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9- What major product results from this reaction?
10- What is the major product of the reaction shown below?
11- What is the product of the following reaction?
12- Ozonolysis of an alkyne gave the two compounds shown below. What is the IUPAC
name of the original alkyne?
CH3CH2CH2CO2H and (CH3)3CCO2H
13- The product(s) in the following reaction is(are)
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18- Propylbenzene is subjected to the sequence of reactions below. What is the final product?
19- Identify the diene used in the reaction shown below.
20- What is the major product of the following reaction?
21- Is the proposed synthesis of cyclohexanone below likely to work? If not, why not?
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22- What would the name of this molecule be?
23- The product of this reaction would be
24- Which reagent(s) below would work best in converting 2-methyl-2-hexene to 2-methyl-3hexanol?
25- What is the major product of the following reaction?
26- What is(are) the product(s) of the following hydroboration-oxidation reaction?
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27- Rank the following in order of decreasing reactivity with bromine, Br2.
28- A compound is treated with ozone followed by zinc in water to give the following three
products. Which structure below best fits the data?
29- A compound, C7H13Cl, is reacted with sodium ethoxide and gives a single elimination
product, C7H12. Treatment with ozone followed by zinc and water gives the compound
below. Identify the original compound.
30- Identify the mechanistic pathways, respectively, for the products in the following
reaction.
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31- How would you carry out the following conversion?
32- What is the product of the reaction sequence shown below?
33- What product results from this reaction?
34- What is the IUPAC name of the following compound?
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35- What product results from this reaction?
Multiple Choice Questions:
1- Starting with toluene, which of the following is the best synthesis of meta-bromobenzoic
acid?
2- Which of the following Fischer projections corresponds to the compound shown below?
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3- Which reaction proceeds by anti addition?
4- Compound X (C7H12) is optically active. Hydrogenation of compound X gives two
isomeric 1,2-dimethylcyclopentanes, one is optically active and the other is optically
inactive. Of the following compounds, which is the only one that fits the data?
5- Which reaction below gives a pair of diastereomers?
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6- Which of the following stereoisomers gives the exclusive E2 product shown?
7- Which of the following is the 1,4-addition product in the reaction shown below?
8- Which of the following is the product of the intramolecular Diels-Alder reaction shown
below?
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9- Which of the following is an aromatic hydrocarbon?
10- Considering aromaticity, which of these would be the least acidic?