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1 | | What is the product of the following reaction? (15.0K) |
| | A) | (13.0K) |
| | B) | (13.0K) |
| | C) | (13.0K) |
| | D) | (13.0K) |
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2 | | Which alkene will give only optically active product upon catalytic hydrogenation (H2/Pd)? |
| | A) | (12.0K) |
| | B) | (12.0K) |
| | C) | (12.0K) |
| | D) | (12.0K) |
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3 | | What are the products formed in the following reaction? (17.0K) |
| | A) | (19.0K) |
| | B) | (19.0K) |
| | C) | (19.0K) |
| | D) | (19.0K) |
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4 | | The metal-catalyzed addition of hydrogen to an alkene occurs in what fashion? |
| | A) | syn |
| | B) | anti |
| | C) | a mixture of syn and anti |
| | D) | neither syn nor anti |
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5 | | Which of the following product(s) is(are) formed when 1,2,4-trimethylcyclopentene is hydrogenated? (16.0K) |
| | A) | I |
| | B) | I and III |
| | C) | II |
| | D) | I and IV |
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6 | | What is the major product obtained after the catalytic hydrogenation (H2/Pd) of (R)-3-methyl-1-pentene? |
| | A) | (R)-3-Methyl-pentane |
| | B) | (S)-3-Methyl-pentane |
| | C) | dl-3-Methylpentane |
| | D) | 3-Methylpentane |
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7 | | Give the major product of the following reaction. (13.0K) |
| | A) | No reaction; starting material is recovered. |
| | B) | (13.0K) |
| | C) | (13.0K) |
| | D) | (13.0K) |
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8 | | Predict the product of the following reaction.
2-octyne + H2/Pd/CaCO3 → |
| | A) | cis-2-octene |
| | B) | trans-2-octene |
| | C) | 1-octene |
| | D) | octane |
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9 | | Predict the product of the following reaction.
2-octyne + H2/Pd → |
| | A) | cis-2-octene |
| | B) | trans-2-octene |
| | C) | 1-octene |
| | D) | octane |
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10 | | Indicate the product resulting from the hydrogenation (excess H2/Pd) of 2-hexyne. |
| | A) | (Z)-2-Hexene |
| | B) | (E)-2-Hexene |
| | C) | Hexane |
| | D) | 1-Hexene |
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11 | | What are the products of the following reaction? (15.0K) |
| | A) | (14.0K) |
| | B) | (14.0K) |
| | C) | (14.0K) |
| | D) | (14.0K) |
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12 | | What starting material is needed to synthesize the following compounds? (17.0K) |
| | A) | (12.0K) |
| | B) | (11.0K) |
| | C) | (12.0K) |
| | D) | (12.0K) |
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13 | | OsO4 is often used to form diols from alkenes instead of KMnO4 for what reason? |
| | A) | It is less toxic. |
| | B) | It gives higher yields. |
| | C) | It costs less. |
| | D) | It is a colorless liquid. |
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14 | | Which of the following compounds is the potential product of the reaction of trans-2-butene and OsO4 followed by bisulfate workup? |
| | A) | (2R,3R)-2,3-butanediol |
| | B) | (2R,3S)-2,3-butanediol |
| | C) | (2S,3R)-2,3-butanediol |
| | D) | (2R)-2-hydroxybutanoic acid |
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15 | | What 10-carbon compound will undergo ozonolysis to give 2,4-pentadione as the only product? |
| | A) | 1,2-dimethylcyclopropene |
| | B) | 1,6-cyclodecadiene |
| | C) | 1,2,4,5-tetramethyl-1,4-cyclohexadiene |
| | D) | 2,4-dimethyl-1,4-cyclooctadiene |
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16 | | What is the product of the ozonolysis (O3 in CH2Cl2) of trans-3-hexene? Assume that reducing conditions (Zn/acetic acid) are used. |
| | A) | (3R,4S)-3,4-hexanediol |
| | B) | trans-2,3-Diethyloxirane |
| | C) | Propanal |
| | D) | Propanoic acid |
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17 | | How many different products are obtained upon the ozonolysis of the following C20-tetraene? (16.0K) |
| | A) | 2 |
| | B) | 3 |
| | C) | 4 |
| | D) | 5 |
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18 | | What is the product of the following reaction? (15.0K) |
| | A) | (13.0K) |
| | B) | (15.0K) |
| | C) | (15.0K) |
| | D) | (14.0K) |
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19 | | What is the product of the reaction of 3-hexyne and O3 followed by acetic acid? |
| | A) | propanoic acid |
| | B) | hexanoic acid |
| | C) | 3,4-hexanediol |
| | D) | 3-hexanone |
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20 | | How many compounds are formed upon the ozonolysis of the following triyne? (14.0K) |
| | A) | 2 |
| | B) | 3 |
| | C) | 4 |
| | D) | 5 |
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21 | | Predict the product of the following reaction. (13.0K) |
| | A) | (12.0K) |
| | B) | (14.0K) |
| | C) | (12.0K) |
| | D) | (10.0K) |
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22 | | Sharpless asymmetric epoxidation is used to convert an allylic alcohol into a chiral epoxy alcohol by using a chiral auxiliary. If 2-methyl-2-propenol is treated with tert-butyl peroxide and Ti(IV) isopropoxide in the presence of (+)-diethyl tartrate, (S)-2-hydroxymethyl-2-methyloxirane is formed. Which is the correct structure for the (S)-enantiomer? |
| | A) | (13.0K) |
| | B) | (14.0K) |
| | C) | (13.0K) |
| | D) | (13.0K) |
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23 | | Determine whether the following reaction involves substrate reduction, oxidation, or neither (i.e., no net oxidation state change of the substrate). (14.0K) |
| | A) | reduction |
| | B) | oxidation |
| | C) | neither |
| | D) | both |
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24 | | Determine whether the following reaction involves substrate reduction, oxidation, or neither (i.e., no net oxidation state change of the substrate). (12.0K) |
| | A) | reduction |
| | B) | oxidation |
| | C) | neither |
| | D) | both |
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25 | | Which species is oxidized in the following reaction?
CH3CH2OH + KMnO4 → CH3COOH |
| | A) | CH3CH2OH |
| | B) | KMnO4 |
| | C) | CH3COOH |
| | D) | This is not a redox reaction. |
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26 | | Which species is oxidized in the following reaction?
CH3CHO + LiAlH4 → CH3CH2OH |
| | A) | CH3CHO |
| | B) | LiAlH4 |
| | C) | CH3CH2OH |
| | D) | This is not a redox reaction. |
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27 | | What is the product of the following reaction? (16.0K) |
| | A) | (14.0K) |
| | B) | (15.0K) |
| | C) | (14.0K) |
| | D) | (15.0K) |
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28 | | What reagents are needed to accomplish the following transformation? (17.0K) |
| | A) | KMnO4, NaOH, H2O, heat |
| | B) | 1. | LiAlH4, Et2O | 2. | H2O, H2SO4 |
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| | C) | CrO3, HCl, pyridine |
| | D) | H2CrO4, acetone, 35˚C |
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29 | | Pyridinium chlorochromate (PCC) is a commercially available reagent that provides Cr6+ (as CrO3), and does not contain water. It is useful for oxidizing primary alcohols to aldehydes, and secondary alcohols to ketones. Which of the following compounds does NOT give an aldehyde upon reaction with PCC? |
| | A) | Benzyl alcohol |
| | B) | Cyclopentylmethanol |
| | C) | 2,2-Dimethyl-1-butanol |
| | D) | 3-Methyl-3-pentanol |
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30 | | Ozonolysis (O3 in CH2Cl2) of compound A under reducing conditions (Zn /acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H2/Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A? |
| | A) | 2,7-Dimethyl-2,8-nonadiene |
| | B) | 2,7-Dimethyl-1,8-nonadiene |
| | C) | 2,7-Dimethyl-1,6-nonadiene |
| | D) | 2,7-Dimethyl-1,7-nonadiene |
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