Organic Chemistry 4th 4th Janice Smith Test Bank

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Organic Chemistry 4th 4th Janice Smith Test Bank

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INSTANT DOWNLOAD WITH ANSWERS
Organic Chemistry 4th 4th Janice Smith TB

Chapter 2: Acids and Bases

 

1. Which of the following statements is a correct definition for a Brnsted-Lowry acid?
  A) Proton acceptor C) Electron pair acceptor
  B) Electron pair donor D) Proton donor

 

2. Which of the following statements about a Brnsted-Lowry base is true?
  A) The net charge may be zero, positive, or negative.
  B) All Brnsted-Lowry bases contain a lone pair of electrons or a p bond.
  C) All Brnsted-Lowry bases contain a proton.
  D) The net charge may be zero or positive.

 

3. Which of the following compounds is both a Brnsted-Lowry acid and base?

 

  A)  I, II    B)  I, III    C)  II, IV    D)  I, IV

 

4. Which of the following species cannot act as both a Brnsted-Lowry acid and base?
  A)  HCO3    B)  HSO4    C)  HO    D)  H2PO4

 

5. Which of the following species is not a Brnsted-Lowry base?
  A)  BF3    B)  NH3    C)  H2O    D)  PO43-

 

6. Which of the following statements about Brnsted-Lowry acids and bases is true?
  A) Loss of a proton from a base forms its conjugate acid.
  B) Loss of a proton from an acid forms its conjugate base.
  C) Gain of a proton by an acid forms its conjugate base.
  D) Brnsted-Lowry acid-base reactions always result in the transfer of a proton from a base to an acid.

 

7. Which of the following species is the conjugate base of methanol, CH3OH?
  A)  CH3OH2+    B)  CH3O    C)  CH3    D)  CH4

 

8. Which of the following species is the conjugate base of the hydronium ion, H3O+?
  A)  H3O    B)  H2O    C)  H2O    D)  HO

 

9. Which of the following species is the conjugate acid of ammonia, NH3?
  A)  H4N    B)  H3N+    C)  H2N    D)  H4N+

 

10. Which is the conjugate acid in the following reaction?

 

  A)  I    B)  II    C)  III    D)  IV

 

11. Which is the conjugate base in the following reaction?

 

  A)  I    B)  II    C)  III    D)  IV

 

12. Which is the conjugate acid in the following reaction?

 

  A)  I    B)  II    C)  III    D)  IV

 

13. Which is the conjugate base in the following reaction?

 

  A)  I    B)  II    C)  III    D)  IV

 

14. Which of the following statements about acid strength is true?
  A) The stronger the acid, the further the equilibrium lies to the left.
  B) The stronger the acid, the smaller the Ka.
  C) The stronger the acid, the larger the pKa.
  D) The stronger the acid, the smaller the pKa.

 

15. Which of the following compounds is the strongest acid?

 

  A)  I    B)  II    C)  III    D)  IV

 

16. Which of the following compounds is the strongest acid?
  A)  CH3OH    B)  BrCH2OH    C)  CH3NH2    D)  CH3Cl

 

17. Which of the following compounds is the weakest acid?
  A)  HF    B)  HCl    C)  HBr    D)  HI

 

18. Which of the following compounds is the weakest acid?
  A)  H2S    B)  PH3    C)  HCl    D)  SiH4

 

19. Which of the following species is the strongest base?
  A)  HO    B)  H2N    C)  CH3COO    D)  Cl

 

20. Which of the following ranks the compounds in order of increasing basicity, putting the least basic first?
  A) CH3NH2 < CH3OH < CH4 C) CH4 < CH3NH2 < CH3OH
  B) CH3OH < CH3NH2 < CH4 D) CH4 < CH3OH < CH3NH2

 

21. Consider the following molecule with protons labeled, I-III.  Rank these protons in order of decreasing acidity, putting the most acidic first.

 

  A)  I > II > III    B)  I > III > II    C)  III > II > I    D)  III > I > II

 

22. Rank the following compounds in order of increasing acidity, putting the least acidic first.

 

  A) III < I < IV < II C) II < I < IV < III
  B) III < IV < I < II D) III < I < II < IV

 

23. Rank the following compounds in order of increasing acidity, putting the least acidic first.

 

  A) I < IV < III < II C) II < III < IV < I
  B) I < III < IV < II D) II < IV < III < I

 

24. Rank the following compounds in order of decreasing acidity, putting the most acidic first.

 

  A) IV > II > III > I C) I > II > IV > III
  B) III > II > IV > I D) III > IV > II > I

 

25. Rank the following compounds in order of decreasing acidity, putting the most acidic first.

 

  A) IV > II > III > I C) III > IV > II > I
  B) IV > III > II > I D) III > IV > I > II

 

26. Rank the following conjugate bases in order of increasing basicity, putting the least basic first.

 

  A)  II < I < III    B)  II < III < I    C)  I < II < III    D)  I < III < II

 

27. Rank the following conjugate bases in order of decreasing basicity, putting the most basic first.

 

  A)  II > I > III    B)  I > II > III    C)  III > I > II    D)  III > II > I

 

28. Which of the following is the strongest base?
  A)  CH3COCH3    B)  CH3COOH    C)  NH3    D)  H2O

 

29. What is the direction of equilibrium when acetylene (C2H2) reacts with H2N in an acid-base reaction?

 

  A)  Left    B)  Right    C)  Neither    D)  Cannot be determined

 

30. What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide (CH3CH2O) in an acid-base reaction?

 

  A)  Left    B)  Right    C)  Neither    D)  Cannot be determined

 

31. Which of the following statements explain why H2O is a stronger acid than CH4?
  A) H2O can form hydrogen bonds while CH4 cannot.
  B) H2O forms a less stable conjugate base, HO.
  C) CH4 forms a more stable conjugate base, CH3.
  D) H2O forms a more stable conjugate base, HO.

 

32. Which of the following statements explain why HBr is a stronger acid than HF?
  A) Br is more stable than F because Br is larger than F.
  B) Br is less stable than F because Br is larger than F.
  C) Br is more stable than F because Br is less electronegative than F.
  D) Br is less stable than F because Br is less electronegative than F.

 

33. Which of the following compounds has the lowest pKa?
  A)  H2O    B)  H2S    C)  NH3    D)  CH4

 

34. Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH3COOH) and ethanol (CH3CH2OH)?
  A)  Hybridization    B)  Electronegativity    C)  Resonance    D)  Size

 

35. Which of the following concepts can be used to explain the difference in acidity between acetylene (C2H2) and ethylene (C2H4)?
  A)  Size    B)  Resonance    C)  Inductive effect    D)  Hybridization

 

36. Which of the following concepts can be used to explain the difference in acidity between ethanol (CH3CH2OH) and 2-fluoroethanol (FCH2CH2OH)?
  A)  Size    B)  Inductive effect    C)  Resonance    D)  Hybridization

 

37. Rank the following compounds in order of decreasing acidity, putting the most acidic first.

 

  A)  I > II > III    B)  III > II > I    C)  II > III > I    D)  III > I > II

 

38. Which of the following statements about Lewis acids is true?
  A) Lewis acids are proton donors.
  B) Lewis acids are proton acceptors.
  C) Lewis acids are electron pair donors.
  D) Lewis acids are electron pair acceptors.

 

39. Which of the following statements about Lewis bases is true?
  A) Lewis bases are electron pair acceptors.
  B) Lewis bases are electron pair donors.
  C) Lewis bases are proton donors.
  D) Lewis bases are proton acceptors.

 

40. Which of the following is a Lewis acid but not a Brnsted-Lowry acid?
  A)  CH3OH    B)  H2O    C)  CH3COOH    D)  BF3

 

41. Which of the following species can be both Lewis acid and Lewis base?

 

  A)  I, III, IV    B)  I, II, IV    C)  II, III, IV    D)  I, II, III

 

42. What is the correct classification of the following compound?

 

CH3-O-CH3

  A) Brnsted-Lowry acid and Lewis acid. C) Brnsted-Lowry base.
  B) Brnsted-Lowry base and Lewis base. D) Lewis base.

 

43. Identify the Lewis acid in the following reaction.

 

  A)  I    B)  II    C)  III    D)  IV

 

44. Identify the Lewis base in the following reaction.

 

  A)  I    B)  II    C)  III    D)  IV

 

45. Which of the following compounds is not a Lewis acid?
  A)  AlCl3    B)  HCl    C)  H2O    D)  CBr4

 

46. What is the role of methylchloride (CH3Cl) in the following reaction?

 

  A) Lewis acid C) Brnsted-Lowry acid
  B) Lewis base D) Brnsted-Lowry base

 

47. What is the electrophilic site in the following compounds?

 

  A) I = Carbon; II = carbon; III = boron. C) I = Carbon; II = oxygen; III = boron.
  B) I = Chlorine; II = carbon; III = boron. D) I = Carbon; II = carbon; III = fluorine.

 

48. What is the nucleophilic site in the following compounds?

 

  A) I = Hydrogen; II = p electrons in bond; III = nitrogen.
  B) I = Oxygen; II = carbon; III = nitrogen.
  C) I = Hydrogen; II = carbon; III = carbon.
  D) I = Oxygen; II = p electrons in bond; III = nitrogen.

 

 

Answer Key

 

1. D
2. B
3. B
4. C
5. A
6. B
7. B
8. C
9. D
10. C
11. D
12. D
13. C
14. D
15. D
16. B
17. A
18. D
19. B
20. D
21. C
22. B
23. A
24. D
25. B
26. A
27. C
28. C
29. B
30. A
31. D
32. A
33. B
34. C
35. D
36. B
37. D
38. D
39. B
40. D
41. A
42. B
43. B
44. A
45. D
46. B
47. A
48. D

Chapter 12: Oxidation and Reduction

 

1. Which of the following statements about oxidation and reduction is not true?
  A) The conversion of an alkyne to an alkene is reduction.
  B) The conversion of an alkene to an alkane is reduction.
  C) Oxidation results in a decrease in the number of C-H bonds.
  D) Reduction results in an increase in the number of C-Z bonds.

 

2. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

3. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

4. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

5. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

6. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

7. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

8. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

9. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

10. What is the correct classification of the following reaction?
  A) Reduction reaction C) Elimination reaction
  B) Oxidation reaction D) Substitution reaction

 

11. Rank the following compounds in order of increasing oxidation level (from lowest to highest).

 

  A) I < III < II < IV C) IV < I < III < II
  B) II < III < I < IV D) II < IV < III < I

 

12. What happens to the carbon atom in the transformation of chloromethane to methyllithium?

 

CH3Cl     +     2Li          CH3Li     +     LiCl

  A) Oxidized C) Oxidized and Reduced
  B) Reduced D) Neither oxidized nor reduced

 

13. Rank the following compounds in order of decreasing oxidation level, putting the compound with the highest oxidation level first.

 

  A) II > IV > I > III C) III > I > II > IV
  B) I > III > IV > II D) III > I > IV > II

 

14. Which of the following classes of organic compounds cannot undergo reduction easily?
  A)  Alkanes    B)  Alkenes    C)  Alkynes    D)  Carboxylic acids

 

15. Determine the product(s) of the following reaction.
  A)  I and III    B)  II and III    C)  I, II, III    D)  I or II

 

16. Rank the following alkenes in order of decreasing heat of hydrogenation.
  A)  I > II > III    B)  III > I > II    C)  II > I > III    D)  III > II > I

 

17. Which of the following explains why heats of hydrogenation cannot be used to determine the relative stability of compounds A and B below?
  A) Compound A is trisubstituted while compound B is monosubstituted.
  B) Compound A has E configuration while compound B has no E/Z configuration.
  C) Both compounds A and B have no E/Z configurations.
  D) Hydrogenation of A and B give different alkanes.

 

18. Rank the following alkenes in order of increasing rate of hydrogenation.
  A) I < III < IV < II C) I < II < III < IV
  B) IV < III < II < I D) IV < II < III < I

 

19. A compound X of molecular formula C8H12 with no triple bonds reacts with one equivalent of H2 to give a new compound having molecular formula C8H14.  What can be inferred about the structure of compound X?
  A) Compound X has 3 rings.
  B) Compound X has 3 p bonds.
  C) Compound X has 1 ring and 2 p bonds.
  D) Compound X has 2 rings and 1 p bond.

 

20. Determine the product of the following reaction.
  A)  I    B)  II    C)  III    D)  IV

 

21. What reagent is required to accomplish the following transformation?
  A)  Na, NH3    B)  H2, Pd-C    C)  H2, Ni    D)  H2, Lindlar catalyst

 

22. What reagent is required to accomplish the following transformation?
  A)  Na, NH3    B)  H2, Pd-C    C)  H2, Ni    D)  H2, Lindlar catalyst

 

23. What is the starting material in the following reaction?
  A)  I    B)  II    C)  III    D)  IV

 

24. Determine the product of the following reaction.
  A)  I    B)  II    C)  III    D)  IV

 

25. Which of the following statements about the reduction of epoxides with LiAlH4 is true?
  A) The nucleophile is a hydride (H).
  B) In unsymmetrical epoxides, nucleophilic attack of H occurs at the more substituted carbon atom.
  C) The reaction follows SN1 mechanism.
  D) The nucleophile, H, is a weak nucleophile.

 

26. Which is (are) the product(s) of the following reaction?
  A)  Only I and II    B)  Only I and III    C)  Only II and III    D)  I, II, III

 

27. Which of the following products do not form in the following reaction?

 

  A)  Only I    B)  Only II    C)  Only III and IV    D)  Only I and II

 

28. What is (are) the product(s) of the following reaction?

 

  A)  Only I    B)  Only II    C)  Only III    D)  Only I and II

 

29. Determine the product of the following reaction, ignoring stereochemistry.

 

  A)  I    B)  II    C)  III    D)  IV

 

30. What is (are) the product(s) of the following reaction?
  A)  I    B)  II    C)  III    D)  IV

 

31. What is the reagent required to accomplish the following transformation?
  A) LiAlH4 C) RCO3H, H2O/HO
  B) [1] OsO4; [2] NaHSO3, H2O D) PCC/CH2Cl2

 

32. What is the reagent required to accomplish the following transformation?
  A) [1] OsO4; [2] NaHSO3, H2O C) RCO3H/H2O/HO
  B) KMnO4, H2O/HO D) PCC/CH2Cl2

 

33. Determine the product of the following reaction.
  A)  I    B)  II    C)  III    D)  IV

 

34. After ozonolysis and treatment of the unstable ozonide with CH3SCH3, compound A was converted to the compound below.  What is the structure of compound A?
  A)  I    B)  II    C)  III    D)  IV

 

35. What is the starting material in the following sequence of reactions?
  A)  I    B)  II    C)  III    D)  IV

 

36. Which of the following is (are) formed by ozonolysis of compound A?
  A)  Only I    B)  Only II    C)  Only I and II    D)  I, II, III

 

37. Which of the following is (are) formed by ozonolysis of compound A?

 

  A)  Only I    B)  Only II    C)  I and II    D)  I, II, III

 

38. Which of the following is (are) formed by ozonolysis of the following alkyne?

 

  A)  Only I and II    B)  Only III and IV    C)  Only I and IV    D)  Only II and III

 

39. Which of the following is (are) formed by ozonolysis of the following alkyne?

 

  A)  Only I    B)  Only II    C)  I and II    D)  I, II, III

 

40. Determine the product of the following reaction.
  A)  I    B)  II    C)  III    D)  IV

 

41. Determine the product of the following reaction.
  A)  I    B)  II    C)  III    D)  IV

 

42. What is the product of the following reaction?
  A)  I    B)  II    C)  III    D)  IV

 

43. Predict the major product of the following reaction.

 

  A)  I    B)  II    C)  III    D)  IV

 

 

Answer Key

 

1. D
2. A
3. A
4. B
5. A
6. B
7. A
8. B
9. A
10. A
11. D
12. B
13. C
14. A
15. D
16. B
17. D
18. B
19. D
20. C
21. D
22. A
23. D
24. B
25. A
26. A
27. C
28. D
29. C
30. C
31. B
32. C
33. D
34. A
35. B
36. C
37. C
38. A
39. A
40. D
41. D
42. B
43. A

Chapter 24: Carbonyl Condensation Reactions

 

1. What is the general name for the reaction product formed in an aldol addition reaction?
  A) a-hydroxy carbonyl compound. C) g-hydroxy carbonyl compound.
  B) b-hydroxy carbonyl compound. D) a,b-hydroxy carbonyl compound.

 

2. In the correct order, what are the three steps in the mechanism of an Aldol reaction?
  A) Protonation, enolate formation, nucleophilic addition.
  B) Enolate formation, protonation, nucleophilic addition.
  C) Enolate formation, nucleophilic addition, protonation.
  D) Nucleophilic addition, enolate formation, protonation.

 

3. Which of the following statements about Aldol reactions with either aldehydes or ketones is true?
  A) Equilibrium favors the products with aldehydes; equilibrium favors the starting materials with ketones.
  B) Equilibrium favors the starting materials with aldehydes; equilibrium favors the products with ketones.
  C) Equilibrium favors the products with both aldehydes and ketones.
  D) Equilibrium favors the starting materials with both aldehydes and ketones.

 

4. What reaction type is an Aldol reaction?
  A) nucleophilic substitution C) electrophilic addition
  B) electrophilic substitution D) nucleophilic addition

 

5. What is the Aldol addition product formed from reaction of the following compound with itself?

 

  A)  I    B)  II    C)  III    D)  IV

 

6. What is the Aldol addition product formed from the reaction of (CH3)2CHCH2CHO with itself?
  A)  I    B)  II    C)  III    D)  IV

 

7. What is the Aldol addition product formed from the reaction of acetone, (CH3)2CO, with itself?

 

  A)  I    B)  II    C)  III    D)  IV

 

8. Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

 

  A)  I    B)  II    C)  III    D)  None of the choices

 

9. Which of the following carbonyl compounds do not undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

 

  A)  I    B)  II    C)  III    D)  IV

 

10. Why is the Aldol reaction often called an Aldol condensation?
  A) The initially formed b-hydroxy carbonyl compound loses a hydroxyl group.
  B) The initially formed b-hydroxy carbonyl compound loses an oxygen atom.
  C) The initially formed b-hydroxy carbonyl compound loses a hydrogen atom.
  D) The initially formed b-hydroxy carbonyl compound loses water.

 

11. What is the general name for the class of products formed in an Aldol condensation reaction?
  A) b,g-unsaturated carbonyl compound C) a,g-unsaturated carbonyl compound
  B) a,b-unsaturated carbonyl compound D) b-hydroxy carbonyl compound

 

12. Which is the unsaturated carbonyl compound is formed by the dehydration of the following b-hydroxy carbonyl compound?

 

  A)  I    B)  II    C)  I and II    D)  None of the choices

 

13. Which is the unsaturated carbonyl compound formed in the dehydration of the following b-hydroxy carbonyl compound?

 

  A)  I    B)  II    C)  I and II    D)  None of the choices

 

14. What aldehyde or ketone is needed to prepare the following compound by an Aldol reaction?
  A)  I    B)  II    C)  III    D)  IV

 

15. What is the name given to an Aldol reaction between two different carbonyl compounds?
  A) multiple Aldol reaction C) differential Aldol reaction
  B) crossed Aldol reaction D) versatile Aldol reaction

 

16. When is a crossed Aldol reaction said to be synthetically useful?
  A) When both carbonyl compounds have a hydrogens.
  B) When both carbonyl compounds have no a hydrogens.
  C) When one carbonyl compound has no a hydrogens.
  D) When one carbonyl compound has no b hydrogens.

 

17. In what situation can the yield of a single crossed Aldol product be increased?
  A) The electrophilic carbonyl component is relatively unhindered and is used in excess.
  B) The electrophilic carbonyl carbon component is relatively hindered and is used in limited amount.
  C) The nucleophilic carbonyl component is relatively unhindered and is used in excess.
  D) The nucleophilic carbonyl component is relatively hindered and is used in limited amount.

 

18. What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

 

  A)  I    B)  II    C)  III    D)  IV

 

19. What cyclic product is formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

 

  A)  I    B)  II    C)  III    D)  IV

 

20. What is the general name for the reaction product formed in a Claisen reaction?
  A)  b-hydroxy ester    B)  b-keto ester    C)  a-keto ester    D)  g-hydroxy ester

 

21. What reaction type is a Claisen reaction?
  A) Electrophilic addition C) Nucleophilic addition
  B) Electrophilic substitution D) Nucleophilic substitution

 

22. What type of esters can undergo Claisen reactions?
  A) All esters can undergo Claisen reactions.
  B) Only esters with two hydrogen atoms on the a carbon can undergo Claisen reactions.
  C) Only esters with three hydrogen atoms on the a carbon can undergo Claisen reactions.
  D) Only esters with two or three hydrogen atoms on the a carbon can undergo Claisen reactions.

 

23. What is the product of the following Claisen reaction?
  A)  I    B)  II    C)  III    D)  IV

 

24. What is the product of the following Claisen reaction?
  A)  I    B)  II    C)  III    D)  IV

 

25. What is the name given to the Claisen reaction between two different esters?
  A) multiple Claisen reaction C) crossed Claisen reaction
  B) differential Claisen reaction D) versatile Claisen reaction

 

26. When is a crossed Claisen reaction between two different esters synthetically useful?
  A) When only one of the esters has a hydrogen atoms.
  B) When both esters have a hydrogen atoms.
  C) When only one of the esters has b hydrogen atoms.
  D) When both esters lack a hydrogen atoms.

 

27. What is the general name of the product of a crossed Claisen reaction between a ketone and an ester?
  A) b-keto ester C) g-dicarbonyl compound
  B) a,b-dicarbonyl compound D) b-dicarbonyl compound

 

28. In the correct order, what are the three general steps in the mechanism of a Claisen reaction?
  A) Enolate formation, elimination, nucleophilic addition.
  B) Enolate formation, nucleophilic addition, elimination.
  C) Elimination, enolate formation, nucleophilic addition.
  D) Nucleophilic addition, enolate formation, elimination.

 

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29. What is an intramolecular Claisen reaction called?