Chapter 22: Q77P-b (page 1206)
Propose mechanisms for the following reactions.

Short Answer
Mechanism followed as:

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Chapter 22: Q77P-b (page 1206)
Propose mechanisms for the following reactions.

Mechanism followed as:

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Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound.
a.

Question: Predict the products of these reaction sequences.
a.

Show how you would use the acetoacetic ester synthesis to make the following compounds

(A true story.) Chemistry lab students added an excess of ethyl magnesiumbromide to methyl furoate, expecting the Grignard reagent to add twice and form the tertiary alcohol. After water workup, they found that the product was a mixture of two compounds. One was the expected product having two ethyl groups, but the unexpected product had added three ethyl groups. Propose a mechanism to explain the formation of the unexpected product.

Propose a mechanism for the conjugate addition of a nucleophile (Nuc:-) to acrylonitrile (H2C=CHCN) and to nitroethylene. Use resonance forms to show how the cyano and nitro groups activate the double bond toward conjugate addition.
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