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aleksklad [387]
3 years ago
11

Predict the product of the following Wittig reaction. Be sure your answer accounts for stereochemistry, where appropriate. If mu

ltiple stereoisomers form, be sure to draw all products using appropriate wedges and dashes.
1. PPh3
5-iodo-1-phenyl-1-pentanone →
2. n- BuLi

Chemistry
1 answer:
natta225 [31]3 years ago
3 0

Answer:

Final product: cyclopent-1-en-1-ylbenzene

Explanation:

In this case, we have a <u>Wittig reaction</u>. The addition of PPh_3 and n-Buli will produce the "<u>Ylide compound"</u>. First, we will have an<u> Sn2 reaction</u> in which the iodide is replaced by triphenylphosphine. Then the base n-Buli will remove a hydrogen atom to form a double bond <u>(Ylide compound)</u>. Then the double bond will be delocalized to produce a <u>carbanion</u>. This carbanion, will attack the carbon in the <u>carbonyl group</u> generating a <u>negative charge</u> in the oxygen. Then the negative charge will attack the phosphorous atom to produce a <u>cyclic structure</u>. Finally, the cyclic structure is broken to produce the <u>alkene</u> (cyclopent-1-en-1-ylbenzene).

See figure 1

I hope it helps!

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