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Chapter 18: Q3P. (page 923)

Why were no products from McLafferty rearrangement observed in the spectrum of butan-2-one?

Short Answer

Expert verified

Butan-2-one has no gamma γ hydrogen, so no products were present in the McLafferty rearrangement.

Step by step solution

01

McLaffertyRearrangement

The characteristic fragmentation of the molecular ion of a carbonyl compound (ketones and aldehydes) having at least one gamma γ hydrogen is known as the McLafferty rearrangement.

02

McLafferty Rearrangement Observed in the Spectrum of Butan-2-one

The structure of butan-2-one is shown below.

Since there is no gamma γ hydrogen in butan-2-one, so no products were observed in the McLafferty rearrangement.

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Most popular questions from this chapter

(a) Propose a mechanism for the acid-catalyzed reaction of cyclohexanone with ethylene glycol to give cyclohexanone ethylene acetal.

(b) Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone ethylene acetal.

(c) Compare the mechanisms you drew in parts (a) and (b). How similar are these mechanisms, comparing them in reverse order?

(d) Propose a mechanism for the acid-catalyzed hydrolysis of the acetal given in Problem 18-26(f).

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts and show why this mechanism does not work for the other one.

Sodium triacetoxyborohydride, NaBHOAc3, is a mild reducing agent that reduces aldehydes more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:

(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.

(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.

Show how you would synthesize the following derivatives from appropriate carbonyl compounds

Show how you would accomplish the following synthesis.

(a) Acetphenone→ acetophenone cyanohydrin

(b) Cyclopentancarbaldehyde→ 2-cyclopentyl-2-hydroxyacetic acid

(c) Hexan-1-ol →2-hydroxyheptanoic acid
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