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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 纬 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 纬 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 纬 hydrogen in butan-2-one, so no products were observed in the McLafferty rearrangement.

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Most popular questions from this chapter

Rank the following carbonyl compounds in order of increasing equilibrium constant for hydration:

CH3COCH2Br BrCH2CHO鈥�鈥�鈥�鈥�鈥�鈥�CH2O鈥�鈥�鈥�鈥�鈥�鈥�CH3COCH3鈥�鈥�鈥�鈥�鈥�鈥�CH3CHO

PROBLEM 18-10

Predict the products of the following reactions:

Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.

(a)CH3CO(CH2)4CH3 (b)CH3(CH2)2CO(CH2)2CH3 (c)CH3(CH2)CO(CH2)2CH3

(d)PhCOPh (e)CH3CH2CH2CHO (f)CH3COCH3

(g)CH3CH2CHBrCH2CH(CH3)CHO (h)Ph-CH=CH-CHO

(i)CH3CH=CH-CH=CH-CHO

(j) (k) (l)

Show how would you accomplish the following syntheses. You may use whatever additional reagents you need.

(a)

(b)

(c)

(d)

(e)

(f)

(a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:

(b) The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.
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