Question

Which of the following is the requirement for the intramolecular Sn2 reaction (intramolecular William Ether Synthesis) to occur in your reaction? Group of answer choices Anti-periplanar The arrangement of the bromine and hydroxide does not matter. cis Z

Answer 1

Answer:

D. Anti-periplanar

Explanation:

In the second step of the intramolecular William Ether Synthesis mechanism (figure 1) we will have the attack of the negative charge of the oxygen to the carbon bond to the Br. At the same time the Br leaves, so a bond would be broken (the C-Br bond) and a bond would be formed (the C-O bond).

Now, this process can happen only if the attack and the leaving group has an anti configuration (figure 2). In an anti configuration the nucleophile and the leaving group would have opposite directions.