2. Which of the following is an intermediate in the Markovnikov addition of HBr to 2- methylcyclohexene?
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1 Quiz 7.1 Alkene Additions and Hydrohalogenations 1. Which is the most stable carbocation? 2. Which of the following is an intermediate in the Markovnikov addition of HBr to 2- methylcyclohexene? 3. What is the major product of the following reaction? Continue to next page DAT Bootcamp 1 of 13 Page
2 Quiz 7.1 Alkene Additions and Hydrohalogenations (Continued) 4. What is the major product of the following reaction? Quiz 7.2 Carbocation Rearrangements 1. Draw the major organic product generated by the following reaction: 2. What is the major product of the Markovknikov addition of HBr to the following molecule? DAT Bootcamp 2 of 13 Page
3 Quiz 7.3 How to add OH and OR to Alkenes 1. Which of the following would produce a secondary alcohol when reacted with oxymercuration-demercuration conditions? 2. Which best describes the regioselectivity and stereospecificity in the oxymercurationdemercuration of an alkene? 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. Markonikov orientation with both syn- and anti-addition 3. Which of the following reactions will lead to the formation of methoxycyclopentane as the major product? Continue to next page DAT Bootcamp 3 of 13 Page
4 Quiz 7.3 How to add OH and OR to Alkenes (Continued) 4. Which set of reagents will accomplish the following transformation? A. BH 3-THF, then H 2O 2/NaOH B. OsO 4, t-buooh C. H 3O + /CH 3OH D. Hg(OAc) 2/H 2O, then NaBH 4 E. m-cpba, then NaOCH 3 5. What is the major product of the following reaction? DAT Bootcamp 4 of 13 Page
5 Quiz 7.4 Adding Halogens to Alkenes 1. What are the major products of the following reactions? 2. What is the major product of the following reaction? 3. What is the major product of the following reaction? 4. Challenge Question: Draw the product(s) of the following reaction: DAT Bootcamp 5 of 13 Page
6 Quiz 7.5 Anti-Markovnikov Alkene Additions 1. Predict the major organic product of the following reaction: 2. What compound is the expected product upon hydrohalogenation of 2-methylpent-2-ene with peroxide and HBr? 3. What is the major organic product of the following reaction? DAT Bootcamp 6 of 13 Page
7 Quiz 7.6 Epoxides and Dihydroxylations 1. Which set of reagents will accomplish the following transformation? A. 1. H 2O 2 2. CH 3OH B. 1. (CH 3) 2S=CH 2 2. CH 3O Na + C. 1. Hg(OAc) 2/NaOH, H 2O 2 2. CH 3Li D. 1. OsO 4 2. CH 3MgBr E. 1. mcpba 2. CH 3MgBr 2. What are the major products of the following reactions? 3. Predict the major product of the following reaction: Continue to next page DAT Bootcamp 7 of 13 Page
8 Quiz 7.6 Epoxides and Dihydroxylations (Continued) 4. What reaction sequence is required to yield the product below? A. II IV III B. II I C. IV III D. III IV E. II IV I 5. Which starting material gives the product in the reaction sequence below? DAT Bootcamp 8 of 13 Page
9 Quiz 7.7 Ozonolysis 1. Please identify the missing reactant: 2. What is the structure of a compound, which has a molecular formula of C 6H 10, which upon ozonolysis and subsequent treatment with zinc and water, gives the following product? Continue to next page DAT Bootcamp 9 of 13 Page
10 Quiz 7.7 Ozonolysis (Continued) 3. What is the major organic product of the following reaction? 4. What is/are the product(s) of the following reaction? DAT Bootcamp 10 of 13 Page
11 Quiz 7.8 Catalytic Hydrogenation 1. What are the products of the following reactions? 2. Which set of reagents will accomplish the following chemical transformation? A. (1) NaNH 2, (2) CH 3Br, (3) H 3O + B. H 2, Lindlar C. Li, NH 3 D. (1) LiAlH 4, (2) H 3O + E. HgSO 4, H 2SO 4 3. Which reagent is best for preparing (Z)-4-methyl-2-hexene from 4-methyl-2-hexyne? A. H 2, Pd/C B. Na/NH 3 C. H 2NNH 2, NaOH D. Zn(Hg) / HCl E. H 2, Lindlar s catalyst (Pd/CaCO 3) DAT Bootcamp 11 of 13 Page
12 Quiz 7.9 Alkyne Addition Reactions 1. Predict the products of the following reactions: 2. Predict the products of the following reactions: DAT Bootcamp 12 of 13 Page
13 Quiz 7.10 Alkyne Hydration and Alkylation 1. Predict the products of the following reactions: 2. Predict the products of the following reactions: DAT Bootcamp 13 of 13 Page
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