University of Florida

ORGO 215

Package title: Solomons Test Bank

Course Title: Solomons 11e Chapter Number: 8

1)What is the major product of the following reaction sequence?

2a. OsO₄, pyridine 2b. H₂O, NaHSO₃

OH

HO

A)

OH

HO

B)

Br

3. HO

O

+

4. H

+ enantiomer

O

5. None of these choices.

2. The most resistant compound to the action of hot alkaline KMnO₄ is:

1. Pentane
2. 1-Pentene
3. 2-Pentene
4. 2-Pentyne
5. Cyclopentene

3. What is the major product for the following reaction?

1. 
   KMnO₄, NaOH, heat
2. H3O+

HO                       OH     + enantiomer

A)

HO

HO                 +   enantiomer

B)

O

OH

HO

3. O

O

H

4. O

OH

E)

4. Which alkene would yield only CH₃CH₂COOH on oxidation with hot alkaline potassium permanganate (followed by acid work-up)?

1. (E)-2-hexene
2. (Z)-2-hexene
3. 2-methyl-2-pentene
4. (E)-3-hexene
5. (E)-4-methyl-2-pentene

5. Determine a possible structure for an alkene, X, formula C₉H₁₄, on the basis of the following information: X adds one mole of hydrogen on catalytic hydrogenation. On treatment with hot basic KMnO₄ followed by acidification, X yields the following dicarboxylic acid.

HO                 O

O                OH

I                       II                         III

IV                             V

1. I
2. II
3. III
4. IV
5. V

6. Which of the following reactions of cyclobutene would yield a meso product?

1. reaction with H₃O⁺, H₂O
2. reaction with Br₂, CCl₄
3. reaction with Cl₂, CCl₄
4. reaction with D₂, Pt
5. reaction with hot, alkaline KMnO₄, followed by acid workup

7. What reagents might be used to convert cis-2-butene into trans-2-butene?

1. 1)Br₂; 2)NaOEt, EtOH
2. 1)HBr; 2)NaOEt, EtOH
3. 1) H₃O⁺, heat; 2) NaOEt, EtOH
4. 1) H₂, Pd/C, 2) NaOEt, EtOH
5. None of these choices

8. What is the major product for the following reaction?

1. 
   O3, CH2Cl2, -78 ^oC
2. Me2S

OH

1. OH

+  enantiomer

O

HO

2. O

O

H

3. O

O

H

H

4. O
5. None of these choices.

9. An unknown compound X was subjected to ozonolysis and was found to the following products. Determine which of the following compounds listed below could be the unknown X?

1. I
2. II
3. III
4. IV
5. V

10. What is the major product for the following reaction?

1. 
   O3, CH2Cl2, -78 ^oC

CO2H

A)

SMe2

C)                  OH

2. Me2S

+  CO₂

+ enantiomer

CHO

D)

+  HCHO

E) None of these choices.

11. Which substance would undergo the following reaction?

i. O₃

?        ii. Zn, HOAc         O

H

+        H     O

1. 4-Hexen-1-yne

R

2. 3-methyl-1-hexene
3. (E)-2-hexene
4. (Z)-2-hexene
5. 4-methyl-1-pentene

12. What is the major product for the following reaction?

1. 
   O₃, CH₂Cl₂, -78 ^oC
2. Me₂S

HO

A)

O

(Racemic)

B)

O

+  CO₂

C)

O

+ HCHO

D)

E) More than one of these choices.

13. Ozonolysis of compound Z yields the products shown below. What is the structure of Z?

Z 1) O3

2) Zn, HOAc

O                 O        O

2HCH + CH₃CCH₂CH

H                   

IV                              V

1. I
2. II
3. III
4. IV
5. V

14. An alkene with the molecular formula C₁₀H₁₈ is treated with ozone and then with zinc and acetic acid. The only product isolated from these reactions is:

O

O

I                                        II                                  III

IV                                  V

1. I
2. II
3. III

4. IV
5. V

15. Consider the ozonolysis products obtained from all the unbranched and unsymmetrical

isomers of heptene. The reaction product in each case would consist of:

1. a single aldehyde.
2. an aldehyde and a ketone.
3. two different ketones.
4. two different aldehydes.
5. a single ketone.

16. An alkene adds hydrogen in the presence of a catalyst to give 3,4-dimethylhexane. Ozonolysis of the alkene followed by treatment with zinc and acetic acid gives a single organic product. The structure of the alkene is:

CH3

CH₃CH=C-CHCH₂CH₃

1. CH₃

CH3

(cis or trans)

CH₃CH₂C=CCH₃

2. CH₂CH₃

CH₃

(cis or trans)

CH₂=CCH₂CHCH₂CH₃

3. CH₃

CH2 CH₃CH₂CCHCH₂CH₃

4. CH₃

CH₃ CH₃CH₂CHCHCH=CH₂

5. CH₃

17. Compound C has the molecular formula C₇H_12. On catalytic hydrogenation, 1 mol of C absorbs 1 mol of hydrogen and yields a compound with the molecular formula C₇H₁₄. On ozonolysis and subsequent treatment with zinc and acetic acid, C yields only:

O

O

The structure of C is:

I                       II                          III

IV                             V

1. I
2. II
3. III
4. IV
5. V

18. An alkene with the molecular formula C₈H₁₆ undergoes ozonolysis to yield a mixture of (CH₃)₂C=O and (CH₃)₃CCHO. The alkene is:

1. 2,2-Dimethyl-2-hexene
2. 2,3-Dimethyl-2-hexene

3. 2,4-Dimethyl-2-hexene
4. 2,4,4-Trimethyl-2-pentene
5. More than one of these choices is a possible answer.

19. Br

    What is the major product of the following reaction sequence?

2a. KMnO₄, NaOH, heat 2b. H3O+

OH

+ enantiomer

OH

A)

O

H

H

B)                                O

O

C)

O

HO

D)

E)                O

O

OH

O

+ CO₂

20. What is the major product of the following reaction sequence?

1. t-BuOK, t-BuOH

Cl

2a. O₃, CH₂Cl₂, -78 ^oC

2b. Me₂S

O

A)

H

C)

OH

4. OH

+ HCHO

O

+ enantiomer

5. None of these choices.

21. One mole of an optically active compound, X, with the molecular formula C₆H₈ reacts with three moles of hydrogen in the presence of a catalyst to yield an optically inactive product that cannot be resolved. X also exhibits IR absorption at approximately 3300 cm^-1. Which is a possible structure for X?

1. (E)-4-hexen-1-yne
2. (Z)-4-hexen-1-yne
3. (E)-2-hexen-4-yne
4. 2-methyl-1-penten-3-yne
5. 3-methyl-1-penten-4-yne

22. What is the major product of the following reaction sequence?

2a. O₃, CH₂Cl₂, -78 ^oC

2b. Me₂S

1. OH

   OH

+  enantiomer

2. CHO

3. CO2H

D)

+   HCHO

+ CO₂

OH

E) More than one of these choices.

23. Select the structure of the major product formed in the following reaction.

2 Cl2                     ?

Cl

Cl

Cl

I                                   II

Cl

III

Cl      Cl                                 Cl

Cl

IV                                  V

1. I
2. II
3. III
4. IV
5. V

24. Select the structure of the major product formed in the following reaction.

2 HCl

?

Cl

Cl

I                                   II

Cl

Cl

III

Cl      Cl                                 Cl

Cl

IV                                  V

1. I
2. II
3. III
4. IV
5. V

25. Addition of 2 mol of HCl to 1-butyne would yield:

1. CH₃CH₂CH₂CHCl₂
2. CH₃CH₂CCl₂CH₃
3. CH₃CH₂CHClCH₂Cl

4. CH₃CH₂CH=CHCl
5. CH₃CHClCHClCH₃

26. Addition of excess HCl to 2-methyl-3-heptyne would produce: 2-methyl-3,3-dichloroheptane                          2-methyl-2,3-dichloroheptane

I                                                        II

2-methyl-4,4-dichloroheptane           2-methyl-3,4-dichloroheptane III                                               IV

2-methyl-3-chloroheptene V

1. I and II
2. I and III
3. II and IV
4. V
5. All of these choices.

27. The conversion of ethylene to vinyl bromide can be accomplished by use of these reagents in the order indicated.

A) (1) HBr; (2) NaOC₂H₅

B) (1) Br₂; (2) NaOC₂H₅

C) (1) Br₂; (2) H₂O

4. (1) NaNH₂; (2) HBr

E) (1) HBr; (2) H₂SO₄

28. What is the major product of the following reaction sequence?

1. 
   HBr (1 equiv)
2. HCl (1 equiv)

Cl

Br

A)

Br

Cl

B)

Cl    Br

C)

D)

5. None of these choices.

29. What is the major product for the following reaction?

1. 
   KMnO₄, NaOH, heat
2. H₃O⁺

1. 1. OH

B)

C)

CHO

CO₂H

+ HCHO

+ CO₂

CO2H

D)

E) None of these choices.

30. An unknown compound, A, has the molecular formula C₇H₁₂. On oxidation with hot aqueous potassium permanganate, A yields CH₃CH₂COOH and (CH₃)₂CHCOOH. Which of the following structures best represents A?

A)

B)

C)

D)

E)

31. What compound would yield an equimolar mixture of CH₃CH₂CH₂CHO and CH₃CHO upon treatment with O₃, followed by Zn/HOAc?

1. 1-Hexene
2. cis-2-Hexene
3. trans-2-Hexene
4. More than one of these choices.
5. None of these choices.

32. Which of the following could be used as the basis for a simple test that would distinguish between 1-pentyne and pentane?

1. IR examination
2. Br₂/CCl₄
3. KMnO₄/H₂O
4. Two of these choices.
5. All of these choices.

33. Which reagent or test could be used to distinguish between 3-pentyne and 1-pentyne?

1. Br₂/CCl₄
2. IR examination
3. Concd. H₂SO₄
4. KMnO₄,OH^-
5. None of these choices.

34. A reagent or test that could be used to distinguish between 1-pentene and 1-pentyne would

be:

1. Bromine in carbon tetrachloride
2. Dilute aqueous potassium permanganate
3. Chlorine in carbon tetrachloride
4. H₂SO₄
5. IR examination

35. Which of the following could be used to distinguish between 1-octyne and 3-octyne?

1. Treatment with 2 mol of HX
2. Addition of water
3. Reaction with KMnO₄
4. Decolorization of bromine in CCl₄
5. IR examination

36. 2-Pentyne will not react with:

1. H₂, Pt
2. Br₂
3. NH₃
4. H₂SO₄
5. KMnO₄/H₂O

Question type: True/False

37. The reason why anti-Markovnikov addition is seen in the hydration of alkenes using hydroboration-oxidation conditions is due to steric interactions with the boron group attaching to the less substituted carbon more easily.

38. The yields for an acid catalyzed hydration of an alkene can be increased by using dilute acid as this will help drive the equilibrium to products.

39. Due to the formation of a mercurinium ion in hydration of an alkene using oxymercuration- demercuration, we see overall anti-product form making this reaction stereospecific.

40. In halohydrin formation the reason why the halohydrin is the major product is because the solvent is more reactive that the bromide nucleophile.

41. Potassium permanganate is usually a preferred reagent for oxidative cleavage to form aldehyde, as it is a much milder and less toxic reagent than osmium tetroxide.

42) p bonds are quite susceptible to reaction with electron-seeking reagents, also referred to as

      .

43. The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is called  .

44. The introduction of a small amount of a peroxide to a hydrogen halide addition of an alkene will result in a(n)        addition where the hydrogen in the addition appears adds to the carbon with the number of hydrogens.

45. Provide a mechanistic explanation for the following observation: The same major product is obtained when 2-ethyl-1-hexene and 3-methyl-2-heptene are allowed to react with HCl.

HCl

46. Give a mechanistic explanation for the formation of the following product in significant yield. What other product(s) might also be obtained? Explain clearly.

HI                                I

47. Propose a mechanism for the following transformation accounting for the stereochemistry

in the final product:

OH

Eucalyptol

 Question type: fill-in-the-blank

48. When a reaction that could potentially yield two or more constitutional isomers instead produces only one as the major product, the reaction is said to be                                                    .

49. Hydroboration-oxidation is a reaction with       stereochemistry and        regiochemistry.

50. Predict the final product(s) obtained when (2R,3R)-2-bromo-3-methylpentane is subjected to the following sequence of reactions, briefly explaining your rationale. Provide regiochemical and stereochemical details as relevant.

NaOC₂H₅/C₂H₅OH, heat BH₃, THF

H₂O₂, OH^-

Br     H

H

NaOC₂H₅

E-3-methyl-2-hexene

H3C  H

(2R,3R)

C2H5OH

(E2: anti

elimination)

CH3

Hydroboration/oxidation: overall

Anti-Markovnikov,

syn addition of H₂O

H    OH

H3C   H

HO    H

+

H  CH3

(2S,3R)                      (2R,3S)

3-methyl-2-pentanol

51. Even when one or more stereogenic centers are produced as the result of an addition

reaction to an alkene, the product is always formed as a racemic mixture. Why is that?

52. When a particular stereoisomer reacts in such a way that it gives a particular stereoisomer as a product, even if more than one stereoisomer is theoretically possible, the reaction is said to be .

Answer: stereospecific

53. A reaction in which the reactant is not necessarily chiral but still produces primarily one stereoisomeric form of the product (or a specific subset of the possible stereoisomers) is referred to as a        reaction.

 Question type: Essay

54. Draw Fischer projection formulas of the major product of the reaction between E-2-methyl- 3-hexene and aqueous Br₂.

CH(CH₃)₂

CH(CH₃)₂

CH(CH₃)₂

CH(CH₃)₂

55. Predict the major product(s) of the following reaction, giving regiochemical and/or stereochemical details as relevant.

Br2, H2O              ?

56. Carbenes are frequently produced by a-elimination reactions. These are reactions in which the proton being lost and the leaving group are            .

57. Neutral divalent carbon compounds are called       .

58. Predict the structure of product obtained when cis-2-hexene is allowed to react with Zn/CH₂I₂.

Zn, CH I                        H                                   H

2 2

H                           + H

59. Draw Fischer projection formula(s) of the major product(s) of the reaction between Z-2- methyl-3-hexene and cold, alkaline KMnO₄.

CH(CH₃)₂             CH(CH₃)₂

60. Draw Fischer projection formula(s) of the major product(s) of the reaction between Z-3- methyl-3-hexene and cold, alkaline KMnO₄.

61. Predict the product(s) of the oxidation of 2,3,4-trimethyl-1,5-heptadiene with hot, alkaline KMnO₄.

62. Deduce the structure of an unknown compound A, C₈H₁₄, from the following data. Briefly, but clearly explain your rationale. A decolorizes Br₂/CCl₄, and upon reaction with excess H₂/Ni, affords 1-ethyl-2-methylcyclopentane. When A is subjected to ozonolysis, the following product is obtained.

O                      O

63. The “decolorization” of molecular bromine is often used as a functional group test to detect the presence of     .

64. Predict the oxidative product(s) of 2-methyl-6-octyn-2-ene after undergoing ozonolysis.

65. Devise a retrosynthetic strategy to make the epoxide shown below starting from cyclohexanol and show the forward reaction with the necessary reagents and significant intermediates.