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Chapter 29: Q42. (page 1193)

Devise a synthesis of each amino acid from acetaldehyde:

(a) Glycine;

(b) Alanine.

Short Answer

Expert verified

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.

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 with CrO3followed by sulphuric acid, and it gives bromoacetic acid which on further treatment with excess of NH3forms glycine.

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

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Most popular questions from this chapter

Question: Identify A and B, isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{4}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\), from the given \({}^{\bf{1}}{\bf{H}}\)NMR data: Compound A exhibits signals at 1.75 (doublet, 3H,\({\bf{J = 6}}{\bf{.9 Hz}}\)) and 5.89 (quartet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 6}}{\bf{.9 Hz}}\)) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 1}}{\bf{.9 Hz}}\)), and 5.59 (doublet, \({}^{\bf{1}}{\bf{H}}\), \({\bf{J = 1}}{\bf{.9 Hz}}\)) ppm.

Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:

What α- halo carbonyl compoundis needed to synthesize each amino acid?

(a) Glycine

(b) Isoleucine

(c) Phenylalanine

Question: Propose a structure for a compound of molecular formula \({{\bf{C}}_{\bf{7}}}{{\bf{H}}_{{\bf{14}}}}{{\bf{O}}_{\bf{2}}}\) with an IR absorption at \({\bf{1740}}\;{\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\) and the following \({}^{\bf{1}}{\bf{H}}\) NMR data:

\(\begin{array}{*{20}{c}}{{\bf{Absorption}}}&{{\bf{ppm}}}&{{\bf{Relative}}\;{\bf{area}}}\\\hline{{\bf{singlet}}}&{{\bf{1}}{\bf{.2}}}&{\bf{9}}\\{{\bf{triplet}}}&{{\bf{1}}{\bf{.3}}}&{\bf{3}}\\{{\bf{quartet}}}&{{\bf{4}}{\bf{.1}}}&{\bf{2}}\end{array}\)

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
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