1.

Which of the following correctly describes the bond angle and hybridizations present in
formaldehyde?
A) C, sp2; O, sp3; HCO, ~120°
B) C, sp2; O, sp2; HCO, ~120°
C) C, sp2; O, sp2; HCO, ~109.5°
D) C, sp3; O, sp2; HCO, ~109.5°
E) C, sp3; O, sp3; HCO, ~109.5°

2. The positively polarized carbon atom of a carbonyl group acts as:

A) an electrophile and a Lewis base.
B) a nucleophile and a Lewis base.
C) an electrophile and a Lewis acid.
D) a nucleophile and a Lewis acid.
E) both a Lewis acid and a Lewis base.
3. The double bond between carbon and oxygen is similar to an alkene C C, except that
C=O is:
A) shorter and weaker.
B) shorter and stronger.
C) longer and weaker.
D) longer and stronger.
E) longer.
4. Another name for β-methoxybutyraldehyde is:
A) 2-methoxypropanal.
B) 3-methoxypropanal.
C) 2-methoxybutanal.
D) 3-methoxybutanal.
E) 2-methoxypentanal.

5.

What is the correct IUPAC name for the following compound?

A) 2-oxocyclohex-3-ene carbaldehyde
B) 5-formylcyclohex-2-enone
C) 2-formylcyclohex-5-enone
D) 3-oxocyclohex-4-enal
6. Which of the following represents the correct ranking in terms of increasing boiling
point?
A) n-butane < 1-butanol < diethyl ether < 2-butanone
B) n-butane < 2-butanone < diethyl ether < 1-butanol
C) 2-butanone < n-butane < diethyl ether < 1-butanol
D) n-butane < diethyl ether < 1-butanol < 2-butanone
E) n-butane < diethyl ether < 2-butanone < 1-butanol

7. Which of the following compounds is most soluble in water?

A) acetone
B) cyclohexanone
C) 2-butanone
D) 3-butanone
E) benzophenone

8. When a carbonyl is part of a conjugated π-network, the C O stretch:

A) has a higher frequency than in a nonconjugated system.
B) has a lower frequency than in a nonconjugated system.
C) always occurs at 1710 cm-1.
D) occurs around 2700 cm-1.
E) cannot be distinguished from the C O stretch in a nonconjugated system

9. What name is given to the linear polymer which contains many formaldehyde units?
A) trioxane
B) formalin
C) paraformaldehyde
D) polyacetaldehyde
E) polyalal

10. What reagent can be used to convert 2-methylbutan-1-ol into 2-methylbutanal?

A) LiAlH4
B) Na2Cr2O7
C) O3
D) KMnO4
E) PCC

11. What reagents can be used to convert 1-hexyne into 2-hexanone?

A) 1. Sia2BH; 2. H2O2, NaOH
B) Hg2+, H2SO4, H2O
C) 1. O3; 2. (CH3)2S
D) 1. CH3MgBr; 2. CO2
E) 1. H2, Ni; 2. Na2Cr2O7, H2SO4
12. Oxidation of a 1° alcohol with chromic acid results in the production of ________.
A) an ester
B) a ketone
C) an aldehyde
D) an ether
E) none of the above

13. Oxidation of a 2° alcohol with chromic acid results in the production of ________.
A) an ester
B) a ketone
C) an aldehyde
D) an ether
E) none of the above

14. Oxidation of a 1° alcohol with pyridinium chlorochromate results in the production of

________.
A) an ester
B) a ketone
C) an aldehyde
D) an ether
E) none of the above

15. Oxidation of a 3° alcohol with chromic acid results in the production of ________.
A) an ester
B) a ketone
C) an aldehyde
D) an ether
E) none of the above

16. Treatment of a nitrile with a Grignard reagent followed by hydrolysis results in

________.
A) an ester
B) a ketone
C) an aldehyde
D) an ether
E) an alcohol
17. Which of the following describes a synthesis of an aldehyde?
A) hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst
B) reaction of a primary alcohol with Na2Cr2O7
C) reaction of a ketone with ozone
D) treatment of an alkene with Sia2BH
E) none of the above

18. Which series of reactions described below, if any, will result in the formation of 2-
methylpentan-3-one starting with 1-propanol?
A) 1. (CH3)2CHMgBr/ diethyl ether
2. dilute H3O+
3. PCC
B) 1. Na2Cr2O7/H2SO4 and heat
2. SOCl2
3. 2 (CH3)2CHMgBr/ diethyl ether
4. H3O+
C) 1. Na2Cr2O7/H2SO4 and heat
2. (CH3)2CHMgBr/ diethyl ether
3. dilute H3O+
4. LiAlH4
D) 1. PCC
2. (CH3)2CHLi/ diethyl ether
3. dilute H3O+
4. Na2Cr2O7/H2SO4 and heat
E) none of the above

19. When the carbonyl group of a neutral ketone is protonated,:

A) the resulting species becomes more electrophilic.
B) the resulting species is activated toward nucleophilic attack.
C) subsequent nucleophilic attack on the resulting species is said to occur under acid-
catalyzed conditions.
D) the resulting species has a positive charge.
E) all of the above

20. Consider the equilibrium of each of the carbonyl compounds with HCN to produce
cyanohydrins. Which is the correct ranking of compounds in order of increasing Keq
for this equilibrium?
 A) H2CO < cyclohexanone < CH3CHO < 2-methylcyclohexanone
B) CH3CHO < 2-methylcyclohexanone < cyclohexanone < H2CO
C) cyclohexanone < 2-methylcyclohexanone < H2CO < CH3CHO
D) cyclohexanone < 2-methylcyclohexanone < CH3CHO < H2CO
E) 2-methylcyclohexanone < cyclohexanone < CH3CHO < H2CO

21.

The following compound has been found effective in treating pain and inflammation (J. Med.
Chem. 2007, 4222). Which sequence correctly ranks each carbonyl group in order of increasing
reactivity toward nucleophilic addition?
A) 1 < 2 < 3
B) 2 < 3 < 1
C) 3 < 1 < 2
D) 1 < 3 < 2
22. Rank the following compounds in order of their propensity to become a hydrate in
water (i.e., start with the least easy to hydrate: CH3COCH2CH3, H2CO, Cl3CCHO,
and CH3CH2CHOxxxxxxxx

23.

Which sequence ranks the following carbonyl compounds in order of increasing rate of
nucleophilic addition?
A) 2 < 3 < 1
B) 3 < 2 < 1
C) 2 < 1 < 3
D) 1 < 3 < 2
24. An ylide is a molecule that can be described as a:
A) carbanion bound to a negatively charged heteroatom.
B) carbocation bound to a positively charged heteroatom.
C) carbocation bound to a carbon radical.
D) carbocation bound to a diazonium ion.
E) carbanion bound to a positively charged heteroatom.
25. Which of the following is also known as a Schiff base?
A) an imine
B) a cyanohydrin
C) a hydrate
D) sodium hydroxide
E) an aldehyde

26.

What product will result from the reaction shown?

A) imine
B) amino acid
C) amino alcohol
D) hydrazine
E) hydroxylamine

27.

What product will result from the reaction shown?

A) acetal
B) hydrazine
C) ester
D) ylide
E) ketone

28. Acetals will react with ________.

A) H3O⊕
B) NaOCH3
C) PhLi
D) CH3CH2MgBr
E) NaBH4
 29.

What would be the product of the following reaction? screwdriver

30. Why do acetal-forming reactions that use ethylene glycol have more favorable
equilibrium constants than those using methanol?
A) Ethylene glycol reacts more rapidly.
B) They are more favorable on entropy grounds.
C) They are more favorable on enthalpy grounds.
D) Ethylene glycol is acidic and catalyzes the reaction.
E) The ethylene acetal can serve as a protecting group.

31.

Which series of reactions described below will result in the formation of compound A, starting
with compound B?
A) 1. HO-(CH2)2-OH /trace H3O+
2. DMSO (COCl2)/Et3N, CH2Cl2
3. MgBr-(CH2)2-CH3/diethyl ether
4. work-up with H3O+
B) 1. PCC
2. SOCl2
3. LiCu-((CH2)2-CH3)2
4. work-up with H3O+
C) 1. Na2Cr2O7/H2SO4
2. SOCl2
3. 2 MgBr-(CH2)2-CH3/diethyl ether
4. work-up with H3O+
D) both A and B
E) both B and C
 32. What intermediate occurs when a ketone undergoes a Wolff-Kishner reduction?
A) a cyanohydrin
B) a hydrated aldehyde
C) a carboxylate
D) a semicarbazone
E) a hydrazine

33. The reagent which converts a carbonyl group of a ketone into a methylene group is
________.
A) Na, NH3, CH3CH2OH
B) LiAlH4
C) NaBH4, CH3CH2OH
D) Zn(Hg), conc. HCl
E) LiAlH[OC(CH3)3]3

34. Which of the following carbonyl compounds may be made from 1,3-dithiane?

1) methyl vinyl ketone

2) 2-pentanone
3) 3,3-dimethyl-2-butanone
4) 2-phenylethanal
A) 1 & 4
B) 2 only
C) 2 & 3
D) 2 & 4

CHAPTER 20

The combination of a carbonyl group and a hydroxyl group on the same carbon atom is called a
_______________ group

A) carbamate
B) carbonate
C) urethane
D) carboxyl
E) carboxylate

2. The common name for pentanedioic acid is:

A) pimelic acid
B) oxalic acid
C) glutaric acid
D) succinct acid
E) adipic acid
3.

What is the common name for the following compound?

A)y-hydroxyvaleric acid
B) y-hydroxypentanoic acid
C) y-hydroxy-y-methylbutyric acid
D) s-hydroxyvaleric acid

4. Carboxylic acid boil at considerably higher temperatures than do alcohols, ketones, or

aldehydes of similar molecular weights. This is because they:

A) have a greater oxygen content

B) are more acidic
C) form stable hydrogen-bonded dimers
D) are hydrophobic
E) none of the above

5. Why are the OH groups of carboxylic acids more acidic than alcohols?

A) resonance stabilization of the carboxylate ion

B) inductive electron donating by the carbonyl oxygen
C) reduced hydrogen bonding capacity
D) because they have lower pKa values
E) none of the above-carboxylic acids are not more acidic than alcohols
6. LOWEST TO HIGHEST

A) 4<3<2<1<5
B) 4<1<3<2<5
C) 5<2<3<1<4
D) 4<1<2<5<3
E) 1<2<4<3<5

7. Which of the following is the strongest acid?

A) chloroacetic acid
B) dichloroacetic acid
C) trichloroacetic acid
D) acetic acid

8. The strongest dichlorobutanoic acid is:

A)2,2-dichlorobutanoic acid
B) 2,3-dichlorobutanoic acid
C) 3,3-dichlorobutanoic acid
D) 3,4-dichlorobutanoic acid
E) 4,4-dichlorobutanoic acid

9. Which of the following compounds is the strongest acid?

A) p-nitrobenzoic acid
B) p-bromobenzoic acid
C) m-methylbenzoic acid
D) m-methoxybenzoic acid
E) water

10. Which of the following statements is true?

A) 100:1
B) 2:1 above
C) 2:1 below
D) 10:1 below
E) equal

11.

Which of the following sequences ranks the structures below in order of increasing acidity?

A) 1<2<3
B) 2<3<1
C) 3<1<2
D) 2<1<3

12. At pH 4.5, which of the following acids would be most dissociated?

A) p-nitrobenzoic acid (3.41)
B) acetic acid (ethanoic acid) ( 4.74)
C) hexanoic acid (4.88)
D)octanoic acid (4.89)
E) water

13. An unknown compound is insoluble in water but dissolves in sodium bicarbonate with a
release of carbon dioxide bubbles. The compound is almost certainly:
A) a carboxylic acid
B) an amine
C) an aldehyde
D) an alkyl chloride
E) an alcohol
14. An ether solution of PhCO2H (A), PhNH2 (B) and PhCH3 (C) is extracted with aqueous
NaOH. The ether layer will contain what compound(s) after extraction? B+C

15. After completing the synthesis of 3-methylpentanoic acid, which of the following treatments
will neutralize the mineral acids and facilitate the distribution of the organic acid from the
organic layer to the aqueous extraction layer?

Extraction with NaHCO3

16. In the propionate ion,

A) both the CO bond lengths are the same.
B) the CO double bond is shorter
C) the CO bond is longer
D) one O atom bears a -1 charge
E) the C atom bears a -1 charge

17. Where would one expect to find the 1H NMR signal for the carboxyl groups hydrogen in
propanoic acid?
A) 4.1-5.6 ppm
B) 10-13 ppm
C) 6.1-7.8 ppm
D) 6.1-7.8 ppm
E) 9.5-10 ppm

18. Which of the following statements is true?

150-180 ppm

19. In the mass spectrum of pentatonic acid, the base peak occurs at m/z _____.
A) 102
B) 101
C) 85
D) 73
E) 60

20. Carboxylic acids can be made from grignards by treating the grignard reagents with :
A) carbon monoxide
B) esters
C) aldehydes
D) diborane
E) carbon dioxide

21. An acid which could not be prepared by the run of an organic halide with cyanide ion
followed by acid hydrolysis of the nitrile is:
A) propanoic acid
B) phenyl acetic acid
C) acetic acid
D) (CH3)3CCO2H
E) CH3(CH2)14CO2H

22. An acid which could not be prepared from an organic halide by carboxylation of the
Grignard reagent is:
A) benzoic acid
B) 2,2-dimethylpropanoic acid
C) propanoic acid
D) 4-oxocyclohexanecarboxylic acid
E) 2-methylbutanoic acid

23. What compound is produced when cyclohexene is tx with concentrated KMnO4?

A) Hexanoic acid
B) adipic acid
C) cyclohexanecarboxylic acid
D) benzoic acid
E) succinic acid

24. What compound is produced when (CH3)2CHCH2Br is subjected to the following sequence
of steps? 1. Mg, Et2O 2. CO2
A) 2-methylpropanoic acid
B) 3-methylpropanoic acid
C) 2-methylbutanoic acid
D) 3-methylbutanoic acid
E) 2-methylhexanoic acid

25. Which sequence of steps below describes the best synthesis of 5-oxohexanoic acid starting
with 1-methylcyclopentan-1-ol?
A) 1. conc KMnO4 2. dry gaseous HBr 3. mg/ether 4. CO2
B) 1. H2SO4 and heat 2. Conc. KMnO4
C) 1. conc KMnO4 2. CH3MgBr/ether 3. H3O+
D) 1. H2SO4 and heat 2. O3 3. (CH3)2S 4. PCC

26. Which of the following conditions will drive the eq of Fischer esterification towards ester
formation?
A) addition of water
B) removal of water as it is formed
C) addition of an inorganic acid as a catalyst
D) addition of alcohol
E) both B and D

27. The methyl ester of a carboxylic acid can be synthesized directly using ______.
A) SOCl2
B) PCl5
C) C2O2Cl2
D) CH2N2
E) CH3NH2

28. Which of the following reactions involves the formation of a methyl ester form a carboxylic
acid?
A) cope elimination
B) hell-volhard-zelinsky reaction
C) reaction with CH2N2
D) hunsdiecker reaction
E) hydroboration with diborane

29. The first mechanistic step in the direct reaction of an amine with a carboxylic acid to produce
an amide is:
A) an acid-base reaction
B) nucleophilic attack on the carbonyl carbon
C) loss of H2O
D) loss of CO2
E) loss of N2

30. LiAl(OC(CH3)3]3H will reduce an acid chloride to an:

A) alcohol
B) alkane
C) acid
D) aldehyde
E) acetal

31.

A) NaBH4
B) LiAlH4
C) BH3-THF
D) Lial[(OC(CH3)3]H
E) none of the above

32.

A) 1. NaBH3-THF 2. H3O+
B) 1. Mg/ether 2. dry CO2 3. H3O+
C) 1. LiAlH4-THF 2. H3O+
D) 1. Hot KMnO4 2. H3O+
E) too long

33. Lithium aluminum hydride (LiAlH4) reduces carboxylic acids to primary alcohols via what
intermediate?
A) a ketone
B) a methyl ester
C) an aldehyde
D) a secondary alcohol
E) an acid chloride

34. Mark all the sequences of reactions that convert a carboxylic acid to an aldehyde. More than
one answer is possible.
A) 1) CH2N2 2) DIBAL 3) H3O+
B) 1) NaBH4 2) H3O+ 3) PCC
C) 1) SOCL2 2) LiAl(Ot-Bu)3H
D) 1) LiAlH4 2) Ag (NH3)2OH

35. The conversion of butanoic acid to 2-pentanone is best accomplished with:

A) 1. Thionyl chloride 2. methylmagnesium bromide
B) methyllithium
C) 1.methanol, sulfuric acid 2. methyl lithium
D 1. thionyl chloride; 2. methanol
E) 1. sulfuric acid; 2. methanol

36. What alkyllithium would react with acetic acid to form 2-butanone?
A) methyllithium
B) vinyllithium
C) ethyllithium
D) propyllithium
E)phenyllithium

37. Esters and amides are most easily made by nucleophilic acyl substitution on:
A) alcohols
B) acid anhydrides
C) carboxylates
D) carboxylic acids
E) acid chlorides

38. Acid chlorides can be prepared from carboxylic acids by treatment with ____.
A) (COCl)2
B) SOCl2
C) KCl
D) both A and B
E) both B and C

39. Which of the following reagents can be used to convert a carboxylic acid directly into its
corresponding acid chloride derivative?
A) (COCl)2
B) HCl
C) CH3Cl
D) NAOCl
E) CH3COCl

ANSWER KEY (CHAPTER 18)

1. B) C, sp2; O, sp2; HCO, ~120°

2. C) an electrophile and a Lewis acid
3. B) shorter and stronger.
4. D) 3-methoxybutanal
5. A) 2-oxocyclohex-3-ene carbaldehyde
6. E) n-butane < diethyl ether < 2-butanone < 1-butanol
7. A) acetone
8. B) has a lower frequency than in a nonconjugated system.
9. C) paraformaldehyde
10. E) PCC
 11. B) Hg2+, H2SO4, H2O
12. E) none of the above
13. B) a ketone
14. C) an aldehyde
15. E) none of the above
16. B) a ketone
17. A) hydrogenation of an acid chloride using Pd/BaSO4/S as a poisoned catalyst
18. D) 1. PCC
2. (CH3)2CHLi/ diethyl ether
3. dilute H3O+
4. Na2Cr2O7/H2SO4 and heat
19. E) all of the above
20. E) 2-methylcyclohexanone < cyclohexanone < CH3CHO < H2CO
21. B) 2 < 3 < 1
22. CH3COCH2CH3 < CH3CH2CHO < H2CO < Cl3CCHO
23. A) 2 < 3 < 1
24. E) carbanion bound to a positively charged heteroatom
25. A) an imine
26. A) imine
27. A) acetal
28. A) H3O⊕

29. A)
30. B) They are more favorable on entropy grounds
31. A) 1. HO-(CH2)2-OH /trace H3O+
2. DMSO (COCl2)/Et3N, CH2Cl2
3. MgBr-(CH2)2-CH3/diethyl ether
4. work-up with H3O+
32. E) a hydrazine
33. D) Zn(Hg), conc. HCl
34. D) 2 & 4

ANSWER KEY (CHAPTER 20)

1. D) carboxyl
2. C) glutaric acid
3. A)y-hydroxyvaleric acid
4. C) form stable hydrogen-bonded dimers
5. A) resonance stabilization of the carboxylate ion
6. B) 4<1<3<2<5
7. C) trichloroacetic acid
8. A) 2,2-dichlorobutanoic acid
9. A) p-nitrobenzoic acid
10. A) 100:1
11. D) 2<1<3
12. A) p-nitrobenzoic acid (pKa=3.41)
13. A) a carboxylic acid
14. C) B+C --------------------------------
15. C) extraction with aq NaHCO3
16. A) Both the CO bonds are the same length
17. B) 10-13 ppm
18. 150-180 ppm
19. E) 60
20. E) carbon dioxide
21. D) (CH3)3CCO2H
22. D) 4-oxocyclohexanecarboxylic acid
23. B) adipic acid
24. D) 3-methylbutanoic acid
25. B) 1. H2SO4
2. Concentrated KMnO4
26. E) both B and D
27. D) CH2N2
28. C) Hunsdiecker reaction
29. A) an acid-base rxn
30. D) aldehyde
31. C) BH3-THF
32. C) 1. LiAlH4-THF 2. H3O+
33. C) an aldehyde
34. A and C
35. B) methyllithium
36. C) ethyllithium
37. E) acid chlorides
38. D) both A and B
39. A) (COCl)2