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    ACS Review 15 Alcohols Diols and Thiols

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    Jana Bazzi
    This document is an ACS review covering topics related to alcohols, diols, and thiols. It contains 32 multiple choice questions testing understanding of reactions involving these functional groups, including reduction of ketones and aldehydes, oxidation and reduction reactions, Grignard reactions, and synthesis involving epoxides. The key provided indicates the correct answer to each question.

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    ACS Review 15 Alcohols Diols and Thiols

    Uploaded by

    Jana Bazzi
    106 views10 pages
    This document is an ACS review covering topics related to alcohols, diols, and thiols. It contains 32 multiple choice questions testing understanding of reactions involving these functional groups, including reduction of ketones and aldehydes, oxidation and reduction reactions, Grignard reactions, and synthesis involving epoxides. The key provided indicates the correct answer to each question.

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    Organic chemistry testbank

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    ACS Review 15 Alcohols Diols and Thiols

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    This document is an ACS review covering topics related to alcohols, diols, and thiols. It contains 32 multiple choice questions testing understanding of reactions involving these functional groups, including reduction of ketones and aldehydes, oxidation and reduction reactions, Grignard reactions, and synthesis involving epoxides. The key provided indicates the correct answer to each question.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    106 views10 pages

    ACS Review 15 Alcohols Diols and Thiols

    Uploaded by

    Jana Bazzi
    This document is an ACS review covering topics related to alcohols, diols, and thiols. It contains 32 multiple choice questions testing understanding of reactions involving these functional groups, including reduction of ketones and aldehydes, oxidation and reduction reactions, Grignard reactions, and synthesis involving epoxides. The key provided indicates the correct answer to each question.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 10
    At a glance
    Powered by AI
    The passage discusses the properties, reactions, and syntheses of alcohols, diols, and thiols including reduction of ketones to alcohols using reagents like LiAlH4 and NaBH4. It also covers oxidation and reactions with reagents like PCC and HIO4.

    Alcohols can be oxidized to aldehydes or ketones using oxidizing agents like PCC or K2Cr2O7. They also undergo reactions like cleavage with HIO4 and conversion to esters or ethers with reagents like PCC.

    NAD+ acts as an oxidizing agent, accepting electrons from other species during oxidation-reduction reactions in biological systems.

    ACS Review Alcohols Diols and Thiols

    1. Which of the following cannot be made by the reduction of a ketone or aldehyde with NaBH4 in methanol?
    A. 1-butanol
    B. 2-butanol
    C. 2-methyl-1-propanol
    D. 2-methyl-2-propanol
    2. An alcohol has the same oxidation state as a(n):
    A. ketone
    B. alkene
    C. organolithium compound
    D. alkyl halide
    3. In general, the reduction of a ketone to an alcohol can be accomplished by all of the following except one.
    Which one will not reduce a ketone?
    A. H2/Pt
    B. HIO4
    C. LiAlH4
    D. NaBH4
    4. What is the product of the following reaction?

    A. A
    B. B
    C. C
    D. D
    5. Which one of the following is not readily oxidized by K2Cr2O7 in H2SO4/H2O?
    A. n-butyl alcohol
    B. sec-butyl alcohol
    C. isobutyl alcohol
    D. tert-butyl alcohol
    6. In general, which one of the functional groups below does not react with LiAlH4?
    A. esters
    B. ketones
    C. ethers
    D. carboxylic acids
    7. Give the product of the following reaction.
    A. A
    B. B
    C. C
    D. D
    8. Which of the following reagents would be used to carry out the transformation shown below?

    A. NaBH4
    B. LiAlH4
    C. H2/Pt
    D. PCC/CH2Cl2
    9. The reaction of a Grignard reagent with ethylene oxide followed by dilute acid gives:
    A. a primary alcohol
    B. a secondary alcohol
    C. a tertiary alcohol
    D. methanol
    10. What is the product of the following reaction?

    A. CH3CH=O
    B. meso-2,3-butanediol
    C. racemic (2R,3R) and (2S,3S)-2,3-butanediol
    D. cis-2,3-epoxybutane
    11. Consider the conversion of 1-butanol to each of the compounds shown below. In which conversion is an
    oxidizing agent needed?
    A. CH3CH2CH=CH2
    B. CH3CH2CH2CH2Br
    C. (CH3CH2CH2CH2)2O
    D. CH3CH2CH2CH=O
    12. Which of the following syntheses gives 3-methyl-1-hexanol?

    A. A
    B. B
    C. C
    D. D
    13. Identify the reagent needed to carry out the following conversion.

    A. K2Cr2O7, H2SO4/H2O
    B. PCC/CH2Cl2
    C. HIO4
    D. OsO4, (CH3)3COOH, (CH3)3COH, OH-
    14. Which one of the following diols would cleave into two fragments with HIO4?
    A. 1,3-hexanediol
    B. 2,4-hexanediol
    C. 3,4-hexanediol
    D. 1,6-hexanediol
    15. Consider the structure of the AlH4¯ ion. The formal charge of Al is:
    A. -1
    B. 0
    C. +1
    D. +3
    16. As a reducing agent, NaBH4 donates a __________ to a ketone or aldehyde.
    A. proton
    B. hydrogen atom
    C. hydride ion
    D. hydrogen molecule
    17. Which of the following best describes the role of the coenzyme NAD+ (nicotinamide adenine dinucleotide)
    in biological chemistry?
    A. It reduces other species.
    B. It oxidizes other species.
    C. It catalyzes oxidation-reduction reactions.
    D. It inhibits oxidation-reduction reactions.
    18. What is the product of the synthetic sequence below?

    A. A
    B. B
    C. C
    D. D
    19. Compound A, C6H12O, is readily oxidized with K2Cr2O7 in H2SO4/H2O to give compound B, C6H10O.
    Compound B has four peaks in its C-13 NMR (broadband decoupled). Which one of the following fits the
    data for compound A?

    A. A
    B. B
    C. C
    D. D
    20. What is the final product of the following reactions?
    A. 2,3-dimethyl-3-pentanol
    B. 2,3-diemthyl-2-pentanol
    C. 2,4-dimethyl-3-pentanol
    D. 2,2-dimethyl-3-pentanol
    21. Which of the following is the ester formed between methanol and nitric acid, HNO3?

    A. A
    B. B
    C. C
    D. D
    22. The tertiary alcohol below was reacted with PCC in CH2Cl2 and gave a product, C12H12O. The product had
    a strong absorption in the IR spectrum at 1700 cm-1. Predict which of the following is the product. (Note:
    PCC is pyridinium chlorochromate, [C5H5NH+][ClCrO3¯ ].)

    A. A
    B. B
    C. C
    D. D
    23. What is the product of the reaction below?

    A. A
    B. B
    C. C
    D. D
    24. Which of the following reagents will convert cyclohexene into cis-1,2-cyclohexanediol?
    A. OsO4, (CH3)3COOH, (CH3)3COH, OH¯
    B. HIO4
    C. O3 followed by Zn/H2O
    D. CH3CO3H (peroxyacetic acid)
    25. In which of the following forms does nicotinamide adenine dinucleotide have an aromatic pyridine ring?
    A. NADH
    B. NAD+
    C. both NADH and NAD+
    D. neither NADH or NAD+
    26. Which of the synthetic procedures below would carry out the following transformation?
    A. A
    B. B
    C. C
    D. D
    27. The alcohol product(s) of the reduction of 2-methyl-3-pentanone with LiAlH4 is(are):

    A. a single enantiomer.
    B. a racemic mixture.
    C. two diastereomers.
    D. two constitutional isomers.
    28. What is the product of the following reaction sequence?

    A. A
    B. B
    C. C
    D. D
    29. Which one of the following reaction steps work best to carry out the transformation shown below?
    A. A
    B. B
    C. C
    D. D
    30. Which compound below is the product expected from the following reaction?

    A. A
    B. B
    C. C
    D. D
    31. What is the product of the reaction shown below?

    A. hexane
    B. 1-hexene
    C. 1-hexanol
    D. 2-hexanol
    32. What is the product of the following reaction sequence?

    A. cyclopentene oxide
    B. cyclopentene
    C. cyclopentane
    D. cis-1,2-cyclopentanediol
    ACS Review Alcohols Diols and Thiols KEY
    1. D
    2. D
    3. B
    4. C
    5. D
    6. C
    7. B
    8. B
    9. A
    10. B
    11. D
    12. A
    13. B
    14. C
    15. A
    16. C
    17. B
    18. C
    19. A
    20. A
    21. A
    22. C
    23. B
    24. A
    25. B
    26. D
    27. B
    28. D
    29. A
    30. C
    31. D
    32. B

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