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Which is the major product of the reaction below? Wittig Reaction

Which is the major product of the reaction below?

Which is the major product of the reaction below
Which is the major product of the reaction below

Solution:

This is a Wittig reaction since the reagent is (Ph)3P=CHR.

To predict the product, we replace the oxygen in the =O with the CHR group in the Wittig reagent.

This reaction occurs to both aldehydes and ketones. However, aldehydes are more reactive then ketones. That is why, it is the =O on the right side that will react (aldehyde versus ketone on the ring).

We can eliminate choices A and B. Choice C has the double bond in the wrong place. On the starting molecules, we have 3 carbons coming off of the ring followed by the double bond. In choice C, there are 4 carbons followed by the double bond. D is the correct answer.

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