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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

Question:

  1. Determine the structure of the carboxylic acid whose proton NMR spectrum appears below.
  2. Draw the NMR spectrum you would expect from the corresponding aldehyde whose oxidation gives this carboxylic acid.
  3. Point out two distinctive differences in the spectra of the aldehyde and the acid.

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

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.

Question: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

c)
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