Chapter 17: Q9P (page 533)
Show the products obtained from addition of methylmagnesium bromide to the following compounds:
- Cyclopentanone
- Benzophenone (diphenyl ketone)
- 3-Hexanone
Short Answer
a.

b.

c.

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Chapter 17: Q9P (page 533)
Show the products obtained from addition of methylmagnesium bromide to the following compounds:
a.

b.

c.

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Benzoquinone is an excellent dienophile in the Diels – Alder reaction. What product would you expect from reaction of benzoquinone with 1 equivalent of 1,3 butadiene? From reaction with 2 equivalents of 1,3 butadiene?
Rank the following substances in order of increasing acidity:
Propose a structure consistent with the following spectral data for a
compound :
IR:
NMR: (12 H, singlet); (4 H, singlet); (2 H, singlet)
Compound A, , undergoes reaction with dilute at to yield a mixture of two alkenes, . The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Write the reactions involved, and identify A and B.
Question:The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base:
(a) tert-butyldimethylsilyl chloride (TBS-Cl)
(b) triisopropylsilyl chloride (TIPS-Cl)
(c) triethylsilyl chloride (TES-Cl)
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