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1. Which of the following is a substitution reaction? A) I B) II C) III D) IV 2. Consider the following S N 2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of 1-chloro-3methylbutane is doubled?
A) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) It would reduce by half
3. For the reaction sequence below, identify the expected major product(s). A) I B) II C) III D) I and III E) II and III 4. Which of the alkenes shown below would produce a chirality center upon Markovnikov
hydrohalogenation? A) B) C) D) E) 5. For the following dihydroxylation reaction which of the following statements is correct
regarding the expected products? A)
B)
C)
D)
E) Equal amounts of I and II produced
Equal amounts of III and IV produced
Equal amounts of I and IV produced
Equal amounts of II and III produced
Equal amounts of I and III produced 6. Which of the following alkyl halides is essentially unreactive in an S N 2 reaction? A) I B) II C) III D) IV E) V 7. Rank the following compounds from most to least reactive in an S N 2 reaction. A)
B)
C)
D)
E) Igt;IVgt;IIgt;III
IIgt;Igt;IVgt;III
IIIgt;IVgt;Igt;II
Igt;IIIgt;IIgt;IV
IVgt;IIIgt;Igt;II 8. Which of the following correctly describes the product(s) of the reaction below? A)
B)
C)
D) Only one stereoisomer
An equal mixture of enantiomers
A roughly equal mixture of diasteromers
A roughly equal mixture of constitutional isomers 9. Predict the product(s) for the following reaction. A) Both I amp; IV B) II C) III D) IV E) Both II amp; III 10. Viridenomycin, shown below, is a polyene antibiotic that displays anti-tumor activity. Its
structural complexity and chemical instability have made it a challenging target for
organic chemists to synthesize. Ignoring the benzene ring, how many disubstituted Z
alkenes are present in viridenomycin? A. 1 B. 2 C. 3 D. 4 11. Rank the following from most to least stable. A) A, B, C B) C, B, A C) B, C, A D) B, A, C 12. Draw the major product of the following reaction. A B C D 13. Which of the following is a reasonable definition of a concerted reaction?
A) it is a reaction in which bond breaking occurs first
B) it is a reaction in which all bond-breaking and bond-forming occurs at the same time
C) it is a reaction in which bond forming occurs first
D) it is a substitution reaction
14. Which of the following is the strongest nucleophile? 15. In an addition reaction to an alkene, the π bond plays the role of:
A)
D) nucleophile
A and B B)
E) electrophile
B and C C) leaving group 16. The regioselectivity and stereospecificity in hydrohalogenation of an alkene is best described
as:
A)
Markovnikov orientation with syn-addition
B)
Markovnikov orientation with anti-addition
C)
anti-Markovnikov orientation with syn-addition
D)
anti-Markovnikov orientation with anti-addition
E)
Markovnikov orientation with both syn- and anti-addition 17. What is the expected major product for the following reaction? A) I B) II C) III D) IV E) V 18. Which of the following is the energy diagram for the following reaction? 19. Which of the following is the structure of the rearranged carbocation intermediate in the
following dehydration? 20. Which of the given reaction schemes would produce the molecule shown below? A)
D) Both A and B B)
E) Both B and C C) 21. Which of the following is the major product of the reaction shown? A) I B) II C) III D) IV 22. What is (are) the expected major product(s) for the following reaction sequence? A) I B) II C) III D) I and II E) I and III 23. Identify the major organic product generated from the reaction shown. A)
B)
C)
D) I
II
III
IV 24. For the reaction sequence below, identify the expected major products. A) B) C) D) 25. What is the expected major product of the reaction sequence shown below? A) I B) II C) III D) IV E) V 26. What is the expected major product for the following reaction? A) B) D) E) C) 27. What is the IUPAC name for the following compound? A) 3-Fluorobutane B) 2-Fluorobutane C) (S)-2-Fluorobutane D) (R)-2-Fluorobutane 28. What is the expected major product of the following reaction sequence? A) I B) II C) III D) IV E) V 29. What is the expected major product of the following reaction sequence? A) I B) II C) III D) IV E) V 30. What is the expected major product of the following reaction sequence? A) D) B) E) C)
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