding α-aminonitrile which upon hydrolysis produces alanine. The reaction is as follows:

b)

Treatment of 2-methyl butanal with HCN produces the corresponding -amino nitrile which upon hydrolysis produces isoleucine. The reaction is as follows:

c)

Treatment of 3-methyl butanal with HCN produces the corresponding α-aminonitrile which upon hydrolysis produces leucine. The reaction is as follows:

Formation of leucine (c)

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Most popular questions from this chapter

What amino acid is formed using the N-phthalimidomalonic ester synthesis when the following alkyl halides are used in the third step?

(a)

(b) CH3SCH2CH2Br

What aldehydes are formed when the following amino acids are treated with ninhydrin?

a. tyrosine b. leucine c. arginine

The aldonic acid of D-glucose forms a five-membered-ring lactone. Draw its structure.

Reaction of a polypeptide with carboxypeptidase A releases Met. The polypeptide undergoes partial hydrolysis to give the following peptides.

What is the sequence of the polypeptide?

1. Ser, Lys, Trp4. Leu, Glu, Ser 7. Glu, His 10. Glu, His, Val

2. Gly, His, Ala 5. Met, Ala, Gly8. Leu, Lys, Trp11. Trp, Leu, Glu

3. Glu, Val, Ser 6. Ser, Lys, Val 9. Lys, Ser 12. Ala, Met

Which is the more effective buffer at physiological pH, a solution of 0.1 M glycylglycine or a solution of 0.2 M glycine?
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