Chapter 21: Q5P (page 1094)
For each set of IR and NMR spectra, determine the structure of the unknown compound. Explain how your proposed structure fits the spectra.
(a) C3H5NO


(b) C5H8O2

Short Answer
(a)

(b)

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Chapter 21: Q5P (page 1094)
For each set of IR and NMR spectra, determine the structure of the unknown compound. Explain how your proposed structure fits the spectra.
(a) C3H5NO


(b) C5H8O2

(a)

(b)

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(a)Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.
(b) Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.
(c)Propose a secondmechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the otheroxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.
(d)Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.
(e)Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an reaction?
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.
(c) phthalic acid monoamide
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).
Propose a mechanism for the following ring-opening transesterification. Use the mechanism in Problem 21-13 as a model.
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