Chapter 13 Aldehydes and Ketones
Multiple Choice
Section: 13.1
Difficulty Level: Medium
1. How many chiral ketones are there that have the molecular formula C 6H12O?
a)
b)
c)
d)
1
2
4
6
Section: 13.1
Difficulty Level: Medium
2. How many achiral ketones are there that have the molecular formula C6H12O?
a)
b)
c)
d)
3
4
5
6
Section: 13.1
Difficulty Level: Hard
3. How many chiral aldehydes are there that have the molecular formula C 6H12O?
a)
b)
c)
d)
2
3
4
5
Section: 13.1
Difficulty Level: Hard
4. How many achiral aldehydes are there that have the molecular formula C6H12O?
a)
b)
c)
d)
4
5
6
7
264
Chapter 13 Aldehydes and Ketones
Section: 13.2
Difficulty Level: Easy
5. Which compounds are named correctly?
OH
CH3
O
O
CH
CH
HO O
CH3CHCOH
o-hydroxybenzaldehyde
I
2-hydroxypropanoic acid
III
2-methylbenzaldehyde
II
H
O
O
O
C
C
C O
CCH3
CH3CCH2CH
H
CH3
1,3-butanedione
IV
a)
b)
c)
d)
benzophenone
V
cinnamaldehyde
VI
I, II, III
IV, V, VI
II, IV, V
III, IV, VI
Section: 13.2
Difficulty Level: Easy
6. Which is the correct structure for 2-hydroxybenzophenone?
OH
a)
O
CH3CH
O
CH
b)
C
OH
O
O
c)
C
CH3
CH
d)
OH
OH
a) a
b) b
c) c
d) d
265
Chapter 13 Aldehydes and Ketones
Section: 13.3
Difficulty Level: Medium
7. Arrange the compounds in order of increasing solubility in water (least first).
O
CH
O
O
I
a)
b)
c)
d)
CH3CH2CH
II
O
H3C
CHCH2CH2CH2CH2CCH3
H3C
III
IV
I, II, III, IV
IV, I, II, III
IV, III, II, I
II, II, I, IV
Section: 13.3
Difficulty Level: Medium
8. Arrange the compounds in order of increasing solubility in water (least first) (hint: add the lone pairs,
molecule polarity and the ability to accept/donate hydrogen bonds)
O
OH
O
CH3CH2CH2CH
CH3CH2CH2CH2
CH3CH2CH2CH2CH3
I
II
III
a)
b)
c)
d)
CH3CH2
CH2CH3
IV
II, I, IV, III
I, II, IV, III
III, IV, I, II
II, I, III, IV
Section: 13.3
Difficulty Level: Medium
9. Arrange the compounds in order of increasing boiling point (lowest first). (hint: add the lone pairs,
molecule polarity and the ability to accept/donate hydrogen bonds)
O
OH
O
CH3CH2CH2CH
CH3CH2CH2CH2
CH3CH2CH2CH2CH3
I
II
III
a) II, I, IV, III
b) I, II, IV, III
c) IV, III, I, II
d) II, I, III, IV
266
CH3CH2
CH2CH3
IV
Chapter 13 Aldehydes and Ketones
Section: 13.3
Difficulty Level: Medium
10. Arrange the compounds in order of increasing boiling point (lowest first).
O
CH
O
I
a)
b)
c)
d)
CHCH2CH2CH2CH2CCH3
CH3CH2CH
II
O
H3C
O
H3C
III
IV
III, II, IV, I
IV, I, II, III
IV, III, II, I
II, II, I, IV
Section: 13.5
Difficulty Level: Medium
11. A Grignard reagent is prepared by reacting cyclopentanol with first thionyl chloride and then
magnesium in ether. The Grignard reagent is then reacted with acetaldehyde (ethanal) and the reaction
mixture acidified. What is the major final product of this series of reactions?
OH
CHCH3
a)
OH
b)
CH2CH2OH
c)
d)
CH2CH3
a)
b)
c)
d)
a
b
c
d
Section: 13.5
Difficulty Level: Medium
12. Which is the major product of the reaction of ethyl Grignard and propiophenone (ethyl phenyl ketone)?
CH2CH3
a)
c)
CCH2CH3
CH2CH3
b)
CCH3
OH
OH
CH3
CH3
CCH2CH3
CCH3
d)
OH
OH
a) a
b) b
c) c
d) d
Section: 13.5
Difficulty Level: Medium
13. Which reaction does not lead to 3-methyl-3-hexanol?
267
CH2OCH3
Chapter 13 Aldehydes and Ketones
a)
b)
c)
d)
2-butanone + propylmagnesium bromide
3-hexanone + methyl magnesium bromide
2-pentanone + ethylmagnesium bromide
3-pentanone + ethylmagnesium bromide
Section: 13.5
Difficulty Level: Medium
14. Which is the major product of the following reaction?
O
ether
CCH3 + CH3MgBr
OH
a)
CCH3
H3O
OH
b)
CH2CHCH3
CH3
OH
CHCH2OH d)
c)
CHCH2CH3
CH3
a) a
b) b
c) c
d) d
Section: 13.5
Difficulty Level: Hard
15. Which is the major product of the following reaction?
MgBr +
a)
D
b)
CH3CH2ND2
H
a) a
b) b
c) c
d) d
Section: 13.6
Difficulty Level: Easy
16. Which compounds are acetals?
268
ether
c)
ND2
d)
NDCH2CH3
Chapter 13 Aldehydes and Ketones
NH2
N
N
O
-O
P
O
N
NH
N
N
O
O
O
O-
H
H
-O
H
OH
H
P
O
O
O-
H
H
I
H
H
OH
H
O
N
O
P O
NH2
NH
N
N
NH2
O
OH
H
H
OH
H
OH
N
O
-O
P O
O
O
OH
III
a)
b)
c)
d)
H
II
N
-O
O
H
H
OH
H
OH
IV
I, II, III
II, III. IV
I, II, III, IV
II, IV
Section: 13.6
Difficulty Level: Medium
17. Which is the product of the following reaction?
O
O
H3O
H2O
O
a) CH3CH2CH +
O
O
b) HOCH2CH2CH2OH + HCH
CH3OH
O
O
c) CH3CCH2CH2CH2CH
O
d) HCCH2CH + CH3OH
a) a
b) b
c) c
d) d
Section: 13.6
Difficulty Level: Medium
18. Which compound reacts with aqueous acid to give an aldehyde?
269
Chapter 13 Aldehydes and Ketones
O
HO
H3C
O
a)
b)
OCH3
CH3
O
CH3
O
c)
d)
OCH3
a) a
b) b
c) c
d) d
Section: 13.6
Difficulty Level: Medium
19. Which compounds are acetals?
CH3
O
O
OH
O
II
I
O
O
III
CH3
O
CH3
CH3
a)
b)
c)
d)
OCH3
O
O
O
IV
V
VI
I, II, III
IV, V, VI
III, IV, VI
II, IV, V
270
CH3
Chapter 13 Aldehydes and Ketones
Section: 13.6
Difficulty Level: Hard
20. 1-Hexene was treated with dilute sulfuric acid. The product of that reaction was reacted with
potassium dichromate in sulfuric acid. This product was then treated with methanol in hydrochloric acid.
What is the major product of this series of reactions?
OCH3
a) CH3CH2CH2CH2CH2CH
OCH3
b) CH3CH2CH2CH2CCH3
OCH3
OCH3
O
O
c) CH3CH2CH2CH2CH2COCH3 d) CH3CH2CH2CH2CH2CCH3
a) a
b) b
c) c
d) d
Section: 13.7
Difficulty Level: Medium
21. Which is the major product of the reaction of cyclopentylamine and benzaldehyde followed by nickel
and hydrogen?
a)
CH2NH
b)
NH
c)
NHCH2
d)
CH2NHCH2
a) a
b) b
c) c
d) d
271
Chapter 13 Aldehydes and Ketones
Section: 13.7
Difficulty Level: Medium
22. The following product can be made from the reductive amination of which combination of
compounds?
NH2
CH
a)
b)
c)
d)
benzaldehyde and benzylamine
benzaldehyde and aniline
benzophenone and ammonia
acetophenone and ammonia
Section: 13.7
Difficulty Level: Medium
23.
The following product can be made from the reductive amination of which combination of
compounds?
HN
a)
b)
c)
d)
benzaldehyde and benzylamine
benzaldehyde and aniline
benzophenone and ammonia
acetophenone and ammonia
272
Chapter 13 Aldehydes and Ketones
Section: 13.7
Difficulty Level: Medium
24. Which is the best procedure for the following preparation?
O
N
HN
a)
HN
NaBH4
H2O
NaBH4
H2O
b)
HN
HN
c)
d)
Ni / H2
Ni / H2
a) a
b) b
c) c
d) d
Section: 13.7
Difficulty Level: Medium
25. Which compound is a Schiff base?
a)
NH2
b) H2N N
c) CH3CH2NH3 CH3
a) a
b) b
c) c
d) d
273
d)
NH
Chapter 13 Aldehydes and Ketones
Section: 13.5 and 13.7
Difficulty Level: Medium
26. Which is the product of the following sequence of reactions?
H2N
O
H2N
O
H
H2 / Pt
ethanol
N
HN
N
HN
HN
NH
III
a)
b)
c)
d)
NH
II
I
HN
IV
I
II
III
IV
274
Chapter 13 Aldehydes and Ketones
Section: 13.5 and 13.7
Difficulty Level: Hard
27. Benzaldehyde reacts according to the following reaction sequence. What final product is formed?
(Hint: As shown in chapter 9, benzylic positions can be easily oxidized.)
NH2
Br
+ Mg
K2Cr2O7
O
H
NH2
ethanol
H2SO4
diethyl ether
O
OH
O
OH
II
I
N
N
N
N
III
a)
b)
c)
d)
IV
I
II
III
IV
275
Chapter 13 Aldehydes and Ketones
Section: 13.8
Difficulty Level: Medium
28. Which structure is the major tautomer of 2-pentanone in aqueous acid?
OH
OH
a)
OH
b)
c)
a) a
b) b
c) c
d) d
Section: 13.8
Difficulty Level: Medium
29. Which structure is the major tautomer of 3-oxo-pentanoic acid in aqueous medium?
O
H+/H2O
OH
O
O
O
OH
OH
I
O
OH
OH
OH
II
OH
III
a) I
b) II
c) III
d) IV
276
OH
d)
Chapter 13 Aldehydes and Ketones
Section: 13.8
Difficulty Level: Hard
30. Which is the main product from the reaction of (S)-2-methylpentanal with an aqueous base?
O
H
NaOH/ethanol
(S)-2-methylpentanal
HO
HO
I
H
O
H
II
O
H
III
racemic-2-methylpentanal
a)
b)
c)
d)
H
IV
(R)-2-methylpentanal
I
II
III
IV
277
Chapter 13 Aldehydes and Ketones
Section: 13.5 and 13.9
Difficulty Level: Medium
31. Which is the product of the following sequence of reactions?
OH
O
OH
HO
H2SO4/H2O
Na2Cr2O7
H2SO4
O
H2O
work-up
O
O
O
OH
O
II
I
O
O
O
O
O
IV
III
a)
b)
c)
d)
I
II
III
IV
278
OH
Chapter 13 Aldehydes and Ketones
Section: 13.5 and 13.9
Difficulty Level: Medium
32. Which is the product of the following sequence of reactions?
OH
O
OH
HO
H2SO4/H2O
O
Na2Cr2O7
H2SO4
H2O
work-up
O
O
O
OH
O
II
I
H
O
O
O
OH
III O
a)
b)
c)
d)
O
IV
OH
I
II
III
IV
279
Chapter 13 Aldehydes and Ketones
Section: 13.5 and 13.9
Difficulty Level: Medium
33. Which is the product of the following sequence of reactions?
OH
O
OH
HO
PCC
H2SO4/H2O
THF
O
O
O
O
I
O
II
H
H
O
O
O
OH
III O
a)
b)
c)
d)
O
IV
OH
I
II
III
IV
280
Chapter 13 Aldehydes and Ketones
Section: 13.10
Difficulty Level: Medium
34. Which is the major product of the following reaction?
O
NaBH4
H
H2 O
OH
O
OH
II
I
O
OH
H
III
IV
a) I
b) II
c) III
d) IV
Section: 13.5 and 13.10
Difficulty Level: Hard
35. Which is the major product of the following reaction?
O
O
NaBH4
H2O
OH
OH
b)
a)
HO
OH
c)
Mg
ether
HCl
d)
a) a
b) b
c) c
d) d
281
Chapter 13 Aldehydes and Ketones
Section: 13.5, 13.9, 13.10
Difficulty Level: Hard
36. Which is the best procedure for the following preparation?
O
O
CH2CH
CH
a)
CH3MgBr
H2SO4
K2Cr2O7
H2SO4
b)
Ag(NH3)2
NH3/H2O
CH3MgBr
H2SO4
c)
NaBH4
H2O
HCl
d)
LiAlH4
H2O
HBr
NaBH4
H2O
Mg
ether
Mg
ether
H2CO
CO2
H3O+
a) a
b) b
c) c
d) d
282
PCC
Chapter 13 Aldehydes and Ketones
Section: 13.5, 13.9, 13.10
Difficulty Level: Hard
37. Which is the best procedure for the following preparation?
O
O
OH
H
a)
CH3MgBr
H2SO4
K2Cr2O7
H2SO4
b)
Ag(NH3)2
NH3/H2O
CH3MgBr
H2SO4
c)
NaBH4
H2O
HCl
d)
LiAlH4
H2O
HBr
NaBH4
H2O
Mg
ether
Mg
ether
H2CO
CO2
H3O+
a) a
b) b
c) c
d) d
283
PCC
Chapter 13 Aldehydes and Ketones
Section: 13.6, 13.9, 13.10
Difficulty Level: Hard
38. Geranial reacts according to the following reaction sequence. Which product is formed?
O
geranial
OH
H2 / Pt
HO
H2O
K2Cr2O7
H2SO4
H2SO4/H2O
work-up
OH
O
O
HO
I
O
OH
II
O
HO
H
HO
III
a)
b)
c)
d)
IV
I
II
III
IV
284
Chapter 13 Aldehydes and Ketones
Section: 13.19
Difficulty Level: Easy
39. Which oxidation conditions are used in the industrial transformation of cyclohexanone to adipic acid?
a) K2Cr2O7 / H2SO4
b) KMnO4
c) HNO3
d) AgNO3 / NH3
a) a
b) b
c) c
d) d
Fill in the Blank Questions
Section: 13.2
Difficulty Level: Medium
1. The IUPAC name of the following structure is ___________________________.
O
O
Br
Section: 13.2
Difficulty Level: Medium
2. The IUPAC name of the following structure is ___________________________.
O
O
Section: 13.5
Difficulty Level: Medium
3. The major product that completes the following reaction is,
O
1)
MgBr
, ether
H
2) H+, H2O
285
Chapter 13 Aldehydes and Ketones
Section: 13.5
Difficulty Level: Medium
4. The starting material that completes the following reaction is,
1)
MgBr
, ether
HO
2) H+, H2O
Section: 13.6
Difficulty Level: Medium
5. The starting material that completes the following reaction is,
OH
HO
O
H+
O
Section: 13.7
Difficulty Level: Easy
6. The reagents that complete the following reaction are,
O
N
Section: 13.7
Difficulty Level: Medium
7. The starting material that completes the following reaction is,
NH3
NH2
H2, Ni
286
Chapter 13 Aldehydes and Ketones
Section: 13.9
Difficulty Level: Medium
8. The reagents that complete the following reaction are,
O
O
H
OH
Section: 13.10
Difficulty Level: Medium
9. The major product that completes the following reaction is,
1) LiAlH4, ether
O
2) H2O
Section: 13.10
Difficulty Level: Medium
10. The reagents that complete the following reaction are,
O
OH
H
True-False Questions
Section:13.2
Difficulty Level: Easy
1. The name of the following compound is 3-cyclohexenone.
O
287
Chapter 13 Aldehydes and Ketones
Section: 13.2
Difficulty Level: Medium
2. The name of the following molecule is 1,5-cyclohexanecarbaldehyde.
O
H
Section: 13.3
Difficulty Level: Easy
3. The order of boiling points for the following functional groups, of similar molecular weights, is,
ether > aldehyde > alcohol > carboxylic acid
Section: 13.5
Difficulty Level: Medium
4. The product of the reaction of 2-hydroxybutanal with phenyl magnesium bromide is 1-phenyl-1,2butanediol.
Section: 13.6
Difficulty Level: Medium
5. Two ways to drive the acetal reaction to completion are to use excess alcohol and remove water
produced.
Section: 13.7
Difficulty Level: Easy
6. The product of the reaction of 2-butanone with ammonia is 2-butanimine.
Section: 13.7
Difficulty Level: Medium
7. The product of the reaction of 3-pentanone with ammonia, hydrogen, and nickel is 3-pentanamine.
Section: 13.8
Difficulty Level: Medium
8. The mechanism for the formation of the enol form of propanal under basic conditions (NaOH) is,
O
O
H
H
H
H
HO
Na
Na
288
+ H2O
Chapter 13 Aldehydes and Ketones
Section: 13.8
Difficulty Level: Medium
9. The enol form of cyclohexanone is,
OH
Section: 13.9
Difficulty Level: Easy
10. The product of the reaction of benzaldehyde with silver ammonium nitrate (Tollens’ reagent) is
benzoic acid.
289
Chapter 13 Aldehydes and Ketones
Answers
Multiple Choice
1. a
2. c
3. b
4. b
5. a
6. b
7. b
8. c
9. c boiling points: butanal: 74.8oC, butanol 117.7 oC, pentane: 36.1 oC, diethyl ether 34.6 oC
10. a boiling points: cyclohexanecarbaldehyde 162 oC, cyclopentanone 131.1 oC, propanal: 49.0 oC, 7methyloctan-2-one 143 oC
11. a
12. a
13. d
14. a
15. a
16. c
17. b
18. c
19. c
20. b
21. c
22. c
23. b
24. c
25. d
26. b
27. d
28. c
29. a
30. c
31. c
32. c
33. b
34. b
35. a
36. c
37. d
38. b
39. c
290
Chapter 13 Aldehydes and Ketones
Fill in the Blank Questions
1. R – 4-bromo-5-oxohexanal
2. E – 4-nonene-2,8-dione
3.
OH
H
4.
O
5.
O
H
6.
H2 N
7.
O
H
8. H2CrO4 or Ag(NH3)2+
291
Chapter 13 Aldehydes and Ketones
9.
OH
10. 1) NaBH4, ethanol 2) H2O
True-False Questions
1. T
2. F
3. T
4. F
5. T
6. T
7. T
8. F
9. F
10. T
292