Chapter 20: Q31P (page 1038)
(a) Give the products expected when acetic formic anhydride reacts with
(i) aniline and
(ii) benzyl alcohol
(b) Propose mechanisms for these reactions.
Short Answer
(a)


(b)


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Chapter 20: Q31P (page 1038)
(a) Give the products expected when acetic formic anhydride reacts with
(i) aniline and
(ii) benzyl alcohol
(b) Propose mechanisms for these reactions.
(a)


(b)


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Suggest how you would convert trans-4-methylcyclohexanol to
(a) trans-1-chloro-4-methylcyclohexane.
(b) cis-1-chloro-4-methylcyclohexane.
Question: What do the following pKa values tell you about the electron-withdrawing abilities of nitro, cyano, chloro, and hydroxy groups?

Substituent effects: resonance and induction.

(a)When the methoxy group is in the meta position inB, is the acid stronger or weaker than inA? Is the methoxy group in the meta position electron-donating or withdrawing?
(b)When the methoxy group is in the para position inC, is the acid stronger or weaker than inA? Is the methoxy group in the para position electron-donating or withdrawing?
(c)How can this apparent contradiction be explained? Which effect is stronger for methoxy?
(d)When the fluoro group is in the meta position inE, is the acid stronger or weaker than inD? Is the fluoro group in the meta position electron-donating or withdrawing?
(e)When the fluoro group is in the para position inF, is the acid stronger or weaker than inD? Is the fluoro group in the para position electron-donating or withdrawing?
(f)Compare the results of the fluoro group with those of the above methoxy group. What must be different about the relative strength of the resonance and inductive effects for fluoro compared with methoxy?
Question:
Question: Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(a)
(b)
(c )
(d)
(e)
(f)
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