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1 |  |  What is the name of the following compound?
 (11.0K) |
|  | A) | ethylmethylisopropylamine |
|  | B) | ethylpropylsec-butylamine |
|  | C) | ethylmethylpropylamine |
|  | D) | sec-butylethylpropylamin |
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2 |  |  What is the name of the following compound?
 (13.0K) |
|  | A) | dimethylbenzylamine |
|  | B) | N,N-dimethyltoluene |
|  | C) | N,N-dimethylaniline |
|  | D) | dimethylphenolamine |
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3 |  |  What is the name of the following compound?
 (13.0K) |
|  | A) | lithium diisopropylamine |
|  | B) | lithium diisopropylamide |
|  | C) | lithium diisopropylammonium |
|  | D) | diisopropylamine anion |
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4 |  |  Which of the following amines is pyridine? |
|  | A) |  (11.0K) |
|  | B) |  (10.0K) |
|  | C) |  (10.0K) |
|  | D) |  (11.0K) |
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5 |  |  Which of the following amines is a tertiary amine? |
|  | A) |  (13.0K) |
|  | B) |  (13.0K) |
|  | C) |  (12.0K) |
|  | D) |  (13.0K) |
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6 |  |  Which of the following aniline derivatives is the strongest base? |
|  | A) |  (14.0K) |
|  | B) |  (14.0K) |
|  | C) |  (14.0K) |
|  | D) |  (14.0K) |
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7 |  |  Which of the following compounds is most basic? |
|  | A) | cyclohexylamine |
|  | B) | aniline |
|  | C) | p-methoxyaniline |
|  | D) | p-nitroaniline |
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8 |  |  Supply the correct words to complete this sentence:
Electron-withdrawing groups such as nitro _________ the basicity of anilines, especially when substituted _______________. |
|  | A) | increase ; ortho or para |
|  | B) | increase ; meta |
|  | C) | decrease ; ortho or para |
|  | D) | decrease ; meta |
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9 |  |  Which of the following compounds is the strongest acid? |
|  | A) |  (12.0K) |
|  | B) |  (13.0K) |
|  | C) |  (12.0K) |
|  | D) |  (13.0K) |
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10 |  |  Which of the following compounds has the most basic nitrogen?
 (21.0K) |
|  | A) | a |
|  | B) | b |
|  | C) | c |
|  | D) | d |
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11 |  |  Which of the following alkyl halides is not a reasonable substrate for the Gabriel synthesis?
 (18.0K) |
|  | A) |  (10.0K) |
|  | B) |  (13.0K) |
|  | C) |  (10.0K) |
|  | D) |  (12.0K) |
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12 |  |  Predict the product of the following reaction.
Ph–CH2–CN + LiAlH4, Et2O → |
|  | A) | Ph–CH2–CH2–NH2 |
|  | B) | N,N-dimethylaniline |
|  | C) | benzyl ethyl ether |
|  | D) | Ph–CH2–NH2 |
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13 |  |  Predict the product of the following reaction.
Cyclohexanone + Et2NH + NaBH3CN, MeOH → |
|  | A) | N,N-diethylaniline |
|  | B) | N,N-diethylcyclohexylamine |
|  | C) | 3-cyanocyclohexanone |
|  | D) | Et2N–CN |
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14 |  |  What is the sequence of reagents that will accomplish the synthesis of the following aromatic amine from benzene?
 (13.0K) |
|  | A) | CH3Cl, AlCl3; HNO3, H2SO4; H2 |
|  | B) | CH3Cl, AlCl3; HNO3, H2SO4; Fe, HCl; NaOH |
|  | C) | HNO3, H2SO4; Fe, HCl; NaOH; CH3Cl, AlCl3 |
|  | D) | HNO3, H2SO4; CH3Cl, AlCl3; Fe, HCl; NaOH |
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15 |  |  Predict the product of the following reaction.
Et2NH + NaNO2/HCl → |
|  | A) | Et3NH + + Et3N–N=O |
|  | B) | Et2N–N=O |
|  | C) | Et–N2+ |
|  | D) | Et–N=N–OH |
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16 |  |  Predict the product of the following reaction.
Et3N + NaNO2/HCl → |
|  | A) | Et3NH+ + Et3N–N=O |
|  | B) | Et2N–N=O |
|  | C) | Et–N2+ |
|  | D) | Et–N=N–OH |
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17 |  |  Which will be the major product of the following reaction?
 (14.0K)
 (20.0K) |
|  | A) | a |
|  | B) | b |
|  | C) | c |
|  | D) | d |
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18 |  |  What is the product of the following synthesis?
 (21.0K) |
|  | A) |  (15.0K) |
|  | B) |  (14.0K) |
|  | C) |  (14.0K) |
|  | D) |  (13.0K) |
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19 |  |  What is the product of the following synthesis?
 (19.0K) |
|  | A) |  (14.0K) |
|  | B) |  (13.0K) |
|  | C) |  (15.0K) |
|  | D) |  (15.0K) |
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20 |  |  How would you accomplish the following synthesis?
 (14.0K) |
|  | A) | 1. 1 eq. Br2, FeBr3
2. HNO3, H2SO4
3. H2, catalyst
4. HONO, ice bath
5. KI |
|  | B) | 1. Br2, FeBr3
2. HNO2, H2SO4
3. Zn Hg, HCl
4. HONO, room temperature
5. CuI |
|  | C) | 1. HNO3, H2SO4
2. 1 eq. Br2, FeBr3
3. Zn, HCl
4. HONO, ice bath
5. I2 |
|  | D) | 1. HNO2, H2SO4
2. Fe, HCl
3. NaOH
4. HONO, ice bath
5. HI
6. Br2 |
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21 |  |  How would you accomplish the following synthesis?
 (16.0K) |
|  | A) | 1. HNO3, H2SO4
2. NaOH
3. HONO, ice bath
4. Cu2O, H2O
5. NaH
6. MeBr
7. H2, catalyst |
|  | B) | 1. HNO2, H2SO4
2. Fe, HCl
3. NaOH
4. HONO, ice bath
5. Cu2O, H2O
6. MeONa, MeBr |
|  | C) | 1. Sn, HCl
2. HNO2, H2SO4
3. HONO, ice bath
4. Cu2O, H2O
5. MeONa
6. MeBr |
|  | D) | 1. HONO, ice bath
2. Cu2O, H2O
3. NaH
4. MeBr
5. HNO3, H2SO4
6. H2, catalyst
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22 |  |  Predict the product of the following reaction.
Benzenediazonium chloride + CuCN → |
|  | A) | Ph2CuCl |
|  | B) | Ph–CN |
|  | C) | Ph2CuLi |
|  | D) | Ph–N=N–CN |
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23 |  |  Predict the product of the following reaction. p-Nitroaniline + 1) NaNO2, H2SO4 2) KI → |
|  | A) | p-diiodobenzene |
|  | B) | p-dinitrobenzene |
|  | C) | 2,4-dinitroaniline |
|  | D) | p-iodonitrobenzene |
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24 |  |  Predict the product of the following reaction.
2,4-Dibromobenzenediazonium chloride + H3PO2 → |
|  | A) | m-dibromobenzene |
|  | B) | m-bromochlorobenzene |
|  | C) | m-dichlorobenzene |
|  | D) | p-Br–Ph–N=N–Ph |
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25 |  |  Predict the product of the following reaction.
Nitrobenzene + 1) HNO3, H2SO4 2) Fe/HCl 3) NaNO2, HCl 4) Cu2O, CuCl2 |
|  | A) | m-dichlorobenzene |
|  | B) | hydroquinone |
|  | C) | resorcinol |
|  | D) | catechol |
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26 |  |  Which reaction sequence will carry out the following tranformation?
 (16.0K) |
|  | A) | 1) Me2NC6H4NH2 + H2SO4 + NaNO2 2) Add product of 1 to a |
|  | B) | 1) a + H2SO4 + NaNO2 2) Me2NC6H4NH2 |
|  | C) | 1) a + LiAlH4 (excess) 2) H2O, neutralize 3) H2SO4 + NaNO2 4) Me2NC6H4NH2 |
|  | D) | Me2NC6H4N2 , heat |
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27 |  |  What is the minimum structure necessary for the antibiotic activity of a sulfa drug? |
|  | A) |  (12.0K) |
|  | B) |  (13.0K) |
|  | C) |  (12.0K) |
|  | D) |  (14.0K) |
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