Ochem Flashcards


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1

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

D) carboxyl

2

The common name for pentanedioic acid is:

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

C) glutaric acid

3
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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

A)y-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

C) form stable hydrogen-bonded dimers

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

A) resonance stabilization of the carboxylate ion

6
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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

B) 4<1<3<2<5

7

Which of the following is the strongest acid?

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

C) trichloroacetic 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

A) 2,2-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

A) p-nitrobenzoic acid

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

A) 100:1

11
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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

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

A) p-nitrobenzoic acid (pKa=3.41)

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

A) a carboxylic acid

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?

C) 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?

C) extraction with aq 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

A) Both the CO bonds are the same length

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

B) 10-13 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

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

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

D) (CH3)3CCO2H

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

D) 4-oxocyclohexanecarboxylic 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

B) adipic 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

D) 3-methylbutanoic 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

B) 1. H2SO4
2. Concentrated KMnO4

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

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

D) CH2N2

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

C) Hunsdiecker reaction

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

A) an acid-base rxn

30

LiAl(OC(CH3)3]3H will reduce an acid chloride to an:
A) alcohol
B) alkane
C) acid
D) aldehyde
E) acetal

D) aldehyde

31
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A) NaBH4
B) LiAlH4
C) BH3-THF
D) Lial[(OC(CH3)3]H
E) none of the above

C) BH3-THF

32
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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

C) 1. LiAlH4-THF 2. H3O+

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

C) an aldehyde

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

A and C

35

The conversion of butanoic acid to 2-pentanone is best accomplished with:
A) 1. Thionyl chloride 2. methylmagnesium bromide
B) bethyllithium
C) 1.methanol, sulfuric acid 2. methyl lithium
D 1. thionyl chloride; 2. methanol
E) 1. sulfuric acid; 2. methanol

B) methyllithium

36

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

C) ethyllithium

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

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

D) both A and B

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

A) (COCl)2