 |
1 |  |  What is the correct name of the following molecule?
 (12.0K) |
|  | A) | 3-hexene-1-one |
|  | B) | 5-cyclohexan-1-one |
|  | C) | 4-cycloheptenone |
|  | D) | 3-cyclohexen-1-one |
 |
 |
2 |  |  Which of the following is neither an aldehyde nor a ketone? |
|  | A) |  (13.0K) |
|  | B) |  (11.0K) |
|  | C) |  (13.0K) |
|  | D) |  (12.0K) |
 |
 |
3 |  |  What is the correct name of the following compound?
 (2.0K) |
|  | A) | 1,2-dimethylhexanone |
|  | B) | 1,3-dimethylheptanone |
|  | C) | 1,3-dimethylhexanone |
|  | D) | 3-methyl-2-heptanone |
 |
 |
4 |  |  Predict which of the following compounds will have a lower boiling point than 1-butanal. |
|  | A) | 1-butanol |
|  | B) | 2-butanol |
|  | C) | 1-butene |
|  | D) | butanoic acid |
 |
 |
5 |  |  Identify the molecule with the highest boiling point. |
|  | A) |  (11.0K) |
|  | B) |  (11.0K) |
|  | C) |  (11.0K) |
|  | D) |  (11.0K) |
 |
 |
6 |  |  What is the major product of the following reaction?
 (16.0K) |
|  | A) |  (12.0K) |
|  | B) |  (13.0K) |
|  | C) |  (11.0K) |
|  | D) |  (13.0K) |
 |
 |
7 |  |  Predict the product of the following reaction.
PhCH2OH + PCC (pyridinium chlorochromate) in methylene chloride → |
|  | A) | benzophenone |
|  | B) | benzoic acid |
|  | C) | benzaldehyde |
|  | D) | benzyl chloride |
 |
 |
8 |  |  Predict the product of the following reaction.
Cyclopentanol + PCC (pyridinium chlorochromate) → |
|  | A) | cyclopentane |
|  | B) | cyclopentanone |
|  | C) | cyclopentanaldehyde |
|  | D) | cyclopentenone |
 |
 |
9 |  |  An unknown compound on ozonolysis gives acetaldehyde and benzophenone. What is the structure of the compound? |
|  | A) | 1,2-diphenylpropene |
|  | B) | 1,1-diphenylpropene |
|  | C) | 2-phenyl-2-hexene |
|  | D) | 1,2-diphenylhexene |
 |
 |
10 |  |  Which of the following compounds is NOT oxidized by pyridinium chlorochromate (PCC)? |
|  | A) | 2-methyl-2-butanol |
|  | B) | 1-pentanol |
|  | C) | 2-pentanol |
|  | D) | 1,3-propanediol |
 |
 |
11 |  |  Which of the following sets of reaction conditions will give the product indicated?
 (13.0K) |
|  | A) | (CH3O)2Ag, heat |
|  | B) | CH3OH, HO , separate water |
|  | C) | 1) CH3ONa, 2) MeI |
|  | D) | CH3OH, H+, separate water |
 |
 |
12 |  |  What are the starting materials needed for the following reaction?
 (15.0K) |
|  | A) |  (15.0K) |
|  | B) |  (15.0K) |
|  | C) |  (15.0K) |
|  | D) |  (14.0K) |
 |
 |
13 |  |  What is the product of the following reaction?
 (12.0K) |
|  | A) |  (12.0K) |
|  | B) |  (13.0K) |
|  | C) |  (12.0K) |
|  | D) |  (13.0K) |
 |
 |
14 |  |  Predict the product of the following reaction.
 (14.0K) |
|  | A) |  (14.0K) |
|  | B) |  (14.0K) |
|  | C) |  (15.0K) |
|  | D) |  (16.0K) |
 |
 |
15 |  |  Consider the mechanism of the acid-catalyzed formation of cyclic acetals from ketones and diols:
 (14.0K) Which of the following structures does NOT represent a legitimate intermediate in this reaction? |
|  | A) |  (13.0K) |
|  | B) |  (13.0K) |
|  | C) |  (11.0K) |
|  | D) |  (14.0K) |
 |
 |
16 |  |  What is the product of the following synthesis?
 (15.0K) |
|  | A) |  (13.0K) |
|  | B) |  (13.0K) |
|  | C) |  (15.0K) |
|  | D) |  (14.0K) |
 |
 |
17 |  |  What is the product of the following reaction?
 (13.0K) |
|  | A) |  (13.0K) |
|  | B) |  (13.0K) |
|  | C) |  (13.0K) |
|  | D) |  (14.0K) |
 |
 |
18 |  |  Which of the following compounds does NOT form an imine upon reaction with an amine? |
|  | A) | benzaldehyde |
|  | B) | benzamide |
|  | C) | acetophenone |
|  | D) | benzophenone |
 |
 |
19 |  |  Which of the following compounds is an imine? |
|  | A) |  (15.0K) |
|  | B) |  (13.0K) |
|  | C) |  (13.0K) |
|  | D) |  (14.0K) |
 |
 |
20 |  |  When benzaldehyde reacts with HCN and catalytic amounts of NaCN in ethanol, the product is |
|  | A) |  (11.0K) |
|  | B) |  (12.0K) |
|  | C) |  (12.0K) |
|  | D) |  (10.0K) |
 |
 |
21 |  |  Which of the following compounds is a cyanohydrin? |
|  | A) |  (12.0K) |
|  | B) |  (12.0K) |
|  | C) |  (12.0K) |
|  | D) |  (12.0K) |
 |
 |
22 |  |  What alkyl halide and carbonyl compound is best used to prepare the following alkene using the Wittig reaction?
 (11.0K) |
|  | A) | sec-butyl bromide and propanal |
|  | B) | ethyl methyl ketone and propyl bromide |
|  | C) | ethyl bromide and 2-pentanone |
|  | D) | ethyl bromide and 3-pentanone |
 |
 |
23 |  |  What product forms when benzaldehyde is reacted with Ph3P=CH2 in diethyl ether? |
|  | A) | 1,1,2,2-tetraphenylethene |
|  | B) | acetophenone |
|  | C) | benzoyl bromide |
|  | D) | phenylethene |
 |
 |
24 |  |  What ylide is needed to make 3-ethyl-3-heptene from 3-pentanone in a Wittig reaction? |
|  | A) | Ph3P=CH-CH2-CH3 |
|  | B) | Ph3P=CH(CH2CH3)2 |
|  | C) | Ph3P=CH-CH2CH2CH3 |
|  | D) | Ph3P=CH2 |
 |
 |
25 |  |  Supply the missing reactant for the following reaction.
 (15.0K) |
|  | A) | cyclopentanone |
|  | B) | allylcyclopentane |
|  | C) | cyclopentanal |
|  | D) | cyclopentylacetone |
 |
 |
26 |  |  Which of the following is the best pair of starting materials to make 3-methyl-2-pentene via a Wittig reaction? |
|  | A) | acetaldehyde plus CH3(CH3CH2)C=PPh3 |
|  | B) | acetaldehyde plus CH3-CH=PPh3 |
|  | C) | 2-butanone plus CH3-CH=PPh3 |
|  | D) | 3-pentanone plus CH3-CH=PPh3 |
 |
 |
27 |  |  Predict the product of the following reaction.
Cyclohexanone + Pyrrolidine + Tosic acid → |
|  | A) |  (14.0K) |
|  | B) |  (14.0K) |
|  | C) |  (13.0K) |
|  | D) |  (13.0K) |
 |