The College at Old Westbury ORGANIC 9 Chapter 11

The College at Old Westbury

ORGANIC 9

Chapter 11.Alcohols and Ethers

Multiple Choice

Section 11.4

1)Which of the following reagent combinations give Markovnikov products?

1. 1. Oxymercuration-Demercuration

1. 2. Hydroboration-Oxidation

1. 3. 1) MMPP 2) H₃O⁺

1. 4. A and B

1. 5. A and C

1. 6. B and C

1. 7. all of the above

1. 8. none of the above

Section: 11.4

2. What is the product of the following reaction?

1. 1. I

1. 2. II

1. 3. III

1. 4. IV

Section: 11.8

3. What is the product of the following reaction?

1. 1. I

1. 2. II

1. 3. III

1. 4. IV

Section: 11.9

4. What is the product of the following reaction?

1. 1. I

1. 2. II

1. 3. III

1. 4. IV

Section: 11.9

5. What is the product of the following reaction?

1. 1. I

1. 2. II

1. 3. III

1. 4. IV

Section: 11.9, 11.10. 11.11

6. Which of the following give inversion of configuration when added to an alcohol?

1. 1. NaH, Tosyl chloride

1. 2. TBDMS-Cl, imidazole, DMF

1. 3. PBr₃

1. 4. A and B

1. 5. A and C

1. 6. B and C

1. 7. all of the above

1. 8. none of the above

Section: 11.4, 11.9, 11.11

7. What is the correct order of reagents needed for the following reaction?

1. 1. 1) Hg(OAc)₂, THF:H₂O 2) NaBH₄, OH^–3) TBDMS-Cl, imidazole, DMF 4)

Potassium tert-butoxide 5) HBr/H₂O₂ 6) TBAF/THF

1. 2. 1) Potassium tert-butoxide 2) 1 eq. HBr/H₂O₂ 3) Hg(OAc)₂, THF:H₂O 4) NaBH₄, OH^–(assume that terminalalkenes react in preference to internal alkenes)

1. 3. 1) Hg(OAc)₂, THF:H₂O 2) NaBH₄, OH^– 3) TBDMS-Cl, imidazole, DMF 4)

Potassium tert-butoxide 5) BH₃:THF 6) H₂O₂, OH^– 7)PBr₃ 8) TBAF/THF

1. 4. all of the above

Section: 11.11

8. What is the product of the following reaction?

1. 1. I

1. 2. II

1. 3. III

1. 4. IV

Section: 11.11

9. What is the correct order of reagents needed for the following reaction?

1. 1. 1) Hg(OAc)₂, THF:H₂O 2) NaBH₄, OH^–

1. 2. 1) BH₃:THF 2) H₂O₂, OH^–

1. 3. 1) Hg(O₂CCF₃)₂, THF:CH₃CH₂OH 2) NaBH₄, OH^–

1. 4. 1) MMPP 2) H⁺ 3) NaH 4) Ethyl iodide

Section: 11.14

10. What is the product of the following reaction?

1. 1. I

1. 2. II

1. 3. III

1. 4. IV

Section: 11.10. 11.14

11. What is the correct order of reagents needed for the following reaction?

1. 1. 1) Sodium Methoxide/Methanol 2) MMPP 3) NaBr

1. 2. 1) NaH, Ts-Cl 2) Sodium Methoxide/Methanol 3) MMPP 4) NaBr

1. 3. 1) NaH, Ts-Cl 2) Sodium Methoxide/Methanol 3) MMPP 4) HBr

1. 4. 1) Sodium Methoxide/Methanol 2) MMPP 3) HBr

Section: 11.4, 11.5

12. Which of the following reagent combinations, when added to an alkene, give regiospecific and stereospecific products?

1. 1. Oxymercuration-Demercuration

1. 2. Hydroboration-Oxidation

1. 3. 1) MMPP 2) H₃O⁺

1. 4. A and B

1. 5. A and C

1. 6. B and C

1. 7. all of the above

1. 8. none of the above

Section: 11.13, 11.14, 11.15

13. Which of the following reagent combinations give Markovnikov products?

1. 1. 1) MMPP 2) HBr

1. 2. 1) MMPP 2) NaBr

1. 3. 1) MMPP 2) H₃O⁺

1. 4. A and B

1. 5. A and C

1. 6. B and C

1. 7. all of the above

1. 8. none of the above

Section: 11.15

14. What is the correct order of reagents needed for the following reaction?

1. 1. KMnO₄, OH^–, H₂O, cold

1. 2. 1) OsO₄, pyridine 2) NaHSO₃, H₂O

1. 3. 1) MMPP 2) H₃O⁺

1. 4. all of the above

1. 5. none of the above

Section: 11.16

15. Crown ethers are examples of phase-transfer catalysts (PTC). PTC takes the ionic nucleophile and brings it into the organic layer. There they pick up the leaving group anion and bring it back into the aqueous layer. The leaving group is transferred for another nucleophile and the whole process continues. PTC allows SN2 reactions to occur in the best possible solvent,                                                                                  .