Predict the product of the following Wittig reaction. Be sure your answer accounts for stereochemistry, where appropriate. If multiple stereoisomers form, be sure to draw all products using appropriate wedges and dashes. 1. PPh3
5-iodo-1-phenyl-1-pentanone →
2. n- BuLi

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

Explanation:

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

See figure 1

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