University of New England CHEM 1020 Chapter 9 -- Aldehydes and Ketones MULTIPLE CHOICE 1)The common name for the following molecule is:             acetaldehyde dimethyl aldehyde ethyl ketone formaldehyde methylmethanal                                    What is the structure of cyclohexanecarbaldehyde?             D) E)                                                         C)                                      The IUPAC name for ethyl methyl ketone is 2-butanone 2-pentanone 3-pentanone propanone acetophenone                                    The IUPAC name for the following molecule is:             3-ethyl-1-phenyl-3-pentenone 3-ethyl-5-phenyl-2-penten-4-one allyl benzyl ketone (E)-3-ethyl-1-phenyl-3-penten-2-one (Z)-3-ethyl-1-phenyl-3-penten-2-one                                    What is the class of compound produced from the reaction of a ketone with hydrazine? oxime amide hydrazone semicarbazone imide                                    Which of the following molecules is a hemiacetal? D) E)         C)                                      Which of the following compounds is a hemiacetal? D)                                                                     E) C)                                        Which of the following compounds is a cyanohydrin? D)           E) C)                                          Which of the following is a hydrazone? A)   B) C)       D)   E)                                          The name of the following is:   2-hydroxy-4-pentanone

University of New England

CHEM 1020

Chapter 9 -- Aldehydes and Ketones

MULTIPLE CHOICE

1)The common name for the following molecule is:

1. 1. acetaldehyde
   2. dimethyl aldehyde
   3. ethyl ketone
   4. formaldehyde
   5. methylmethanal

2. What is the structure of cyclohexanecarbaldehyde?
   1. 
      D)
   2. E)

3. The IUPAC name for ethyl methyl ketone is
   1. 2-butanone
   2. 2-pentanone
   3. 3-pentanone
   4. propanone
   5. acetophenone

4. The IUPAC name for the following molecule is:

1. 1. 3-ethyl-1-phenyl-3-pentenone
   2. 3-ethyl-5-phenyl-2-penten-4-one
   3. allyl benzyl ketone
   4. (E)-3-ethyl-1-phenyl-3-penten-2-one
   5. (Z)-3-ethyl-1-phenyl-3-penten-2-one

5. What is the class of compound produced from the reaction of a ketone with hydrazine?
   1. oxime
   2. amide
   3. hydrazone
   4. semicarbazone
   5. imide

6. Which of the following molecules is a hemiacetal?
   1. D)

1. 2. E)

C)

7. Which of the following compounds is a hemiacetal?
   1. D)

1. 2. 
      E)

C)

8. Which of the following compounds is a cyanohydrin?
   1. D)

1. 2. E)

C)

9. Which of the following is a hydrazone?

A)

B)

C)

D)

E)

10. 
    The name of the following is:

1. 1. 2-hydroxy-4-pentanone.
   2. 2-oxo-4-pentanol.
   3. 4-oxo-2-pentanol.

1. 4. 1-acetyl-2-propanol.
   5. 4-hydroxy-2-pentanone.

11. Which of the following molecules has the highest boiling point?
    1. o-xylene
    2. m-xylene
    3. p-xylene
    4. benzaldehyde
    5. benzyl alcohol

12. Which of the following aldehydes can exist in equilibrium with a cyclic hemiacetal?
    1. 4-pentenal
    2. 3-hydroxypropanal
    3. 2-hydroxybutanal
    4. 3-hydroxybutanal
    5. 4-hydroxybutanal

13. What class of compound most closely resembles an acetal in its reactivity with CH₃MgBr?
    1. ethers
    2. aldehydes
    3. ketones
    4. alcohols
    5. thiols

14. In a carbonyl group
    1. the oxygen acts as a Lewis acid.
    2. the C=O bond length is shortened due to resonance.
    3. the carbon is sp³ hybridized.
    4. the carbon is nucleophilic and the oxygen is electrophilic.
    5. the carbon is electrophilic and the oxygen is nucleophilic.

15. The expected order of boiling points of the following is:

A) 3>2>1

B) 2>1>3

C) 2>3>1

D) 1>2>3

E) 1>3>2

16. Which of the hydrogens in the following molecule are most acidic? The hydrogens on carbon

1. 1. 1
   2. 2
   3. 3
   4. 4
   5. 5

17. The equilibrium that exists between the keto and enol forms of aldehydes and ketones is known as:
    1. stereoisomerism
    2. configurational isomerism
    3. geometric isomerism
    4. tautomerism
    5. positional isomerism

18. The number of a-hydrogens in                                  is:
    1. 1
    2. 3
    3. 4
    4. 8
    5. 14

19. The predominant product from the reaction below is:

1. 1. 
      D)

1. 2. 
      E)

20. The enol tautomer of 3-pentanone is:
    1. D)

1. 2. E)

C)

21. Which hydrogens in the following compound will be exchanged most rapidly for deuterium upon reaction with D₂O and NaOD?

1. 1. H₁
   2. H₂
   3. H₃
   4. H₄
   5. H₅

22. In the mechanism for acid catalyzed hemiacetal formation, the first step is:
    1. protonation of the carbonyl oxygen
    2. nucleophilic attack at the carbonyl carbon
    3. protonation of the oxygen of the alcohol
    4. nucleophilic attack at the carbon of the alcohol
    5. elimination of a water molecule

23. The second step in the base catalyzed aldol condensation is:
    1. formation of the enolate ion
    2. addition of an enolate to a carbonyl group
    3. protonation of the alkoxide ion
    4. protonation of the carbonyl oxygen
    5. loss of a proton from the ? carbon

24. What statement is false relative to the nucleophilic additions?
    1. When a weak nucleophile is present, the reaction can be catalyzed by acid.
    2. The nucleophile attacks the trigonal carbon of the carbonyl group.
    3. Ketones are more reactive than aldehydes.
    4. Nucleophiles that add irreversibly are poor leaving groups.
    5. Nucleophiles can be classified as those that add reversibly to carbonyl compounds and those that add irreversibly.

25. Which statement about the mechanism of imine formation from a primary amine and an aldehyde or ketone is false?
    1. The first steps involve addition of the amine to the carbonyl carbon to form a tetrahedral intermediate.
    2. The last steps involve elimination of water to form a carbon-nitrogen p-bond.
    3. All steps are reversible.
    4. The reaction involves S_N2 displacement of the carbonyl oxygen by the amine nitrogen.
    5. The reaction does not require a strong acid catalyst.

26. Which of the following nucleophiles add reversibly to a carbonyl group?

1. 1. I, II and IV
   2. II
   3. I and II
   4. III and IV

1. 5. I, II, III and IV

27. What type of compound is produced from the following reaction?

1. 1. an amide
   2. an alcohol
   3. an acid
   4. an aldehyde
   5. a ketone

28. An oxime can be produced by the reaction of an aldehyde and:
    1. hydroxylamine
    2. hydrazine
    3. methylamine
    4. phenylhydrazine
    5. semicarbazide

29. Which of the following compounds will not act as a nucleophile in an Aldol reaction?

A)

B)

C)

4. HCHO
5. C and D

30. What reaction will produce the following product?

A)

B)

C)

D)

E)

31. The reaction of a Grignard reagent with acetone followed by acid hydrolysis will produce what type of product?
    1. a primary alcohol
    2. a secondary alcohol
    3. a tertiary alcohol
    4. a carboxylic acid
    5. a ketone

32. Which reagents would you use to accomplish the following conversion?

1. 1. NaBH₄, H₂O
   2. LiAlH₄, ether; then H₃O⁺
   3. H₂, Pt
   4. all of these
   5. none of these

33. Which of the following reactions will produce a cyanohydrin?

A)

B)

C)

D)

E)

34. What Grignard reagent and carbonyl compound react to give benzyl alcohol after treatment with aqueous acid?
    1. phenyl magnesium bromide and formaldehyde
    2. phenyl magnesium bromide and oxirane
    3. benzaldehyde and methyl magnesium bromide
    4. benzaldehyde and ethyl magnesium chloride
    5. acetophenone and methyl magnesium chloride

35. Which reagent will accomplish the following transformation?

1. 1. NaOH
   2. CrO₃, H₂SO₄
   3. CH₃MgBr
   4. NaBH₄
   5. H₂, Pd

36. What is the structure of the aldol produced from reacting propanone with NaOH?

B)

C)

D)

E)

37. 
    What reactants give the following molecule upon acid hydrolysis?

1. 1. cyclohexyl magnesium bromide and acetaldehyde
   2. cyclohexanol and
   3. cyclohexanone and
   4. cyclohexanecarbaldehyde and
   5. cyclohexanone and ethenyl magnesium bromide

38. The products from                                                                    are:

A)

B)

C)

E) no reaction

39. can be prepared from:

A)

B)

C)

E)

40. The product from                                                                         is:

A)

B)

D)

E)

41. Which of the following compounds will give a positive silver mirror test (Tollens' test)?
    1. D)

1. 2. E)

C)

42. The aldol obtained by treating                                                 with base is:

A)

B)

C)

D)

E)

43. The major product obtained from                                                                                    is:

1. 1. 
      D)
   2. E)

44. A reaction sequence that will accomplish the transformation below is:

1. 1. 1. CH₃MgBr 2. H₃O⁺
   2. 1. CH₃Li 2. H₃O⁺ 3. CrO₃, H₂SO₄
   3. 1. LiAlH₄ 2. H₃O⁺ 3. CH₃MgBr
   4. 1. H₂, Pd catalyst 2. CH₃MgBr 3. H₃O⁺
   5. 1. CrO₃, H₂SO₄ 2. CH₃MgBr 3. H₃O⁺

45. The organic product of the reaction                                                                             is:

1. 1. D)