The structure of the compound A in the following reaction sequence is
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CSIR-UGC (NET) Chemical Science: Held on (18 Sept 2022)
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  1. F3 Vinanti Teaching 29.08.23 D30
  2. F3 Vinanti Teaching 29.08.23 D31
  3. F3 Vinanti Teaching 29.08.23 D32
  4. F3 Vinanti Teaching 29.08.23 D33

Answer (Detailed Solution Below)

Option 4 : F3 Vinanti Teaching 29.08.23 D33
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Concept:

LiBH4 is a mild and selective reducing agent, making it suitable for a wide range of functional group reductions. It is less reactive towards other functional groups than some harsher reducing agents, allowing for greater control over reactions. Some common functional groups that can be reduced by LiBH4 include carbonyl compounds (aldehydes and ketones), carboxylic acids and their derivatives, and imines.

Explanation:

  • LiBH4 is less reactive and not enough to reduce amide, it can only reduce aldehyde, ketone to its corresponding alcohol. 
  • t-butyl is a bulky group so LiBH4 is unable to reduce the group.

F3 Vinanti Teaching 29.08.23 D34

  • After the formation of diol cyclization occurs in the presence of CF3CO2H and H2O. 

F3 Vinanti Teaching 29.08.23 D35

Conclusion:

Hence, the intermediate A formed is cis-diol.

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