19.When 2-ethylcyclohexanone is treated with catalytic base in excess D₂O, how many deuterium atoms become incorporated in the organic compound?
(A) 0
(B) 1
(C) 2
(D) 3
(E) 5

35. When 2-methylcyclohexanone is treated with catalytic base in excess D2O, how many deuterium atoms become incorporated in the organic compound? (A) 0 (B) 1 (C) 2 (D) 3 (E) 5

20. In the formation of the following ether, which reaction is preferred and why? (A) Reaction B is preferred because the oxidation step works best for primary alcohols. (B) Reaction A is preferred over reaction B because the smaller methyl iodide would make a better nucleophilic target. (C) Reaction A is preferred because the the formation of the carbocation would be stabilized in the benzylic position. (D) Reaction B would be preferred because Iodine is a better leaving group for the SN1 reaction. (E) There is no difference in these two reactions they would give approximately the same yields.

21.An unknown alkyne with a molecular formula of give the following products upon ozonolysis. What is the structure of the starting material? (A) CH3CH2CH2C≡CCH2CH3 (B) (CH3)2CHC≡CCH2(CH3)2 (C) (CH3)2CHC≡CCH2CH3 (D) CH3CH2C≡CCH2CH3 (E) CH3CH2CH2C≡CCH2CH2CH3

22. Which of the following structures could be constructed by way of a malonate ester alkylation? (A)(B)(C)(D)(E) All of the above.

23.Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting). (A) 3 ＜ 2 ＜ 4 ＜ 5 ＜ 1 (B) 2 ＜ 3 ＜ 4 ＜ 1 ＜ 5 (C) 5 ＜ 4 ＜ 3 ＜ 2 ＜ 1 (D) 2 ＜ 3 ＜ 4 ＜ 5 ＜ 1 (E) 1 ＜ 2 ＜ 5 ＜ 4 ＜ 3

24. Which of the following molecules, if isolated in its pure form, would demonstrate optical activity? (A) both IV and V (B) both I and III (C) only II (D) both III and IV (E) both I and V

25. Which of the presented mechanisms would be the most energetically favorable and thus the most likely mechanism to actually occur for the following free radical chain reaction?  (bond dissociation energies — H-H = 104 kcal/mol; Cl-Cl = 58 kcal/mol; H-Cl = 103 kcal/mol) (A)(B)(C)(D)(E)

26.Which of the final product is correct for the reactions listed below? (A) (B)(C)(D)(E)

27.Assign R or S configuration for the chiral centers in 2,3,4-trihydroxybutanal. (A) 2R, 3R (B) 2R, 3S (C) 2S, 3R (D) 2S, 3S (E) this compound is optically inactive.

28. What is the relationship between the structures shown below? (A) diastereomers (B) constitutional isomers (C) conformational isomers (D) configurational isomers (E) enantiomers

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