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Show how you would convert glycine to following derivatives. Show the structure of the product in each case.

(a) Glycine isopropyl ester

(b) N-benzoylglycine

(c) N-benzyloxycarbonylglycine

(d) Tert-butyloxycarbonylglycine

Short Answer

Expert verified

Glycine when treated with propan-2-ol under acidic medium gets converted to glycine isopropyl ester. In acidic medium both the nitrogen of the amino group and the hydroxyl moiety present in the carboxylic acid gets protonated. The hydroxyl group gets converted to water which acts as a leaving group.In next step, hydroxyl group of propan-2-ol acts as a nucleophile and attacks at the carbonyl carbon of carboxylic acid group because of which required product is obtained.

Formation of the required derivative of glycine

Step by step solution

01

Step-1. Explanation of part (a):

Glycine when treated with propan-2-ol under acidic medium gets converted to glycine isopropyl ester. In acidic medium both the nitrogen of the amino group and the hydroxyl moiety present in the carboxylic acid gets protonated. The hydroxyl group gets converted to water which acts as a leaving group.In next step, hydroxyl group of propan-2-ol acts as a nucleophile and attacks at the carbonyl carbon of carboxylic acid group because of which required product is obtained.

Formation of the required derivative of glycine

02

 Step-2. Explanation of part (b):

Glycine when treated with benzoyl chloride in the presence of pyridine gets converted to N-benzoylglycine. Amino group of glycine is nucleophilic in nature and attacks at the carbonyl carbon of benzoyl chloride due to which a peptide bond is formed and chloride ion acts as a leaving group. Pyridine acts as a base and helps in the neutralization of the charge of the amino group after peptide bond formation.

Formation of the required derivative of glycine

03

Step-3. Explanation of part (c):

Glycine when treated with benzyl carbonochloridate in the presence of base like triethylamine, gets converted to its derivative N-benzoyloxycarbonylglycine. Amino group of glycine is nucleophilic in nature and attacks at the carbonyl carbon of benzyl carbonochloridate due to which peptide bond is formed and chloride ion acts as a leaving group. Triethylamine acts as a base and helps in neutralisation of the charge of the amino group after peptide bond formation.

Formation of the required derivative of glycine

04

Step-4. Explanation of part (d):

Glycine when treated with di-tert-butyl dicarbonate gets converted to tertiary butyl oxycarbonylglycine. Amino group acts as a nucleophile in glycine and attacks at the carbonyl carbon of di-tert-butyl dicarbonate and -OCOOCMe3 eliminates as a leaving group due to which a peptide bond is formed and required product gets obtained.

Formation of the required derivative of glycine

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Most popular questions from this chapter

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(a)trans-1-²ú°ù´Ç³¾´Ç²ú³Ü³Ù-2-±ð²Ô±ð→trans-pent-3-enoic acid (two ways)

(b)hex-3-ene→propanoic acid

(c) but-2-enal→but-2-enoic acid

(d) hexanoic acid→hexanal

(e)

(f)

(g)

(h)

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

c)

Tributylin hydride (Bu3SnH)is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. You job is to develop a mechanism, using the following reaction as an example.

The following bond-dissociation enthalpies may be helpful:

(a) Propose initiation and propagation steps to account for this reaction.

(b) Calculate values of Δ±á for your proposed steps to show that they are energetically feasible. (Hint: A trace of Br2 and light suggests it’s there only as an initiator, to create Brradicals. Then decide which atom can be extracted most favorably from the starting materials by the Brradical. That should complete the initiation. Finally, decide what energetically favored propagation steps will accomplish the reaction).

(a) Give the products expected when acetic formic anhydride reacts with

(i) aniline and

(ii) benzyl alcohol

(b) Propose mechanisms for these reactions.

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.
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