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Question

The major products E and F in the following reaction sequence are 

The correct answer is

The question involves a reaction sequence, and we need to determine the major products E and F.

Let's break down the reaction:

  1. The starting material is an aromatic aldehyde.

    First step: Reaction with the Wittig reagent (triphenylphosphonium ylide) generated from Br(CH2)4Br using NaH in THF:

    • The ylide attacks the carbonyl carbon of the aldehyde.
    • This forms an alkene, leading to product E. This is a typical Wittig reaction.
  2. Product E: An alkene without substitution on the new double bond.

  3. Second step: Epoxidation and rearrangement using m-CPBA (meta-chloroperoxybenzoic acid) followed by BF3.OEt2:

    • m-CPBA transforms the alkene into an epoxide.
    • BF3.OEt2 induces epoxide opening and rearrangement to give product F.
  4. Product F: The rearranged product, including a cyclized ether ring.

Therefore, the major products E and F correspond to the first option given in the choices.

This matches the correct answer shown in the options.

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Important Questions from Organic Synthesis

  1. For an unambiguous single step synthesis of the following target molecule (TM), the best bond disconnection in its retrosynthetic analysis is
     

  2. The major products X and Y formed in the following reaction sequences are

  3. For the following reaction, the possible product(s) is/are

  4. The reaction(s) that yield(s) X as the major product is (are) 

  5. Consider the following reaction sequence. The correct option(s) is (are)

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