Chapter 20: Q19P a. (page 1066)
Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.
(a)

(b)

(c)

Short Answer
(a)

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Chapter 20: Q19P a. (page 1066)
Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.
(a)

(b)

(c)

(a)

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Question: The IR spectrum of trans-oct-2-enoic acid is shown. Point out the spectral characteristics that allow you to tell that this is a carboxylic acid, and show which features lead you to conclude that the acid is unsaturated and conjugated.

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.
a)

b)

c)

Question: Draw the structures of the following compounds.
Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.


Dimethylamine(CH3) 2 NHhas a molecular weight of 45 and a boiling point of 7.40C. Trimethylamine, (CH3) 3N, has a higher molecular weight (59) but a lower boiling point(3.50C) . Explain this apparent discrepancy.
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