The major product formed in the following reaction is
F3 Vinanti Teaching 29.05.23 D135
F3 Vinanti Teaching 29.05.23 D136

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CSIR-UGC (NET) Chemical Science: Held on (15 Dec 2019)
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  1. F3 Vinanti Teaching 29.05.23 D137
  2. F3 Vinanti Teaching 29.05.23 D138
  3. F3 Vinanti Teaching 29.05.23 D139
  4. F3 Vinanti Teaching 29.05.23 D140

Answer (Detailed Solution Below)

Option 4 : F3 Vinanti Teaching 29.05.23 D140
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Detailed Solution

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Concept:

Cbz(carboxy benzyl)-Protecting group:

  • It is used to protect amine group. 
  • It is synthesized by the reaction of benzyl chloroformate (BnOCOCl) with any weak base.
  • Cbz makes -NH2 group less nucleophilic as the loan pair electrons present on the amine group are in conjugation with the carbonyl group.
  • Example
    F3 Vinanti Teaching 29.05.23 D141
  • Deprotection of amine group or removal of Cbz-group occurs with the help of strong acid like HBr/AcOH or in the presence of H2/Pd.
  • Example:

F1 Savita Teaching 29-5-23 D38

t-butyl ester: (CO2t-Bu)

  • When carboxylic acids react with isobutene in presence of acid, it gives t-butyl ester.
  • Example:  F1 Savita Teaching 29-5-23 D36
    F1 Savita Teaching 29-5-23 D37
  • It is used in the protection of carboxylic acid group(-COOH).
  • t-Bu ester being a bulky one doesn't favour nucleophilic attack to which it doesn't undergo base hydrolysis rather they prefer acid hydrolysis.
  • Example:F1 Savita Teaching 29-5-23 D35

Explanation:

The mechanism of the reaction as follows:

F1 Savita Teaching 29-5-23 D34

Conclusion:

Therefore the correct answer is option (4).

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