Exam
Name___________________________________
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
1) Identify the best product for the reaction.
1)
A)
B)
C)
D)
E)
1
2) Identify the best product for the reaction.
2)
A)
B)
C)
D)
E)
3) Identify the major product for the reaction.
3)
A)
2
B)
C)
D)
E)
4) Identify the major product(s) for the reaction.
4)
A)
3
B)
C)
D)
E)
5) What is the common name for the following compound?
A)
B)
C)
D)
E)
-chlorobutanoic acid
-chlorobutyric acid
3-chlorobutyric acid
-chlorobutanoic acid
-chlorobutyric acid
4
5)
6) What is the IUPAC name for the following compound?
A)
B)
C)
D)
E)
6)
benzyl acetate
phenyl acetate
benzyl methylacetate
methyl benzoate
methyl phenylacetate
7) Which of the following compounds is N,N-dimethylbenzamide?
A) I
B) II
C) III
D) IV
7)
E) V
8) What is the hybridization and geometry of the carbonyl carbon in carboxylic acids and their
derivatives?
A) sp3 , trigonal planar
B) sp, trigonal planar
C) sp2 , trigonal planar
D) sp3 , tetrahedral
E) sp2 , tetrahedral
8)
9) Which of the following compounds has the lowest boiling point?
A) 1-butanol
B) butanamide
C) methyl propanoate
D) butanoic acid
E) butanenitrile
9)
5
10) Piperine, a major component of black pepper, is shown below. To what class of carboxylic
acid derivative does piperine belong?
A)
B)
C)
D)
E)
10)
acyl halide
nitrile
amide
acid anhydride
ester
11) Which reaction coordinate diagram best represents the reaction that occurs when NaNH2
reacts with CH3 COCl to form acetamide?
A)
B)
6
11)
C)
D)
E)
12) In nucleophilic acyl substitution,
A) loss of the leaving group is followed by rearrangement of the carbocation.
B) ester hydrolysis is followed by deprotonation.
C) protonation of the carbonyl is followed immediately by loss of the leaving group.
D) an SN2 reaction occurs.
E) addition to the carbonyl by a nucleophile is followed by loss of the leaving group.
7
12)
13) Which of the following compounds is most reactive toward nucleophilic acyl substitution?
A)
13)
B)
C)
D)
E)
14) Which of the following compounds is the least reactive toward nucleophilic acyl substitution?
A)
B)
C)
D)
E)
8
14)
15) Which of the following is the best method for preparing
15)
A)
B)
C)
D)
E)
16) Esters and amides are most easily made by nucleophilic acyl substitution reactions on:
A) acid anhydrides.
B) alcohols.
C) carboxylates.
D) acid chlorides.
E) carboxylic acids.
16)
17) Which of the following compounds would yield acetic acid when hydrolyzed under heat?
A)
17)
B) CH3 C N
C)
D)
E) all the above
9
18) Which of the following is (are) formed in the reaction between ethyl butanoate and ethyl
amine?
A) N-ethylbutanamide
B) 1-butanol
C) ethanol
D) both A and C
E) both B and C
18)
19) Which of the following is one of the steps in the mechanism of the following reaction?
19)
A)
B)
C)
D)
E)
10
20) Which of the following intermediates is present in the acid-catalyzed hydrolysis of
t -butylacetate but not in the acid-catalyzed hydrolysis of methyl acetate?
A) a protonated carbonyl
B) a carbocation
C) a carboxylate anion
D) 1-propanol
E) a carbanion
20)
21) What is the product obtained from the following reaction?
21)
A) I
B) II
C) III
D) IV
11
E) V
22) What is the major organic product of the following reaction?
A) I
B) II
C) III
22)
D) IV
E) V
23) Which of the following conditions will drive the equilibrium of the 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
23)
24) Which of the following methods can be used to prepare
CH3 C N?
A) CH3 Br + - C N
B) CH3 CH2 C N + Br2
24)
C) CH3 CH2 Br + NH3
D) A and B
E) B and C
12
25) What is the major organic product obtained from the following sequence of reactions?
25)
A)
B)
C)
D)
E)
26) Which of the following reagents is used in the following reaction?
A) Cl2 /P
B) PCl3
C) HCl
D) Cl2 /CCl4
13
26)
E) Cl2 /h
27) What is the major product of the following reaction?
A) I
B) II
C) III
27)
D) IV
14
E) V
28) Give the product of the reaction.
28)
A)
B)
C)
D)
E)
29) What is the IUPAC name for the following compound?
A)
B)
C)
D)
E)
29)
-bromobutyraldehyde
2-bromobutanal
3-bromobutanone
-bromobutanal
3-bromobutanal
30) Which of the following characterizes the reactions of aldehydes and ketones?
A) nucleophilic acyl substitution
B) electrophilic addition
C) nucleophilic addition; free radical addition
D) electrophilic substitution
15
30)
31) Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic
acyl substitution reactions?
A) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde.
B) Once the nucleophile adds to an aldehyde, neither H- nor R- can be eliminated since they
are strongly basic.
C) Once the nucleophile adds to an aldehyde, the tetrahedral intermediate is too sterically
hindered to eliminate one of the attached groups.
D) The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2
hybridized.
E) Aldehydes are more sterically hindered than esters.
31)
32) What is the major product when (CH3 ) 2 CHCH2 CH2 Br is subjected to the following reaction
sequence: 1. Mg, ether 2. CO2 3. H3 O+ ?
32)
33) Which of the following reactions can be used to prepare 3-methyl-3-hexanol,
33)
A) 2-methyl-2-butanol
C) 3-methyl-1-butanol
B) 4-methylpentanoic acid
D) 4-methyl-1-pentanol
A)
B)
C)
D) A and B
E) A, B, and C
16
34) What is/are the major product(s) of the following reaction?
34)
A)
B)
C)
D)
E)
35) Which of the following reactions is the best method for preparing acetaldehyde?
A)
B)
17
35)
C)
D)
E)
36) What is the major product of the following reaction?
A) I
B) II
C) III
36)
D) IV
E) V
37) Diisobutylaluminum hydride (DIBALH) can be used to carry out which of the following
conversions?
A) 2 alcohol to ketone
B) ester to ketone
C) carboxylic acid to ester
D) aldehyde to carboxylic acid
E) ester to aldehyde
18
37)
38) Which of the following is the best method for preparing lactic acid from acetaldehyde?
38)
A) CH3 MgBr; - OH
B) Cl2 ; - OH; CH3 OH
C) KMnO4 ; - OH
D) HC N; H3 O+ /heat
E) Cl2 ; Mg/ether; - OH
39) Which of the sequences works best to accomplish the following conversion?
39)
A) 1. H2 NCH2 MgBr 2. H3 O+
B) 1. NaCN, HCl 2. H2 , Pt
C) 1. NH3 , H+ 2. H2 , Pt
D) 1. H2 NNH2 , H+ 2. H3 O+
E) 1. NaNH2 2. H3 O+
40) What class of organic compounds results when cyclopentanone reacts with ethylamine in the
presence of trace acid?
A) cyanohydrin
B) imine
C) semicarbazone
D) oxime
E) enamine
40)
41) When the carbonyl group of a neutral ketone is protonated,
A) the resulting species becomes more electrophilic.
B) the resulting species has a positive charge.
C) the resulting species is activated toward nucleophilic attack.
D) subsequent nucleophilic attack on the resulting species is said to occur under
acid-catalyzed conditions.
E) all of the above
41)
19
42) What is the major organic product of the following reaction?
42)
A)
B)
C)
D)
E)
43) What is the major organic product of the following reaction?
A) I
B) II
C) III
43)
D) IV
20
E) V
44) The compound:
44)
can form a hemiacetal by reacting with itself in solution. What is the structure of this
hemiacetal?
A) I
B) II
C) III
D) IV
E) V
45) What is the major product of the following reaction?
A) I
B) II
C) III
45)
D) IV
21
E) V
46) What carbonyl compound and what phosphonium ylide are required for the synthesis of the
following alkene?
A) I
B) II
C) III
D) II or III
46)
E) I, II, or III
47) Which of the following synthetic routes works best for preparing 4-octene?
A) CH3 CH2 CH=PPh3 + CH3 CH2 CH2 CH2 CHO
B) CH3 CH2 CH2 CH=PPh3 + CH3 CH2 CH2 CHO
C) 4-bromooctane + KOC(CH3 ) 3
D) CH3 CH2 CH2 CH2 MgBr + CH3 CH2 CH2 CHO
E) 4-bromooctane + NaOCH3
47)
48) What reagent(s) would you use to accomplish the following conversion?
48)
A) CH3 MgBr; H3 O+
B) CH3 Br; H3 O+
C) (CH3 ) 2 CuLi; H3 O+
D) CH3 Br; LiAlH4 ; H3 O+
E) LiAlH4 ; CH3 MgBr; H3 O+
22
49) Which of the following compounds does not have an alpha hydrogen?
A)
B)
C)
D)
E)
49)
I
II
III
IV
all of the above
50) Which of the labeled hydrogen atoms in the following structure is the most acidic?
A) 1
B) 2
C) 3
D) 4
23
E) 5
50)
51) Which of the following underlined alpha hydrogens are the most acidic?
A)
51)
B)
C)
D)
E)
52) Which compound has the lowest pKa?
A) (CH3 CH2 O2 C)2 CH2
52)
B) CH3 CH2 O2 CCH2 CHO
C) CH3 CH2 COCH2 CHO
D) PhCOCH2 COCH3
E) (NC)2 CH2
24
53) When compared to the keto form, the enol form of which of the following compounds is most
stable?
A) I
B) II
C) III
D) IV
54) Which of the following compounds has the most stable enol tautomer?
A)
B)
C)
D)
E)
25
53)
E) V
54)
55) How many Hs in the compound below are replaced by Ds when it is shaken in D2 O
55)
containing trace hydroxide?
A) 1
B) 2
C) 3
D) 6
56) How would you accomplish the following conversion?
E) 7
56)
A) Br2 /H+ , H2 O; NaC N
B) - OH/NaC N
C) H+ /H2 O; HC N
D) LiAlH4 ; HC N; KMnO4
E) HBr; NaC N
57) Which of the following compounds will give a positive iodoform test?
A) benzophenone
B) propanal
C) 2-pentanone
D) 3-pentanone
E) cyclohexanone
57)
58) The Hell-Volhard-Zelinsky reaction involves:
A) the oxidation of aldehydes to acids.
B) the -bromination of ketones.
C) the -bromination of carboxylic acids.
D) the bromination of alcohols.
E) none of the above
58)
26
59) Which is the major organic product from the following reaction?
59)
A)
B)
C)
D)
E)
60) Identify the major organic product of the following sequence.
A)
B)
C)
D)
E)
2-cyclohexenone
3-bromocyclohexanone
3-hydroxycyclohexanone
4-bromocyclohexanone
4-hydroxycyclohexanone
27
60)
61) What is the major organic product of the following reaction?
A) I
B) II
C) III
61)
D) IV
E) V
62) Which of the following methods can be used to prepare the following compound?
A)
B)
C)
D)
E)
I
II
III
II and III
I, II, and III
28
62)
63) In the Michael reaction, addition to the , -unsaturated carbonyl occurs in a:
A) 1,4-fashion.
B) 1,2-fashion.
C) 1,5-fashion.
D) Diels-Alder reaction.
E) 1,3-fashion.
63)
64) What is the major organic product of the following reaction?
64)
A) I
B) II
C) III
D) IV
E) V
65) Which of the following aldehydes does not undergo an aldol addition when mixed with base?
A) I
B) II
C) III
D) IV
29
E) V
65)
66) What is the major organic product of the following aldol addition?
A) I
B) II
C) III
D) IV
66)
E) V
67) What is the major organic product of the following addition?
A) I
B) II
C) III
67)
D) IV
30
E) V
68) What is the major product of the following condensation?
A) I
B) II
C) III
68)
D) IV
E) V
69) What materials are needed to prepare the following product?
A) I
B) II
C) III
D) IV
31
69)
E) V
70) What is the major organic product of the following reaction?
A) I
B) II
C) III
70)
D) IV
E) V
71) What materials would you use to prepare the following compound using a Robinson
Annulation?
A) I
B) II
C) III
D) IV
32
E) V
71)
72) What alkyl bromide should be used in the malonic ester synthesis of the following carboxylic
acid?
A) I
B) II
C) III
D) IV
E) V
73) What alkyl bromide should be used in the acetoacetic ester synthesis of the following methyl
ketone?
A) I
B) II
C) III
D) IV
74) Give the major product for the following reaction.
A)
33
72)
73)
E) V
74)
B)
C)
D)
E)
34
75) Give the major product for the following reaction.
A)
B)
C)
D)
E)
35
75)