Chemistry Homework Solutions

Aldol Condensation

In an aldol condensation, why might it be essential that the benzaldehyde contain no benzoic acid?

Grignard Reagents

It is likely that the amount of Grignard reagent indicated in an analysis is greater than the amount of Grignard reagent actually present just before water was added. Explain.

What hydrocarbons would you expect?

What hydrocarbon would you expect to obtain by the action of water on each of the Grignard reagents listed below? (a) Butylmagnesium bromide (b) sec-Butylmagnesium bromide (c) iso-Butylmagnesium bromide (d) tert-Butylmagnesium bromide

Predict the products

What product would each of the following Grignard reagents yield when treated with D2O? (a) Butylmagnesium bromide (b) sec-Butylmagnesium bromide (c) iso-Butylmagnesium bromide (d) tert-Butylmagnesium bromide

Simple dissociation

The dissociation pK for acetic acid is 4.76. Suppose that we dissolve a mole of this weak acid in 10L of water. Find the pH of the resulting solution. What fraction of acetic acid molecules dissociated?

C=C stretching mode

Explain why the C=C stretching mode gives rise to a rather weak IR band in 1-methylcyclohexane, while in its isomer, methylenecyclohexene, the band is of medium to strong intensity.

Propyl p-tolyl ether

There are only four lines in the aromatic region of the fully 1H decoupled 13C NMR spectrum of propyl p-tolyl ether (110-160 ppm), yet there are six aromatic carbon atoms. Explain.

Acidic Species

Predict which of the following species is the most acidic. Explain. (A) Phthalimide (B) Benzamide

N-Phenylmaleimide

N-Phenylmaleimide can act as a dienophile in the Diels-Alder reaction. Draw the structure of the product that would be formed by the treatment of N-phenylmaleimide with (a) 3-sulfolene and (b) furan.

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