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Problem Set
1. Which compound would yield 5-keto-2-methylhexanal upon treatment with O3?

2. Which of the following reactions will produce the 2-pentyne in good yield?

3. Which of the following reactions will yield 1-butanol CH3CH2CH2CH2OH?

4. Which of the following reactions cannot produce acetamide?

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5. Which of the following compounds will produce butanone when treated with H2SO4, HgSO4 and water?

6. Which of the following compounds is aromatic?

7. Which of the following reactions will not yield benzoic acid as the major product?

8. The following stereoisomers are related as...

a. Enantiomers
b. Diasteriomers
c. Epimers
d. They are identical stereoisomers

9. What is the major product obtained from the following reaction?

10. What is the major product obtained from the following reaction?

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11. What is the number of unique cis-trans isomers possible for the following compound?
a. 2
b. 4
c. 6
d. 8

12. Which of the following reagents could be used to differentiate the following compounds by a visible change?

13. What is the major product obtained from the following reaction?

14. What is the major product obtained from the following reaction?

15. Which of the following reactions will produce isopropyl acetate in the best yield?

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16. The following compound is an example of a/an...

17. Which of the following compounds will have the highest boiling point?

18. What is the major product obtained from the following reaction?

19. What is the major product obtained from the following reaction?

20. The reason that vinyl chloride does not react with sodium hydroxide in a SN2 reaction is that...
a. hydroxide is too weak a nucleophile.
b. the sp2 carbon-chlorine bond is stronger than a sp3 carbon-chlorine bond.
c. the hydrogen atom trans to the chlorine atom sterically inhibits the substitution reaction.
d. Both answers "b" and "c" are correct.

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21. What is the major product obtained from the following reaction?

22. What is the major product obtained from the following reaction?

23. Which of the following is the strongest base?

24. What is the best name for the following compound?

a. 1,2,6-trimethylheptane
b. 2-ethyl-6-methylheptane
c. 2,6-dimethyloctane
d. 3-methyl-6-(1-methyethyl)hexane

25. What is the best name for the following compound?

a. 4-methylnaphthalene
b. 2-methylnaphthalene
c. 1-methylnaphthalene
d. 2,3-benzenetoluene

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26. What is the best name for the following compound?

a. 1,1-dimethylcyclopent-2-ene
b. 2,2-dimethylcyclopentene
c. 5,5-dimethylcyclopentene
d. 3,3-dimethylcyclopentene

27. What is the best name for the following compound?

a. E-3-isopropy-2-hexene
b. Z-3-(1-methylethyl)-2-hexene
c. cis-3-isopropy-2-hexene
d. trans-3-(1-methylethyl)-2-hexene

28. What is the best reagent to use for the following reaction?

29. What is the major product obtained from the following reaction?

30. What is the major product obtained from the following reaction?

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31. Which of the following functional groups does not contain a carbonyl group?
a. aldehydes c. ether
b. ester d. ketone

32. Which of the following compounds contains primary, secondary, tertiary, and quaternary carbons?
a. 2,2,4-Trimethylhexane c. 2-Methyl-4-ethylcyclohexane
b. Ethylcyclohexane d. 2,2-Dimethylcyclohexane

33. How many isomers of the formula C4H8Br2 are there?

a. 4 c. 8
b. 6 d. 9

34. Which of the following molecules is not a nucleophile?

a. BH3 c. HO-
b. NH3 d. H2C=CH2

35. What is the difference between the degrees of unsaturation of C6H5NO2 and C8H9Cl3?
a. 2 c. 4
b. 3 d. 5

36. Diazepam is an organic compound with 16 carbons and 11 degrees of unsaturation. If this compound also contain one chlorine,
two nitrogens, and one oxygen, what it its molecular formula?
a. C16H8ClN2O c. C16H21ClN2O
b. C16H13ClN2O d. C16H23ClN2O

37. The following compounds have similar molecular weights. Which has the highest boiling point?
a. CH3CH=O b. C2H5OH c. CH3OCH3 d. CH3CH2CH3

38. Which of the following compound pairs are constitutional isomers?

a. CH3CH2OCH3 and CH3CH2CHO c. CH3COCH2CH3 and CH3CH2COCH3
b. CH3CH2CHO and CH3CH2CH2OH d. CH3CH2CH2CHO and CH3COCH2CH3

39. Which of the following is not a nucleophile?

a. H2O b. CH3NH2 c. C2H5SH d. C6H12 (cyclohexane)

40. Which of the following is not an electrophile?

a. C2H5OC2H5 b. BF3 c. [CH3]3C(+) d. HOCl

41. In order for a reagent to behave as a nucleophile it must have

a. an overall positive charge c. a non-bonding electron pair
b. an overall negative charge d. a nitrogen or sulfur atom

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