PROBLEM ASSIGNMENT SEMESTER: JANUARY-APRIL 2011

CMT556 (CARBONYL CHEMISTRY) CHAPTER 16: ALDEHYDES AND KETONES

1. Which compound in each of the following pairs listed has the higher boiling point? Draw the
structures in each pair and explain your answer without consulting tables.

a) Benzaldehyde or benzyl alcohol

b) Acetophenone or 2-phenylethanol
c) Pentanal or 1-pentanol

2. Show how you would synthesize propanal from each of the following:

a) 1-propanol b) propanoic acid (CH3CH2COOH)

3. Which reagents would you use to carry out each of the following reactions?

a) Benzene bromobenzene phenylmagnesium bromide

benzyl alcohol benzaldehyde

b) Benzoyl chloride acetophenone

c) 1-Phenylethanol acetophenone

d) C6H5CH2CN 2-phenylethanal

4. The reactions of aldehydes and ketones with LiAlH 4 and NaBH4 are nucleophilic additions to the
carbonyl group. What is the nucleophile in these reactions?

5. Write a detailed mechanism for the formation of the hemiacetal from benzaldehyde and
methanol in the presence of an acid catalyst.

6. An optically active compound, C6H12O, gives a positive test with 2,4-dinitrophenylhydrazine but a
negative test with Tollens’ reagent. What is the structure of the compound? (Please recall
experiment I on aldehydes and ketones where you tested the known compounds and unknown
with these two reagents)

7. Give structures for compounds A-E.

H2CrO4 CH3MgI HA
Cyclohexanol A (C6H10O) B (C7H14O)
acetone H3O+ heat
O3 Ag2O, OH-
C (C7H12) D (C7H12O2) E (C7H12O3)
Zn, AcOH H3O+