Return to Contents Chapter 18: Enols and Enolates Ch 18 contents
Enol and Enolate Questions
Qu1: How many α-hydrogens are there in each of the following aldehydes and ketones ?
(a) (CH3)2C=O (b) CH3CHO (c) H2C=O
(d) PhCHO (e) 2-pentanone (f) 3-pentanone
Qu 2: For each of the following pairs of compounds, draw their enols tautomers and choose the one the compound that has the greater enol content.
Qu 3: Draw the stepwise curly arrow mechanism for the tautomerisation of propanone with (i) and acid catalyst, H3O+ and (ii) a base catalyst, HO-
Qu 4: What are the major products of the reactions of 1-phenylethanone (acetophenone) with each of the following:
(a) Bromine in acetic acid
(b) Iodine in sodium hydroxide solution
(c) (i) NaOH then (ii) add ethyl iodide
(d) Ethyl magnesium bromide followed by acidic work up
(e) NaOH and methanal 
(f) NaOH and benzaldehyde
Qu 5: What are the major products of the reactions of  2-cyclohexenone with each of the following:
(a) NH3 in water
(b) Ethanethiol
(c) Lithium diethylcuprate then acidic work-up
(d) Ethyl lithium then acidic work-up

Answers ?

© Dr. Ian Hunt, Department of Chemistry, University of Calgary