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    ACS Review 17 Aldehydes and Ketones - Nucleophilic Addition

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    Jana Bazzi
    This document is an ACS review for aldehydes and ketones focusing on nucleophilic addition to the carbonyl group. It contains 36 multiple choice questions testing understanding of IUPAC naming, reactions involving addition, oxidation, reduction, hydration and more. Key concepts covered include carbonyl addition reactions, oxidation/reduction of alcohols, acid-catalyzed reactions of acetals/hemiacetals, Baeyer-Villiger oxidations and nucleophilic addition to carbonyls.

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    ACS Review 17 Aldehydes and Ketones - Nucleophilic Addition

    Uploaded by

    Jana Bazzi
    144 views14 pages
    This document is an ACS review for aldehydes and ketones focusing on nucleophilic addition to the carbonyl group. It contains 36 multiple choice questions testing understanding of IUPAC naming, reactions involving addition, oxidation, reduction, hydration and more. Key concepts covered include carbonyl addition reactions, oxidation/reduction of alcohols, acid-catalyzed reactions of acetals/hemiacetals, Baeyer-Villiger oxidations and nucleophilic addition to carbonyls.

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    Testbank org chem

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    This document is an ACS review for aldehydes and ketones focusing on nucleophilic addition to the carbonyl group. It contains 36 multiple choice questions testing understanding of IUPAC naming, reactions involving addition, oxidation, reduction, hydration and more. Key concepts covered include carbonyl addition reactions, oxidation/reduction of alcohols, acid-catalyzed reactions of acetals/hemiacetals, Baeyer-Villiger oxidations and nucleophilic addition to carbonyls.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    144 views14 pages

    ACS Review 17 Aldehydes and Ketones - Nucleophilic Addition

    Uploaded by

    Jana Bazzi
    This document is an ACS review for aldehydes and ketones focusing on nucleophilic addition to the carbonyl group. It contains 36 multiple choice questions testing understanding of IUPAC naming, reactions involving addition, oxidation, reduction, hydration and more. Key concepts covered include carbonyl addition reactions, oxidation/reduction of alcohols, acid-catalyzed reactions of acetals/hemiacetals, Baeyer-Villiger oxidations and nucleophilic addition to carbonyls.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 14
    At a glance
    Powered by AI
    The passage discusses IUPAC naming of aldehydes and ketones as well as common reactions such as nucleophilic addition, oxidation, reduction, hydration and more.

    Nucleophilic addition reactions to the carbonyl group are discussed including reactions with alcohols to form acetals and hemiacetals. Oxidation of alcohols to ketones and reduction of ketones are also covered.

    Common reagents mentioned include acids, alcohols, amines, peroxycarboxylic acids and hydrides used to catalyze reductions and oxidations.

    ACS Review Aldehydes and Ketones - Nucleophilic Addition to the

    Carbonyl Group
    1. What is the IUPAC name of the following compound?

    A. 3-methyl-5-heptanone
    B. 5-ethyl-3-hexanone
    C. 5-methyl-3-heptanone
    D. 2-ethyl-4-hexanone
    2. Identify the correct IUPAC name of the compound below.

    A. 4-benzyl-5-methylhexanal
    B. 5-isopropyl-5-phenylbutanal
    C. 2-methyl-3-phenylhexanal
    D. 5-methyl-4-phenylhexanal
    3. Which of the following is an acceptable IUPAC name for the compound below?

    A. o-bromo-m-chlorobenzaldehyde
    B. 6-bromo-3-chlorobenzaldehyde
    C. 2-bromo-5-chlorobenzaldehyde
    D. 1-bromo-4-chlorobenzaldehyde
    4. Which of the following has the largest Keq for the formation of the hydrate (as shown below)?
    A. A
    B. B
    C. C
    D. D
    5. The carbon-oxygen π bond of an aldehyde is formed by overlap of which two orbitals?
    A. sp-sp
    B. sp2-sp2
    C. sp2-2p
    D. 2p-2p
    6. Which of the reagents below will oxidize a secondary alcohol to a ketone?
    A. LiAlH4
    B. HIO4
    C. K2Cr2O7, H2SO4/H2O
    D. HgSO4, H2SO4/H2O
    7. Identify the reagents needed to carry out the following conversion.

    A. H2/Lindlar Pd followed by H2SO4/H2O


    B. O3 followed by H2O
    C. H2O, HgSO4/H2SO4
    D. LiA1H4 followed by H2O
    8. Which one of the following works best as the reaction steps to carry out the conversion below?
    A. A
    B. B
    C. C
    D. D
    9. Which of the following reagents would carry out the isotopic substitution reaction shown below?

    18
    A. O2/Ni (cat.)
    B. H218O/HCI (cat.)
    C. Cr18O3/pyridine
    18
    D. O3
    10. What is the product of the following reaction?

    A. 3-methylpentane
    B. 3-methyl-2-pentanol
    C. 3-methyl-2-pentene
    D. 3-methyl-1-pentyne
    11. What is the product of the reaction below?

    A. A
    B. B
    C. C
    D. D
    12. The compound shown below is the hemiacetal formed between:

    A. propanal and 2-propanol


    B. 2-methylpropanal and ethanol
    C. acetone and 1-propanol
    D. ethanal and 2-methyl-1-propanol
    13. What is the product of the reaction of butanal with excess methanol and catalytic sulfuric acid?

    A. A
    B. B
    C. C
    D. D
    14. Identify the products of the hydrolysis of the following compound.
    A. A
    B. B
    C. C
    D. D
    15. Which one of the following is not an intermediate in the acid-catalyzed reaction of benzaldehyde with 2
    equivalents of methanol to give benzaldehyde dimethyl acetal?

    A. I
    B. II
    C. III
    D. IV
    16. The compound shown below is the cyclic hemiacetal of:

    A. 5-hydroxyheptanal
    B. 5-hydroxy-2-heptanone
    C. 6-hydroxy-3-heptanone
    D. 6-hydroxyheptanal
    17. What is the product of the reaction shown?
    A. A
    B. B
    C. C
    D. D
    18. Acid-catalyzed hydrolysis of the cyclic acetal below gives:

    A. ethanal and 2-chlorocyclohexanol


    B. 1,2-ethanediol and 2-chlorocyclohexanol
    C. ethanol and 2-chlorocyclohexanol
    D. 1,2-ethanediol and 2-chlorocyclohexanone
    19. What are the products of the following reaction?

    A. cyclohexanone and ethanol


    B. cyclohexanone and ethanal
    C. 1,2-cyclohexanediol and ethanal
    D. 1,2-cyclohexanediol and ethanol
    20. The acid-catalyzed reaction of propanal with 2 equivalents of methanol forms an acetal. This can
    mechanistically be thought of as:
    A. an addition reaction followed by a substitution reaction
    B. a substitution reaction followed by an addition reaction
    C. an elimination reaction followed by a substitution reaction
    D. an addition reaction followed by an elimination reaction
    21. Which one of the following gives ethanal, CH3CH=O, (as one of two products) when added to an aqueous
    solution of HCl?
    A. A
    B. B
    C. C
    D. D
    22. Which synthetic method below correctly does the following conversion?

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

    A. 2-methyl-1-pentene
    B. 2-methyl-2-propyloxirane
    C. 4-methyl-1-pentene
    D. 1-pentene
    24. Domiodol, shown below, is used medicinally as a mucolytic agent. What are the acid-catalyzed hydrolysis
    products of Domiodol?
    A. A
    B. B
    C. C
    D. D
    25. Which of the following reacts with (CH3CH2)2NH to give the compound shown below?

    A. A
    B. B
    C. C
    D. D
    26. What is the product of the following reaction sequence?
    A. A
    B. B
    C. C
    D. D
    27. Baeyer-Villiger oxidation reactions can use peroxycarboxylic acids to convert ketones to:
    A. carboxylic acids
    B. esters
    C. epoxides
    D. α-hydroxy ketones
    28. Identify the missing reagent for the reaction below.
    A. A
    B. B
    C. C
    D. D
    29. What is the product of the following Baeyer-Villiger oxidation reaction?

    A. A
    B. B
    C. C
    D. D
    30. Which of the following is the product of the reaction between acetone, CH3COCH3, and methylamine,
    CH3NH2?
    A. A
    B. B
    C. C
    D. D
    31. Which of the following reacts with methylamine at the fastest rate?
    A. 1-pentene
    B. pentanal
    C. 2-pentanone
    D. 3-pentanone
    32. Which of the following gives the greatest percentage of hydrate (gem-diol) when dissolved in water?
    A. butanal
    B. 2,2-dichlorobutanal
    C. 3,3-dichlorobutanal
    D. 4,4-dichlorobutanal
    33. Which of the following methods can be used to synthesize 2-methyl-1-hexene, shown below, with no
    formation of isomeric by-products?
    A. A
    B. B
    C. C
    D. D
    34. Which of the following is the best method to synthesize 2-methyl-3-pentene, shown below, with little or no
    by-product formation?

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

    A. 2-methyl-1-hexene
    B. 2,3-dimethyl-2-pentene
    C. 2-methyl-2-hexene
    D. 3-methyl-1-hexene
    36. Which of the following is a hemiacetal?

    A. A
    B. B
    C. C
    D. D
    ACS Review Aldehydes and Ketones - Nucleophilic Addition to the
    Carbonyl Group KEY
    1. C
    2. D
    3. C
    4. D
    5. D
    6. C
    7. C
    8. B
    9. B
    10. A
    11. A
    12. A
    13. D
    14. A
    15. B
    16. B
    17. A
    18. D
    19. C
    20. A
    21. C
    22. C
    23. A
    24. A
    25. B
    26. D
    27. B
    28. A
    29. B
    30. A
    31. B
    32. B
    33. D
    34. C
    35. D
    36. C

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