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Chapter 21: Q.32P.b (page 1123)
Show how you would use anhydrides to synthesize the following compounds. In each
case, explain why an anhydride might be preferable to an acid chloride.
(b) n-octyl acetate
Answer
The use of anhydride to synthesize the given compound is given below.
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Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
d.Ph2CHOH
(a)Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize
(i) benzyl acetate and
(ii) N,N-diethylacetamide.
(b)Propose a mechanism for each synthesis in part (a).
An unknown compound of the molecular formula C5H9NO gives the IR and NMR spectra shown here. The broad NMR peak at d 7.55 disappears when the sample is shaken with D2O . Propose a structure, and show how it is consistent with the absorptions in the spectra.
The IR spectra shown next may include a carboxylic acid, an ester, an amide, a nitrile, an acid chloride, or an acid anhydride.
Determine the functional group suggested by each spectrum, and list the specific frequencies you used to make your decision.
Show how you would use anhydrides to synthesize the following compounds. In eachcase, explain why an anhydride might be preferable to an acid chloride.
(a) n-octylformate
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