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1 | | How many alkenes are formed by E2 elimination of HBr from 2-bromo-2,3-dimethylhexane using a strong base such as sodium methoxide? |
| | A) | 1 |
| | B) | 2 |
| | C) | 3 |
| | D) | 4 |
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2 | | How many alkenes are formed by E2 elimination of HBr from 3-bromo-3,4-dimethylhexane using a strong base such as sodium methoxide? |
| | A) | 2 |
| | B) | 3 |
| | C) | 4 |
| | D) | 5 |
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3 | | How many alkenes are formed by E1 elimination of HCl from 3-chloro-3,4-dimethylheptane in methanol? |
| | A) | 2 |
| | B) | 3 |
| | C) | 4 |
| | D) | 5 |
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4 | | Which of the following is NOT reasonable for an elimination reaction? |
| | A) | (12.0K) |
| | B) | (12.0K) |
| | C) | (13.0K) |
| | D) | (11.0K) |
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5 | | Which is the major product of the following reaction? (14.0K) |
| | A) | (13.0K) |
| | B) | (13.0K) |
| | C) | (11.0K) |
| | D) | (11.0K) |
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6 | | Potassium tert-butoxide is often used to effect dehydrohalogenation. Which of the following statements does NOT describe this compound? |
| | A) | Its molecular weight is greater than ethanol’s. |
| | B) | It is a weak base. |
| | C) | It is sterically hindered. |
| | D) | It is an ionic compound. |
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7 | | “Dehydrohalogenation” describes a reaction in the course of which a halogen is eliminated and a double bond is formed. What else is also eliminated? |
| | A) | water |
| | B) | hydronium ion |
| | C) | hydrogen |
| | D) | another halogen |
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8 | | In dehydrohalogenation, what removes hydrogen from the alkyl halide? |
| | A) | a base |
| | B) | an acid |
| | C) | a leaving group |
| | D) | a double bond |
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9 | | What is the major product of the following reaction? (16.0K) |
| | A) | (12.0K) |
| | B) | (12.0K) |
| | C) | (15.0K) |
| | D) | (15.0K) |
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10 | | Which of the following statements is TRUE for an E1 reaction? |
| | A) | The E1 reaction requires a strong base to take place. |
| | B) | Primary and secondary alkyl halides are a good substrate for the E1 reaction. |
| | C) | The E1 reaction occurs during the solvolysis of tertiary alkyl halides. |
| | D) | The rate of the E1 vs. SN1 reaction increases at lower temperature. |
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11 | | What is the major product of the following reaction? (15.0K) |
| | A) | (12.0K) |
| | B) | (12.0K) |
| | C) | (12.0K) |
| | D) | (15.0K) |
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12 | | Give all of the expected products of the following reaction. (16.0K) (15.0K) |
| | A) | a |
| | B) | a and b |
| | C) | c and d |
| | D) | a and d |
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13 | | Give all of the expected products of the following reaction. (11.0K) (13.0K) |
| | A) | a |
| | B) | a and c |
| | C) | a, b, c, and d |
| | D) | a, c, and d |
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14 | | Why does E2 elimination occur more rapidly in cis-2-chloro-1,1,3-trimethylcyclohexane than in the trans isomer? |
| | A) | The leaving group and alpha hydrogen are both equatorial for the cis case. |
| | B) | The leaving group and alpha hydrogen are both axial for the cis case. |
| | C) | The leaving group is axial and the alpha hydrogen is equatorial for the cis case. |
| | D) | The leaving group is equatorial and the alpha hydrogen is axial for the cis case. |
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15 | | In the E1 reaction, how is the rate affected when the concentration of attacking nucleophile is doubled? |
| | A) | The rate is doubled. |
| | B) | The rate is halved. |
| | C) | The rate quadruples. |
| | D) | The rate is unchanged. |
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16 | | A strong base is needed for |
| | A) | E1 only. |
| | B) | E2 only. |
| | C) | both E1 and E2. |
| | D) | neither E1 nor E2. |
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17 | | Which of the following statements about E2 elimination from an alkyl halide using sodium methoxide as base is FALSE? |
| | A) | The rate of reaction = k2 [alkyl halide] [NaOCH3] |
| | B) | The reactivity order for alkyl halides (RX) is tertiary > secondary > primary. |
| | C) | The rate is independent of the leaving group. |
| | D) | The reaction occurs in a single step. |
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18 | | Which of the following statements about E1 elimination is FALSE? |
| | A) | The rate of reaction = k1 [alkyl halide] [NaOCH3]. |
| | B) | The reactivity order for alkyl halides (RX) is tertiary > secondary > primary. |
| | C) | The rate is dependent on the leaving group. |
| | D) | The reaction proceeds through a carbocation intermediate. |
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19 | | Identify the name of the mechanism for the following reaction. (13.0K) |
| | A) | E1 |
| | B) | E2 |
| | C) | SN1 |
| | D) | SN2 |
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20 | | What is the major product of the following reaction? (13.0K) |
| | A) | (14.0K) |
| | B) | (11.0K) |
| | C) | (11.0K) |
| | D) | (11.0K) |
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21 | | What is the major product formed in the following reaction? (15.0K) |
| | A) | (12.0K) |
| | B) | (12.0K) |
| | C) | (14.0K) |
| | D) | (12.0K) |
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22 | | Give all of the products expected in the following reaction. (4.0K)
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| | A) | a and c |
| | B) | a and b |
| | C) | b and c |
| | D) | b and d |
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23 | | Give the major product of the following reaction. (3.0K) |
| | A) | (2.0K) |
| | B) | (2.0K) |
| | C) | (2.0K) |
| | D) | (2.0K) |
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24 | | In the reaction of 1-chloropentane and potassium tert-butoxide, the dominant mechanism is |
| | A) | SN1. |
| | B) | SN2. |
| | C) | E1. |
| | D) | E2. |
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25 | | Reaction of 2-chloro-2-methylpentane with methanol leads to three products. Which of the following products is NOT obtained from this reaction? |
| | A) | 2-Methyl-2-pentanol |
| | B) | 2-Methoxy-2-methylpentane |
| | C) | 2-Methyl-1-pentene |
| | D) | 2-Methyl-2-pentene |
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26 | | What is the major product obtained by reaction of 2-chloro-2-methylpentane with sodium methoxide? |
| | A) | 1-Methoxy-2-methylpentane |
| | B) | 2-Methoxy-2-methylpentane |
| | C) | 2-Methyl-1-pentene |
| | D) | 2-Methyl-2-pentene |
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27 | | What is the major product from the reaction of (R)-2-bromohexane with sodium acetate in dimethylformamide? |
| | A) | 1-Hexene |
| | B) | 2-Hexene (cis and trans) |
| | C) | dl-2-Acetoxyhexane |
| | D) | (S)-2-Acetoxyhexane |
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