Chapter 11 Organic Chem Wade PDF

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Chapter 11 Reactions of Alcohols 1) What series of synthetic steps could be used to carry out the transformation shown below?

Answer: 1) BH3 2) H2O2, -OH 3) PCC 2) Which alcohol reacts most rapidly with the Lucas reagent? A) benzyl alcohol B) methanol C) 2-propanol D) isobutanol Answer: A 3) Provide the structure of the major organic product in the reaction below.

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4) Provide the structure of the major organic product in the reaction below.

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5) Provide the structure of the major organic product in the reaction below.

Answer: No reaction. Tertiary alcohols are not oxidized by PCC. 6) Provide the structure of the major organic product in the reaction below.

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7) Provide the major organic product of the following reaction.

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8) Provide the name of the major organic product that results when trans-4-methylcyclohexanol is treated with Lucas reagent. Answer: a mixture of trans- and cis-1-chloro-4-methylcyclohexanes 9) Provide the reagents necessary to carry out the multistep synthesis shown below.

Answer: 1) H2SO4, Δ 2) BH3∙THF 3) H2O2, NaOH 4) PCC 10) What series of synthetic steps could be used to prepare hexan-3-ol from propan-1-ol? Answer: 1) PCC 2) CH3CH2CH2MgBr 3) H3O+ or 1) HBr or PBr3 2) Mg, Et2O 2 Copyright © 2017 Pearson Education, Inc.

3) CH3CH2CHO 11) What series of synthetic steps could be used to prepare PhCH(OH)CH2CH3 from Answer: 1) PCC 2) CH3CH2MgBr 3) H3O+ 12) What series of synthetic steps could be used to carry out the transformation shown below?

Answer: 1) PBr3 or HBr 2) Mg, ether 3) CH3CH2CHO 4) H3O+ 5) PCC or Na2Cr2O7 13) What series of synthetic steps could be used to carry out the transformation shown below?

Answer: 1) Cl2, hν 2) NaOEt, heat 3) BH3 4) H2O2, -OH 5) PCC 6) CH3MgBr 7) H2SO4, heat 14) Complete the following reaction by filling in the necessary reagents.

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15) What series of synthetic steps could be used to prepare 1-methylcyclohexanol from cyclohexene? Answer: 1) H2O, H+ or BH3; H2O2, -OH or Hg(OAc)2, H2O; NaBH4 2) Na2Cr2O7, H+ or PCC 3) CH3MgI 4) H3O+ 16) What series of synthetic steps could be used to prepare (CH3)2CHCHO from (CH3)3CH? Answer: 1) Br2, hν 2) NaOEt, heat 3) BH3 4) H2O2, -OH 5) PCC 17) What is the product of the following reaction?

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18) Provide the major organic product of the following reaction.

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19) Provide the major organic product of the following.

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20) Provide the major organic product of the following.

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21) Provide the major organic product of the following reaction.

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22) Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. TsCl, pyridine; 2. LiAlH4. Answer: cyclopentane

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23) Provide the structure of the major organic product in the reaction below. PhCH2CH2OH

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Answer: PhCH2CH2CN 24) Provide the structure of the major organic product in the reaction below.

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25) What is the final product of the reaction sequence shown below, making sure to include stereochemistry as appropriate.

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26) Provide the necessary reagents for the following conversion.

Answer: 1) TsCl, pyridine 2) LiAlD4 27) Provide the major organic product of the following.

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28) Which of the following reactions or series of reactions would reduce 3-methylbutan-2-ol into 2-methylbutane? A) 1. TsCl/pyridine 2. conc. KMnO4 B) 1. NaOCH3 2.. H2SO4/heat C) 1. pyridinium chlorochromate 2. ZnCl2/HCl D) 1. ZnCl2/HCl 2. t-butoxide/t-butanol E) 1. TsCl/pyridine 2. LiAlH4 Answer: E 29) Provide the structure of the major organic product in the reaction below.

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30) Provide the major organic product of the reaction shown.

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31) Provide the structure of the major organic product in the reaction below.

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32) Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation. (CH3)3CCH2OH + HBr → Answer:

33) Provide the structure of the major organic product in the reaction below.

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34) Which reagent would be best suited to induce the following transformation?

A) I2 B) HI C) NaI D) P / I2 Answer: D

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35) What series of synthetic steps could be used to prepare 1-bromopentane from 1bromopropane? Answer: 1) Mg, ether 2) ethylene oxide 3) HBr or PBr3 36) What series of synthetic steps could be used to carry out the transformation shown below?

Answer: 1) HBr, ROOR 2) NaCN or 1) BH3 2) H2O2, -OH 3) HBr or PBr3 4) NaCN 37) With close attention to stereochemistry, provide the major organic product for the reaction shown below.

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38) Provide a mechanism for the reaction shown below.

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39) Predict the major organic product of the following reaction.

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40) Provide the major organic product of the reaction shown.

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41) Provide a detailed, stepwise mechanism for the reaction below.

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42) Provide the major organic product of the following reaction.

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43) Draw a structure for the expected product of the reaction below.

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44 What reagents are necessary for the following conversion?

Answer: 1) Na2Cr2O7 / H2SO4 2) EtOH / acid catalyst 45) What is the best way to make the ether shown below using a Williamson Ether Synthesis reaction?

A) (CH3)3CO- + BrCH3 B) (CH3)3CBr + -OCH3 C) (CH3)3COH + BrCH3 D) (CH3)3CBr + HOCH3 Answer: A 11 Copyright © 2017 Pearson Education, Inc.

46) Show the most efficient use of the Williamson ether synthesis to prepare CH3CH2CH2OCH(CH3)2. Answer: (CH3)2CHO-Na+ + CH3CH2CH2Br 47) What series of synthetic steps could be used to carry out the transformation shown below?

Answer: 1) Hg(OAc)2, CH3CH2OH 2) NaBH4 or 1) BH3 2) H2O2, -OH 3) Na 4) CH3CH2I Note: The hydration in the second option could be accomplished with H+, H2O or Hg(OAc)2, H2O as well.

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