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Chapter 20: Q20P. (page 1067)

Question: Propose a mechanism for conversion of the dianion to the ketone under mildly acidic conditions.

Short Answer

Expert verified

The mechanism for converting dianion to ketone is as follows:

Step by step solution

01

Dianion to ketone conversion

A dianion compound with two negative charges, when treated under mildly acidic conditions, converts into a hydrate of the ketone.A ketone is formed when water is cleaved from a hydrate of the ketone.

02

Conversion of dianion to ketone

A ketone hydrate is formed on treating dianion with two equivalents of acids. Again when treated with acid, water is removed, and a secondary cation is formed. On treating this secondary cation with water, a ketone product is formed.

Mechanism for the conversion of dianion to ketone

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Most popular questions from this chapter

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

(b) methyl formate (bp 32°C)

(c) ethyl phenylacetate

Question: What do the following pKa values tell you about the electron-withdrawing abilities of nitro, cyano, chloro, and hydroxy groups?

Question: Convert the following infrared wavenumbers into wavelengths.

(a) 1600 cm-1, typical for an aromatic

(b) 3000 cm-1 , typical for a saturated C-H bond

(c) 1715 cm-1 , typical for a ketone carbonyl

(d) 1750cm-1 , typical for an ester carbonyl

(e)2200cm-1 , typical for a nitrile

(f) 3300cm-1 , typical for an alcohol O-H.

Question: Predict the products (if any) of the following acid-base reactions.

  1. formic acid + ammonia
  2. terphthalic acid + excess NaOH
  3. p-toluic acid + sodium trifluoroacetate
  4. α-chloropropionic acid + sodium propionate
  5. benzoic acid + potassium phenoxide

The reaction of tert-butyl alcohol with concentrated HCl goes by the SN1 mechanism. Write a mechanism for this reaction.
See all solutions

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