Chapter 17: Q29E (page 567)
Reduction of 2-butanone with NaBH4yields 2-butanol. Is the product chiral? Is it optically active? Explain.
Short Answer
The reaction followed is shown below.:
Chapter 17: Q29E (page 567)
Reduction of 2-butanone with NaBH4yields 2-butanol. Is the product chiral? Is it optically active? Explain.
The reaction followed is shown below.:
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Benzyl chloride can be converted intobenzaldehyde by treatment with nitromethane and base. The reactioninvolves the initial conversion of nitromethane in to its anion, followed by SN2 reaction of the anion with benzyl chloride and subsequent E2 reaction. Write the mechanism in detail, using curved arrows to indicate the electron flow in each step.
Benzyl chloride Nitromethane anion Benzaldehyde
How would you prepare the following compounds from 1-phenylethanol?
More than one step may be required.
(a) Acetophenone
(b) Benzyl alcohol
(c) m-Bromobenzoic acid
(d) 2-Phenyl-2-propanol
Question:When the alcohol below is treated with and pyridine, the expected elimination product is formed. However, when the same alcohol is treated with , the elimination product is 1,2-dimethylcyclopentene. Propose a mechanism for each pathway to account for these differences.
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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