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1 | | What is the name of the following compound? (13.0K) |
| | A) | Ethyl cyclohexyl ether |
| | B) | Hexyl propyl ether |
| | C) | 1-Ethoxycyclohexane |
| | D) | Cyclohexyl propyl ether |
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2 | | Which of the following is a secondary alcohol? |
| | A) | (12.0K) |
| | B) | (13.0K) |
| | C) | (12.0K) |
| | D) | CH3OH |
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3 | | Alcohols have higher boiling points than alkanes of comparable molecular weight because of |
| | A) | hydrogen bonding. |
| | B) | diaxial interactions. |
| | C) | steric strain. |
| | D) | hyperconjugation |
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4 | | Which of the following has the highest boiling point? |
| | A) | CH3–O–CH3 |
| | B) | CH3–CH2–OH |
| | C) | CH3–CH2–CH3 |
| | D) | CH2=CH–CH3 |
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5 | | What is the correct name for the following compound? (2.0K) |
| | A) | (R)-1-methyl-1-cyclohexen-4-ol |
| | B) | (S)-1-methyl-2-cyclohexen-4-ol |
| | C) | (R)-4-methyl-4-cyclohexen-1-ol |
| | D) | (S)-4-methyl-3-cyclohexen-1-ol |
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6 | | Which is the correct IUPAC name for the following compound? (3.0K) |
| | A) | 4-Isopropyl-1,1-dimethyl-1-pentanol |
| | B) | 5-Isopropyl-1,1-dimethyl-2-hexanol |
| | C) | 1,1,4,5-Tetramethyl-1-hexanol |
| | D) | 2,5,6-Trimethyl-2-heptanol |
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7 | | A chemist attempted unsuccessfully to form iodoethane from ethanol using NaI. Why did the reaction fail? |
| | A) | I– was not a good enough nucleophile. |
| | B) | A secondary or tertiary alcohol was needed. |
| | C) | –OH is a poor leaving group. |
| | D) | Na+ was a poor counterion. |
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8 | | What is the product of the following reaction? (15.0K) |
| | A) | (15.0K) |
| | B) | (13.0K) |
| | C) | (13.0K) |
| | D) | (12.0K) |
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9 | | Which product is obtained when (R)-2-butanol is treated with p-toluenesulfonyl chloride? |
| | A) | (R)-2-Butyl tosylate |
| | B) | (S)-2-Butyl tosylate |
| | C) | dl-2-Butyl tosylate |
| | D) | dl-2-Butanol |
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10 | | What is the leaving group in an SN2 displacement of an alkyl tosylate with sodium iodide? |
| | A) | p-toluenesulfonic acid |
| | B) | toluenesulfonate anion |
| | C) | sulfate anion |
| | D) | acetate anion |
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11 | | Give the major product of the following reaction. (13.0K) |
| | A) | (10.0K) |
| | B) | (11.0K) |
| | C) | (10.0K) |
| | D) | (11.0K) |
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12 | | What is the product of the following reaction? (14.0K) |
| | A) | (14.0K) |
| | B) | (14.0K) |
| | C) | (13.0K) |
| | D) | (14.0K) |
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13 | | What is the major product formed in the following synthesis? (16.0K) |
| | A) | (13.0K) |
| | B) | (14.0K) |
| | C) | (13.0K) |
| | D) | (14.0K) |
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14 | | Which of the following will NOT convert 1-butanol into 1-chlorobutane in one step? |
| | A) | SOCl2 |
| | B) | PCl3 |
| | C) | HCl |
| | D) | CCl4 |
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15 | | What is the first step of the mechanism for the conversion of ethanol into bromoethane using PBr3? |
| | A) | Bromide ion attacks the alcoholic carbon, displacing OH–. |
| | B) | The alcohol hydroxide group leaves, forming a carbocation. |
| | C) | The alcohol oxygen attacks phosphorus, driving out bromide ion. |
| | D) | One PBr3 bromine attacks the hydroxyl hydrogen. |
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16 | | Which reagent would be best for the conversion of tert-butanol into tert-butyl bromide? |
| | A) | PBr3 |
| | B) | HBr |
| | C) | NaBr |
| | D) | Br2, NaOH |
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17 | | Give the expected major product of the following reaction. (14.0K) |
| | A) | recovered starting material (no reaction) |
| | B) | (15.0K) |
| | C) | (15.0K) |
| | D) | (13.0K) |
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18 | | What is the major product of the following reaction? (12.0K) |
| | A) | (11.0K) |
| | B) | (11.0K) |
| | C) | (11.0K) |
| | D) | (11.0K) |
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19 | | The Williamson ether synthesis produces ethers by reacting an |
| | A) | alcohol with a metal. |
| | B) | alkoxide with a metal. |
| | C) | alkoxide with an alkyl halide. |
| | D) | alkyl halide with an aldehyde. |
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20 | | In which case would a Williamson ether synthesis fail? |
| | A) | sodium ethoxide + iodomethane |
| | B) | sodium ethoxide + iodoethane |
| | C) | sodium ethoxide + 2-iodopropane |
| | D) | sodium ethoxide + 2-iodo-2-methylpropane |
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21 | | Which of the following reagents should be used to prepare tert-butyl ethyl ether? |
| | A) | tert-butyl bromide and sodium ethoxide |
| | B) | tert-butyl alcohol and ethyl bromide |
| | C) | tert-butyl alcohol and ethanol |
| | D) | potassium tert-butoxide and ethyl bromide |
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22 | | Which of the following reagents should be used to prepare tert-butyl propyl ether? |
| | A) | 2-methylpropene and 1-propanol |
| | B) | 2-methylpropene, acetic acid and 1-propanol |
| | C) | 2-methylpropene, H2SO4 and 1-propanol |
| | D) | 1-propyl bromide and tert-butyl alcohol |
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23 | | Ethers may be used as solvents because they react only with |
| | A) | acids |
| | B) | bases |
| | C) | oxidizing agents |
| | D) | reducing agents |
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24 | | What are the products when ethyl isopropyl ether is cleaved with concentrated HI? |
| | A) | ethanol and 2-iodo-2-methylpropane |
| | B) | ethanol and 2-methylpropane |
| | C) | iodoethane and isopropyl alcohol |
| | D) | iodoethane and 2-methylpropane |
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25 | | What are the products when tert-butyl ethyl ether is cleaved with concentrated HI? |
| | A) | iodoethane and tert-butanol |
| | B) | iodoethane and 2-iodo-2-methylpropane |
| | C) | ethanol and 2-iodo-2-methylpropane |
| | D) | ethanol and tert-butanol |
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26 | | Which pair of products would result from the acid cleavage of tert-butyl propyl ether with excess concentrated HBr at an elevated temperature? |
| | A) | tert-butyl bromide and propyl alcohol |
| | B) | tert-butyl bromide and propyl bromide |
| | C) | tert-butyl alcohol and propyl bromide |
| | D) | 2-methyl-2-butene and propyl bromide |
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27 | | Which pair of products would result from the acid cleavage of phenyl propyl ether with excess concentrated HBr at an elevated temperature? |
| | A) | Phenol and 1-propanol |
| | B) | Bromobenzene and 1-propanol |
| | C) | Bromobenzene and 1-bromopropane |
| | D) | Phenol and 1-bromopropane |
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28 | | Give the expected major products of the following reaction. (13.0K) |
| | A) | recovered starting material (no reaction) |
| | B) | (13.0K) |
| | C) | (13.0K) |
| | D) | (13.0K) |
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29 | | What is the major product of the following reaction? (16.0K) |
| | A) | (17.0K) |
| | B) | (17.0K) |
| | C) | (17.0K) |
| | D) | (17.0K) |
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30 | | Which product is obtained by the acid-catalyzed ring-opening (H3O+) of cis-2,3-diethyloxirane? |
| | A) | (3R,4S)-3,4-hexanediol |
| | B) | (3R,4R)-3,4-hexanediol |
| | C) | (3R,4S)-3,4-hexanediol and (3R,4R)-3,4-hexanediol |
| | D) | (3R,4R)-3,4-hexanediol and (3S,4S)-3,4-hexanediol |
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