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Problem 22-2
(a) 4 (b) 3 (c) 3 (d) 2 (e) 4 (f) 5
Problem 22-4
Acid-catalyzed formation of an enol is followed by deuteronation of the enol double bond and dedeuteronation of oxygen.
Problem 22-5
1. Br2; 2. Pyridine, heat
Problem 22-6
The intermediate α-bromo acid bromide undergoes a nucleophilic acyl substitution reaction with methanol to give an α-bromo ester.
Problem 22-7
Problem 22-9
Acid is regenerated, but base is used stoichiometrically.
Problem 22-10
1. Na+ −OEt; 2. PhCH2Br; 3. H3O+
1. Na+ −OEt; 2. CH3CH2CH2Br; 3. Na+ −OEt; 4. CH3Br; 5. H3O+
1. Na+ −OEt; 2. (CH3)2CHCH2Br; 3. H3O+
Problem 22-11
Malonic ester has only two acidic hydrogens to be replaced.
Problem 22-12
1. Na+ −OEt; 2. (CH3)2CHCH2Br; 3. Na+ −OEt; 4. CH3Br; 5. H3O+
Problem 22-13
Problem 22-14
None can be prepared.
Problem 22-15
1. 2 Na+ −OEt; 2. BrCH2CH2CH2CH2Br; 3. H3O+
Problem 22-16
Alkylate phenylacetone with CH3I
Alkylate pentanenitrile with CH3CH2I
Alkylate cyclohexanone with H2C CHCH2Br
Alkylate cyclohexanone with excess CH3I
Alkylate C6H5COCH2CH3 with CH3I
Alkylate methyl 3-methylbutanoate with CH3CH2I
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