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Chapter 20: Q-24-30P (page 1038)

Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.

Short Answer

Expert verified

Using the starting materials the standard amino acids can be prepared as fellows.

(a)

(b)

(c)

Step by step solution

01

Reduction followed by the bromination and amino acid formation.

At first the keto group is reduced by zinc mercury in HCl medium. Then addition of bromine and amino group produced the amino acid.

(a)

02

Bromination and amino group addition

At first the bromination on the carboxylic acid is done. Then the amino group is added to this compound. Thus the amino acid is formed.

(b)

(b)

03

Oxidation and amino acid formation

At first the oxidation of aldehyde produced the carboxylic acid. This carboxylic acid on bromination and amino group addition produced the amino acid.

(c)

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Most popular questions from this chapter

Show how you would accomplish the following multistep syntheses using the indicated starting material and any necessary reagents.

(a) hept-6-en-1-ol caprolactone

(b) methoxybenzenep-methoxybenzamide

(c)

(d)

Gallic acid Mescaline

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.

(a) meso-2,3-dibromo-2,3-dichlorobutane

(b) -2,3-dibromo-2,3-dichlorobutane

(c) (2R,3S)-2-bromo-3-chlorobutane

(d) (2R,3S)-2,3-dibromobutane

(e) (R,R)-2,3-dibromobutane

(f)

(g)

(h)

Given the structure of ascorbic acid (vitamin C):

(a) Is ascorbic acid a carboxylic acid?

(b) Compare the acid strength of ascorbic acid (pKa=4.71) with acetic acid.

(c) Predict which proton in ascorbic acid is the most acidic.

(d) Draw the form of ascorbic acid that is present in the body (aqueous solution, pH = 7.4).

Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(a) propiophenone from propionic acid (two ways, using alkylation of the acid and using Friedel-Crafts acylation)

(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acid

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.

  1. Hexan-2-amine
  2. 2-methylpiperidine
  3. N-ethylpiperidine

5.

6.
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