Chapter 20: Q79 (page 816)
Reaction of benzyl magnesium chloride with formaldehyde yields alcohols N and P after protonation. Draw a stepwise mechanism that shows how both products are formed.

Short Answer

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Chapter 20: Q79 (page 816)
Reaction of benzyl magnesium chloride with formaldehyde yields alcohols N and P after protonation. Draw a stepwise mechanism that shows how both products are formed.


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Synthesize each compound from cyclohexanol, ethanol, and any other needed reagents.
a.

b.

c.

d.

e.

Synthesize each compound from the given starting material. You may use any other required inorganic reagents.

Treatment of compound C (molecular formula ) with , followed by H2O, affords compound D (molecular formula ). Compound D has a strong peak in its IR spectrum at 3600–3200 . The NMR spectral data of C and D are given. What are the structures of C and D?Compound C signals at 1.3 (singlet, 6 H) and 2.4 (singlet, 2 H) ppm Compound D signals at 1.2 (singlet, 6 H), 1.6 (singlet, 1 H), 2.7 (singlet, 2 H), and 7.2 (multiplet, 5 H) ppm
What ester and Grignard reagent are needed to synthesize each alcohol?
a.

b.

Lithium tri-sec-butylborohydride, also known as L-selectride, is a metal hydride reagent that contains three sec-butyl groups bonded to boron. When this reagent is used to reduce cyclic ketones, one stereoisomer often predominates as product. Explain why the reduction of 4-tert-butylcyclohexanone with L-selectride forms the cis alcohol as the major product.

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