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Chapter 29: Q42P (page 1193)

Devise a synthesis of each amino acid from acetaldehyde (CH3CHO):

(a) Glycine;

(b) Alanine.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Amino acid

Amino acid plays a vital role in body functions such as tissue repairing, digesting food, and enzyme formation.It is a white crystalline solid that dissolves in water.

02

Synthesis of amino acid

(a) When acetaldehyde is treated with bromine followed by acetic acid, it gives acetyl bromide. Acetyl bromide is then treated withCrO3 followed by sulphuric acid, and it gives bromoacetic acid which on further treatment with excess of NH3forms glycine.

Formation of glycine

(b) When acetaldehyde is treated with ammonium chloride and sodium cyanide, followed by hydrolysis, alanine is formed.

Formation of alanine

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Most popular questions from this chapter

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson鈥檚 disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

Explain why the pKaof the -NH3+group of an 伪-amino acid is lower than the pKaof the ammonium ion derived from a 1鈭�amine (RNH3+). For example, thepKa of therole="math" localid="1648617659352" -NH3+ group of alanine is 9.87 but thepka ofCH3NH3+ is 10.63.

The enolate derived from diethyl acetamidomalonate is treated with each of the following alkyl halides. After hydrolysis and decarboxylation, what amino acid is formed?

(a)CH3I(b)(CH3)2CHCH2Cl(c)CH3CH2CH(CH3)Br

Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds.

a. Val鈥揋lu

b. Gly鈥揌is鈥揕eu

c. M鈥揂鈥揟鈥揟

L-thyroxine, a thyroid hormone and oral medication used to treat thyroid hormone deficiency, is an amino acid that does not exist in proteins. Draw the zwitterionic form of L-thyroxine.
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