Final 020

Made by: Rahaf Turab

& Lara Fryjat
 Final 020
Q1: What is the number of configurational stereoisomers is
possible for each of the following molecules:

a. I has 2 stereoisomers; II has 0

b. I has 4 stereoisomers; II has 0
c. I has 2 stereoisomers; II has 2
d. I has 3 stereoisomers; II has 4
e. I has 4 stereoisomers; II has 2

Answer:b

Q2: Which carbonyl compound reacts fastest with nucieophiles?

a. 2,2-dimethylbutanal
b. Cyclopentanone
c. 2,4,6-trimethylbenzaldehyde
d. Acetone
e. 2,2-dichloropropanal
Answer:e
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Q3: what is the major product of the following reaction?

a. A
b. B
c. C
d. D
e. E

Answer: e

Q4: what is the correct name of the following molecule?

a. (2R,3R)-2-bromo-3-chlorobutane
b. (2S,3R)-2-bromo-3-chlorobutane
c. (2S,3S)-2-bromo-3-chlorobutane
d. racemic-2-bromo-3-chlorobutane
e. (2R,3S)-2-bromo-3-chlorobutane

Answer:e

Q5: what major product(s) will be found from this reaction?

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a. I
b. II and IV
c. III
d. II
e. IV
Answer:d

Q6:

a. 6-methyl-4-heptanonoic acid
b. 6-methyl-4-oxoheptanoic acid
c. 6-methyl-1-hydroxy-1,4-heptandione
d. 5-isopropyl-4-oxopentanoic acid
e. 5-methyl-3-oxohexanoic acid

Answer:b
Q7: what is the relationship between the following pair of
molecules?

a. Identical
b. Constitutional isomers
c. Conformers
d. Enantiomers
e. Cis-trans isomers Answer:c
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Q8: In the reaction below, the product is?

a. III and IV
b. III only
c. IV only
d. I and V
e. II only
f. I only

Answer:d
Q9: which reaction sequence converts benzene into m-chloroiodobenzene?

a. 1) Cl2/FeCl3, 2) HCL, then KI

b. 1) KI/Cu2I3(0º C), 2) Cl2/FeCl3
c. 1) Cl2/FeCl3, 2) HNO3/H2SO4, 3) SnCl2/HCL, 4) NaNO2/H+(0º
C), then KI
d. 1) Cl2/FeBr3, 2) SnCl2/HCL, 3)HNO3/H2SO4, 4)
NaNO2/HBr/Cu2Br2(0º C)
e. 1) HNO3/H2SO4, 2) Cl2/FeCl3, 3)SnCl2/HCL, 4) NaNO2/H+(0º
C), then KI
Answer:e
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Q10: The alcohol which reacts fastest with Lucas’s reagent
(HCl/ZnCl2) is:

a. Isobutyl alcohol
b. Isopropyl alcohol
c. 1-butnol
d. 2-methyl-2-butanol
e. Sec-butyl alcohol

Answer:d

Q11: Which of the following compounds is never chiral?

a. 1-bromo-2-chlorobutane
b. 1,2-dichlorobutane
c. 1,4-dibromobutane
d. 1,3-dibromobutane
e. 2,3-dibromobutane

Answer:c

Q12: Which is the electrophilic reagent generated in this reaction?

a. V
b. I
c. II
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d. IV
e. III
Answer:d

Q13: In the structure below which carbon atom (A, B, D, R, X,

and Z) is the most electronegative

a. D
b. Z
c. X
d. B
e. R
f. A
Answer:f

Q14: What is the major product of the following reaction?

a. III
b. II
c. I
d. IV
e. V Answer:a
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Q15: Which structure is a correct resonance structure of this molecule?

a. II only
b. I only
c. IV only
d. I and III
e. III only

Answer:a

Q16: Starting with p-bromonitrobenzene what sequence of reactions

will produce nitrobenzene?
a. 1. H2O, 2.Mg/ether
b. 1. Br2/AlBr3, 2.Mg/ether, 3.D2O
c. 1. Mg/ether, 2.H2O
d. 1. H2O, 2.Br2/AlBr3
e. 1. H2SO4, 2.Mg/ether, 3. D2O

Answer:c
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Q17: What is the relationship between the following pair?

a. Enantiomers
b. Conformers
c. Diastereomers
d. Identical
e. Constitutional isomers

Answer:e

Q18: What is the major product of the following reaction?

a. A
b. B
c. C
d. D
e. E

A
A
Answer:a
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Q19: The product (X) is:

a. A
b. B
c. C
d. D
e. E

Answer:d

Q20: What starting material would give this

compound as major product?

a. Butanone + NH3/H2O
b. Ethyl methy ketone + hydrazine + H2O
c. 1-butene + HBr, then NH3/H2O
d. 2-butene + NH2OH
e. Butanone + hydroxylamine

Answer:e

Q21: What products will be formed when 2-butene is treated with

m-choloperbenzoic acid (peroxyacid) followed by methanol/H+?

a. 3-chlorobutan-2-ol
b. 2,3-butanediol
c. 2-butene oxide
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d. Butyl methyl ketone
e. 3-methoxybutan-2-ol

Answer:e
Q22: Which carbonyl compound reacts fastest with nucleophiles:

a. 2,2-dichloropropanal
b. Cyclopentanone
c. 2,4,6-trimethylbenzaldehyde
d. 2,2-dimethylbutanal
e. Acetone
Answer:a

Q23: Which is the electrophilic reagent generated in this reaction?

a. III
b. IV
c. V
d. II
e. I
Answer:a
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Q24: Which molecular formula corresponds to a cycloalkene?

a. C11H16
b. C9H12
c. C10H18
d. C8H18
e. C7H14

Answer:c

Q25: The product(s) in the following reaction is(are):

a. II only
b. I and IV
c. V only
d. IV only
e. III and V

Answer:d
Q26: Starting with p-bromotoluene what sequence of reactions will
produce p-deuteriotoluene?
a. 1. D2O, 2.Mg/ether
b. 1. H2SO4, 2. Mg/ether, 3.D2O
c. 1. Br2/AlBr3, 2.Mg/ether, 3. D2O
d. 1. Mg/ether, 2. D2O
e. 1. D2O, 2.Br2/AlBr3
Answer:d
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Q27: In the following reaction, the product
(X) is:

a. A
b. B
c. C
d. D
e. E

Answer:b

Q28: What is the correct IUPAC name of the following compound:

Cl
a. 3-chloro-2-methyl-1-cyclohexene
b. 1-chloro-2-methylcyclohexene
c. 2-chloro-1-methylcyclohexene
d. 3-chloro-2-methylcyclohexene
e. 6-chloro-1-methylcyclohexene

Answer:e

Q29: In the reaction below, the product is (are):

a. IV and V
b. III and V
c. I only
d. V only
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e. I and II

Answer:b

Q30: The alcohol which reacts slowest with Lucas’s reagents

(HCl/ZnCl2) is:

a. Tert-butyl alcohol
b. 1-pentanol
c. Cyclopentanol
d. Sec-butyl alcohol
e. 2-propanol Answer:b

Q31:Which of the following water-insoluble compounds becomes

soluble upon addition of NaOH?
a. Cycloheptene
b. Acetophenone
c. 2-octanol
d. m-ethylphenol
e. m-bromoaniline

Answer:a
Q32: What starting materials would give this compound as major
product? H2N
N
a. Cyclopentene + NH3/NaOH
b. Cyclopentanone + NH3(excess)
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c. Cyclopentanone + hydroxylamine
d. Cyclopentene + HBr, then NH3/OH-

e. Cyclopentanone + hydrazine

Answer:e

Q33: The product of the following reaction is

a. A
b. B
c. C
d. D
e. E

Answer:d

Q34: Which of the following phenols is the most acidic?

a. 2,4,6-trimethylphenol
b. 2,4-dimethylphenol
c. p-tert-butylphenol
d. 2,4-dichlorophenol
e. 3-chlorophenol

Answer:d
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Q35: Which structure represents a correct resonance structure for
the following molecule:

a. A
b. B
c. C
d. D
e. E

Answer: a

Q36: Which of the following compounds is never chiral?

a. 1-cyclopropyl-2-fluoro-butane
b. 2,3-dicyclopropylbutane
c. Butane-1,2-diol
d. 1,4-diiodobutane
e. 1,3-difluorobutane

Answer:d
Q37: The product(s) in the following reaction is(are):

a. II and III
b. V only
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c. III and IV
d. III only
e. IV only

Answer:b

Q38: The best Williamson synthesis of sec-butyl methyl ether

involves the following reaction:
a. 2-bromobutane + bromomethane in basic media
b. Sodium sec-butoxide + methyl bromide
c. 2-butanol + methanol in acidic media
d. 1-butene + methanol in acidic media
e. 2-bromobutane + sodium methoxide answer:b

Q39: In the structure below which carbon atom (A, B, D, R, X

and Z) is the most electronegative

a. D
b. B
c. Z
d. A
e. R
f. X Answer:f
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Q40: What is the correct IUPAC name of the following F

compound:

a. 1-fluoro-2—methylcyclohexene
b. 6-fluoro-1-methylcyclohexene

Answer:b

Q41: Which carbonyl compound reacts slowest with nucleophiles?

a. Acetaldehyde
b. Cyclohexanone
c. Diethyl ketone
d. Formaldehyde
e. Diisopropyl ketone

Answer:e

Q42: What is the relationship between the following pair?

a. Identical
b. Enantiomers
c. Conformers
d. Not isomers
e. Diastereomers

Answer:d
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Q43: The product of the following reaction is

a. A
b. B

c. C
d. D

Answer:c

Q44: The best Williamson synthesis of isopropyl methyl ether

involves the following reaction:

a. 2-bromopropene + bromomethane in basic media

b. Propene + methanol in acidic media
c. Isopropyl bromide + sodium methoxide
d. Sodium isopropoxide + methyl bromide
e. 2-propanol + methanol in acidic media
Answer:d
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Q45: What is the major product of the following reaction?

a. A
b. B
c. C
d. D

Answer:b

Q46: Which reaction sequence converts benzene into m-

bromochlorobenzene?
a. 1) HBr/Cu2Br2, 2) HCl/Cu2Cl2(0ºC)
b. 1) Br2/FeBr3, 2) HCl/Cu2Cl2(0 ºC)
c. 1) HNO3/H2SO4, 2) Br2/FeBr3, 3) SnCl2/HCl, 4)
NaNO2/HCl/Cu2Cl2(0 ºC)
d. 1)Cl2/FeCl3, 2) SnBr2/HBr, 3) NaNO2/HCl/Cu2Br2(0 ºC)
e. 1) Br2/FeBr3, 2)HNO3/H2SO4, 3)SnCl2/HCl, 4)
NaNO2/HCl/Cu2Cl2(0 ºC)

Answer:c
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Q47: The product(s) in the following reaction is(are)

Answer: I and IV

Q48: What is the major product of the

following reaction?

a. A
b. B
c. C
d. D

Answer:b
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Q49: What is the relationship between the following pair of
molecules?

a. Cis-trans isomers
b. Enantiomers
c. Constitutional isomers
d. Conformers
e. Identical

Answer:c

Q50: Which combination of reactants form a cyanohydrin?

a. Benzaldehyde + HCN/NaOH
b. Benzyl alcohol + HCN/NaOH
c. Bromobenzene + NaCN
d. Phenol + NaCN
e. Benzoic acid + HCN/NaOH

Answer:a

Q51: What starting materials would give this compound as major

product?

a. Benzaldehyde + aniline
b. Acetophenone + aniline
c. Benzaldehyde + phenylhydrazine
d. Benzaldehyde + hydroxylamine
e. Acetophenone + aniline Answer:c
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Q52: Which of the following is least reactive toward nucleophilic
acyl substitution?
a. CH3COCI
b. CH3CO2CH3
c. CH3CONH2
d. C6H5CO2CH3
e. CH3COOCOCH3

Answer:c

Q53: The product(s) in the following reaction is(are)

a. I and II
b. V only
c. III and IV
d. III only
e. IV only

Answer:d

Q54: The electrophilic reagent in the

following reaction is:

a. A
b. B
Answer:a
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Q55: Which of the following is most reactive toward substitution
within KCN?

a. A
b. B
c. C

Answer:b

Q56: What is the major product of the following reaction?

a. A
b. B
c. C
d. D
e. E

Answer:d
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Q57: The product of the following reaction

is:
a. A
b. B
c. C
d. D

Answer:a

Q58: Starting with p-bromonitrobenzene what sequence of

reactions will produce p-deuterionitrobenzene?
a. 1) Mg/ether 2)D2O
b. 1) D2O 2) Mg/ether
c. 1) Br2/AlBr3, 2) Mg/ether, 3) D2O
d. 1) D2O, 2) Br2/AlBr3
e. 1) H2SO4, 2) Mg/ether, 3) D2O

Answer:a
Q59: What products will be formed when cyclopentene is treated
with m-choloperbenzoic acid (peroxyacid) followed by
methanol/H+?

a. Cyclopentanecarboxylic acid
b. 2-methoxycyclopentanol
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c. 2-chlorocyclopentanol
d. 1,2-cyclopentandiol
e. Cyclopentene oxide

Answer:b

Q60: Which of the following is Least reactive toward substitution

with CH3MgBr?

a. A
b. B
c. C

Answer:a

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