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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

Dimethylamine(CH3) 2 NHhas a molecular weight of 45 and a boiling point of 7.40C. Trimethylamine, (CH3) 3N, has a higher molecular weight (59) but a lower boiling point(3.50C) . Explain this apparent discrepancy.

Question: Suppose you have just synthesized heptanoic acid from heptan-1-ol. The product is contaminated by sodium dichromate, sulfuric acid, heptan-1-ol, and possibly heptanal. Explain how you would use acid-base extractions to purify the heptanoic acid. Use a chart, like that in Figure 20-3, to show where the impurities are at each stage.

Predict the productsand propose mechanisms for the following reactions.

Question: Oxidation of primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

  1. Show how you would use acid-base extraction to purify the pentanal.
  2. Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

Question:

  1. The Key Mechanism for Fischer esterification omitted some important resonance forms of the intermediates shown in brackets. Complete the mechanism by drawing all the resonance forms of these two intermediates.
  2. Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
  3. The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.
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