Chapter 18: Q42P (page 967)
Sketch the expected proton NMR spectrum of 3,3-dimethylbutanal.
Short Answer
The expected proton NMR spectrum of 3,3-dimethylbutanal is as follows:

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Chapter 18: Q42P (page 967)
Sketch the expected proton NMR spectrum of 3,3-dimethylbutanal.
The expected proton NMR spectrum of 3,3-dimethylbutanal is as follows:

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Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(j) (k) (l)
Question. The mass spectrum of unknown compound A shows a molecular ion at m/z 116 and prominent peaks at m/z 87 and m/z 101. Its UV spectrum shows no maximum above 200 nm. The IR and NMR spectra of A follow. When A is washed with dilute aqueous acid, extracted into dichloromethane , and the solvent evaporated, it gives a product B. B shows a strong carbonyl signal at 1715 cm-1in the IR spectrum and a weak maximum at 274nm(E =16) in the UV spectrum. The mass spectrum of B shows a molecular ion of m/z 72. Determine the structures of A and B, and show the fragmentation to account for the peaks at m/z 87 and 101.


In the mechanism for acetal hydrolysis shown, the ring oxygen atom was protonated first, the ring was cleaved, and then the methoxy group was lost. The mechanism could also be written to show the methoxy oxygen protonating and cleaving first, followed by ring cleavage. Draw the alternative mechanism.
PROBLEM 18-10
Predict the products of the following reactions:

Within each set of structures, indicate which will react fastest, and which slowest, toward nucleophilic addition in basic conditions.
(a)

(b)

(c)

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