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Which would be the product of the following reaction sequence? Which would be the product of the following reaction sequence?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

F) A) and E)
G) A) and B)

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Which reagent(s) would you use to synthesize 2- and 4-bromo-1-cyclopentylbenzene from cyclopentylbenzene?


A) N-Bromosuccinimide (NBS) ,CCl4,light
B) PBr3
C) Br2,FeBr3
D) CH3CH2Br,AlBr3
E) HBr,ROOR

F) B) and C)
G) All of the above

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Which is the best sequence of reactions for the following transformation? Which is the best sequence of reactions for the following transformation?   A)  i) SOCl<sub>2</sub>;ii) C<sub>6</sub>H<sub>6</sub>,AlCl<sub>3</sub>;iii) Zn(Hg) ,HCl;iv) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> B)  i) SOCl<sub>2</sub>;ii) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub>;iii) C<sub>6</sub>H<sub>6</sub>,AlCl<sub>3</sub>;iv) H<sub>2</sub>,Ni C)  i) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub>;ii) SOCl<sub>2</sub>;iii) C<sub>6</sub>H<sub>6</sub>,AlCl<sub>3</sub>;iv) Zn(Hg) ,HCl D)  i) PBr<sub>3</sub>;ii) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub>;iii) C<sub>6</sub>H<sub>6</sub>,AlCl<sub>3</sub>;iv) NaBH<sub>4</sub>,H<sub>2</sub>O E)  Two of these syntheses are satisfactory.


A) i) SOCl2;ii) C6H6,AlCl3;iii) Zn(Hg) ,HCl;iv) HNO3,H2SO4
B) i) SOCl2;ii) HNO3,H2SO4;iii) C6H6,AlCl3;iv) H2,Ni
C) i) HNO3,H2SO4;ii) SOCl2;iii) C6H6,AlCl3;iv) Zn(Hg) ,HCl
D) i) PBr3;ii) HNO3,H2SO4;iii) C6H6,AlCl3;iv) NaBH4,H2O
E) Two of these syntheses are satisfactory.

F) A) and B)
G) C) and D)

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Propose a reasonable synthesis of the following compound from benzene. Propose a reasonable synthesis of the following compound from benzene.

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The major product(s) ,A,of the following reaction, The major product(s) ,A,of the following reaction,   would be: A)  I B)  II C)  A mixture of I and II D)  III E)  IV would be:


A) I
B) II
C) A mixture of I and II
D) III
E) IV

F) A) and D)
G) A) and C)

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Which reagent(s) would you use to carry out the following transformation? isopropylbenzene -- \rightarrow 2- and 4-chloro-1-isopropylbenzene


A) Cl2,light,and heat
B) Cl2,FeCl3
C) SOCl2
D) C2H5Cl,AlCl3
E) HCl,peroxides

F) B) and C)
G) A) and D)

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Which of the following compounds would you expect to be most reactive toward ring nitration?


A) Benzene
B) Toluene
C) m-Xylene
D) o-Xylene
E) Benzoic acid

F) B) and D)
G) B) and C)

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The major product(s) of the following reaction, The major product(s) of the following reaction,   would be: A)  I B)  II C)  III D)  IV E)  V would be:


A) I
B) II
C) III
D) IV
E) V

F) C) and D)
G) A) and B)

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Which of the following compounds would be most reactive to ring bromination? Which of the following compounds would be most reactive to ring bromination?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

F) A) and B)
G) All of the above

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Which reagent would you use to carry out the following transformation? tert-butylbenzene -- \rightarrow P-tert-butylbenzenesulfonic acid + O-tert-butylbenzenesulfonic acid


A) HNO3/H2SO4
B) tert-C4H9Cl/AlCl3
C) H2SO3/peroxides
D) SO3/H2SO4
E) SO2/H2SO3

F) A) and E)
G) D) and E)

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Which is the best sequence of reactions for the following transformation? Which is the best sequence of reactions for the following transformation?   A)  i) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub>;ii) CH<sub>3</sub>MgBr,Et<sub>2</sub>O;iii) H<sub>3</sub>O<sup>+</sup>,heat B)  i) CH<sub>3</sub>MgBr,Et<sub>2</sub>O;ii) H<sub>3</sub>O<sup>+</sup>,heat;iii) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub> C)  i) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub>;ii) NaBH<sub>4</sub>,H<sub>2</sub>O;iii) H<sub>3</sub>O<sup>+</sup>,heat D)  i) HNO<sub>3</sub>,H<sub>2</sub>SO<sub>4</sub>;ii) LiAlH<sub>4</sub>,H<sub>2</sub>O;iii) H<sub>3</sub>O<sup>+</sup>,heat E)  None of these syntheses is satisfactory.


A) i) HNO3,H2SO4;ii) CH3MgBr,Et2O;iii) H3O+,heat
B) i) CH3MgBr,Et2O;ii) H3O+,heat;iii) HNO3,H2SO4
C) i) HNO3,H2SO4;ii) NaBH4,H2O;iii) H3O+,heat
D) i) HNO3,H2SO4;ii) LiAlH4,H2O;iii) H3O+,heat
E) None of these syntheses is satisfactory.

F) None of the above
G) D) and E)

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What would be the major product of the following reaction? What would be the major product of the following reaction?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

F) A) and D)
G) B) and E)

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The major product(s) ,D,of the following reaction The major product(s) ,D,of the following reaction   would be: A)  I B)  II C)  III D)  IV E)  Equal amounts of I and II would be:


A) I
B) II
C) III
D) IV
E) Equal amounts of I and II

F) B) and E)
G) None of the above

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What would you expect to be the major product(s) obtained from the mononitration of m-dichlorobenzene? What would you expect to be the major product(s) obtained from the mononitration of m-dichlorobenzene?   A)  I B)  II C)  III D)  Equal amounts of I and II E)  Equal amounts of I,II and III


A) I
B) II
C) III
D) Equal amounts of I and II
E) Equal amounts of I,II and III

F) B) and E)
G) C) and D)

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The major product(s) of the following reaction, The major product(s) of the following reaction,   A)  I B)  II C)  A mixture of I and II D)  III E)  IV


A) I
B) II
C) A mixture of I and II
D) III
E) IV

F) C) and D)
G) A) and C)

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Which of the following carbocations would be most stable?


A)
Which of the following carbocations would be most stable? A)    B)    C)    D)    E)
B)
Which of the following carbocations would be most stable? A)    B)    C)    D)    E)
C)
Which of the following carbocations would be most stable? A)    B)    C)    D)    E)
D)
Which of the following carbocations would be most stable? A)    B)    C)    D)    E)
E)
Which of the following carbocations would be most stable? A)    B)    C)    D)    E)

F) B) and E)
G) A) and C)

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Which alkyl halide would be most reactive in an SN2 reaction?


A) C6H5CH2CH2CH2Br
B)
Which alkyl halide would be most reactive in an S<sub>N</sub>2 reaction? A)  C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br B)    C)    D)    E)
C)
Which alkyl halide would be most reactive in an S<sub>N</sub>2 reaction? A)  C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br B)    C)    D)    E)
D)
Which alkyl halide would be most reactive in an S<sub>N</sub>2 reaction? A)  C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br B)    C)    D)    E)
E)
Which alkyl halide would be most reactive in an S<sub>N</sub>2 reaction? A)  C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br B)    C)    D)    E)

F) C) and E)
G) A) and C)

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Which would be a good synthesis of m-nitrobenzoic acid?


A)
Which would be a good synthesis of m-nitrobenzoic acid? A)    B)    C)    D)  More than one of the above E)  None of the above
B)
Which would be a good synthesis of m-nitrobenzoic acid? A)    B)    C)    D)  More than one of the above E)  None of the above
C)
Which would be a good synthesis of m-nitrobenzoic acid? A)    B)    C)    D)  More than one of the above E)  None of the above
D) More than one of the above
E) None of the above

F) A) and C)
G) A) and B)

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What would you expect to be the major product obtained from the following reaction? What would you expect to be the major product obtained from the following reaction?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

F) A) and B)
G) A) and D)

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Substituent groups affect both _____________ and _______________ in electrophilic aromatic substitution reactions.

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reactivity...

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