Chemistry Chapter 13 1 The negative charge on the conjugate base of compound II

Chapter Thirteen

1.

What is the IUPAC name for the following compound?

CH3CHCHCHCHCH3

OH

CH3

A)

4-isopropyl-3,4-dimethyl-2-butanol

B)

2,3,4-trimethyl-4-pentanol

C)

1,1,2,3-tetramethyl-4-pentanol

D)

3,4,5-trimethyl-2-hexanol

E)

3,4,5,5-tetramethyl-2-pentanol

Ans:

D

2.

What is the IUPAC name for isobutyl alcohol?

A)

2-methyl-1-propanol

B)

2-methyl-1-butanol

C)

1-methyl-1-propanol

D)

1,1-dimethyl-1-ethanol

E)

3-methyl-1-propanol

Ans:

A

3.

What is the IUPAC name for the following compound?

CH3CH2CCH2CH3

CH2CH3

OH

A)

1,1,1-triethylmethanol

B)

1,1-diethyl-1-propanol

C)

2-ethyl-3-pentanol

D)

3-ethyl-3-pentanol

E)

t-heptanol

4.

What is the IUPAC name for t-butyl alcohol?

A)

1-butanol

B)

2-methyl-1-propanol

C)

2-methyl-2-propanol

D)

2-butanol

E)

1,1-dimethyl-1-ethanol

Ans:

C

5.

What is the IUPAC name for the following compound?

OH

A)

1-isopropyl-4-cyclopentanol

B)

3-isopropyl-1-cyclopentanol

C)

1-isopropyl-3-cyclopentanol

D)

1-isopropyl-4-hydroxycyclopentane

E)

None of these

Ans:

B

Ans:

D

6.

What is the correct structure for 1-chloro-3-ethyl-2-pentanol?

CH3CH2CCH2CH2Cl

CH2CH3

OH

CH3CHCHCH2CH2Cl

CH2CH3

OH

CH3CH2CHCHCH2Cl

CH2CH3

OH

CH3CH2CHCH2CHCl

CH2CH3

OH

III III IV

A)

I

B)

II

C)

III

D)

IV

E)

None of these

7.

What is the IUPAC name for the following compound?

Br

HO

A)

2-methyl-5-bromocyclohexanol

B)

3-bromo-2-methylcyclohexanol

C)

1-bromo-4-methylcyclohexanol

D)

4-bromo-6-methylcyclohexanol

E)

4-bromo-2-methylcyclohexanol

Ans:

E

Ans:

D

8.

What is the IUPAC name for the following compound?

CH3CH2C=CCH2CH3

CH3

CH2CH2OH

A)

3-methyl-4-ethyl-3-hexen-6-ol

B)

4-ethyl-3-methyl-3,6-hexenol

C)

3-ethyl-4-methyl-3-hexen-1-ol

D)

3-methyl-4-(2-hydroxyethyl)-3-hexene

E)

3-(2-hydroxyethyl)- 3-methyl-3-hexene

9.

What is the IUPAC name for the following compound?

OH

A)

4-penten-2-methyl-2-ol

B)

4-methyl-1-penten-2-ol

C)

2-methyl-4-penten-2-ol

D)

4-methyl-1-penten-4-ol

E)

4-hydroxy-4-methyl-1-pentene

10.

What is the IUPAC name for the following compound?

CH3

C

HO

HC

CCH2CH3

A)

(R)-3-hexyn-2-ol

B)

(S)-3-hexyn-2-ol

C)

(R)-2-hexyn-4-ol

D)

(S)-2-hexyn-4-ol

E)

(S)-2-hydroxy-3-hexyne

Ans:

C

11.

What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?

OH

Br

OH

Br Br

Br

OH

CH3CH2CH2CH2CCH(CH3)OH

Br

II

IV V

I

CH3CCH2CH2CH2CHOH

Br

CH3

III

A)

I

B)

II

C)

III

D)

IV

E)

V

Ans:

D

12.

What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?

V

IV

I

II

HO

OH

III

OH

A)

I

B)

II

C)

III

D)

IV

E)

V

13.

What is the IUPAC name for the following compound?

OH

14.

What is the IUPAC name for the following compound?

HO

15.

What is the IUPAC name for the following compound?

H Br

CH3

OH

16.

What is the IUPAC name for the following compound?

OH

17.

Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?

18.

Provide the structure for 5-chloro-2-propyl-1-heptanol.

19.

Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.

Ans:

7-cyclohexyl-2,8-dimethyl-3-decanol

20.

What is the IUPAC name for the following compound?

21.

What is the IUPAC name for the following compound?

22.

What is the IUPAC name for the following compound?

HO

23.

What is the IUPAC name for the following compound?

HO

24.

What is the IUPAC name for the following compound?

HOCH2CH2CH2OH

A)

1,2-butanediol

B)

isopropanol

C)

1-propanol

D)

1,3-propanediol

E)

1,2-ethanediol

Ans:

D

25.

What is the IUPAC name for the following compound?

OH

A)

cis-1,2-cyclopentanediol

B)

meso-1,2-cyclopentanediol

C)

(1R,2R)-1,2-cyclopentanediol

D)

(1R,2S)-1,2-cyclopentanediol

E)

(1S,2S)-1,2-cyclopentanediol

Ans:

E

26.

What is the IUPAC name for the following compound?

OH OH

27.

Provide the structure for (2R, 3S) 2-bromo-1,3-pentanediol.

28.

Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of 10. Use structural

drawings to explain your reasoning.

29.

Rank the following alcohols in decreasing order of acidity.

OH

Br

OH

F

OH

I

III III

30.

Which one of the following alcohols is most acidic?

O

OH

O

OH

III III

Ans:

I

31.

Rank the following alcohols in decreasing order of acidity. Explain your answer.

F

OH F

OH

I

III

II

FF

Ans:

II>I>III

32.

Rank the following alcohols in decreasing order of acidity.

O2N OH NC OH

OH

III III

33.

Predict the product(s) for the following reaction.

OH Na

34.

Predict the product for the following reaction.

OH 1. NaH

2. CH3CH2Br

35.

Provide the reagents necessary to carry out the following conversion.

CH3CH2CH2CHCH3

Br

CH3CH2CH2CH2CH2OH

36.

Predict the product(s) for the following reaction.

1. BH3

2. H2O2/NaOH/H2O

OH OH

OH

CH2OH

III III IV

+ enantiomer + enantiomer

A)

I

B)

II

C)

III

D)

IV

E)

None of these

Ans:

B

37.

Predict the product for the following reaction.

1. Hg(OAc)2, H2O

2. NaBH4

OH

OH CH2OH

III III IV

A)

I

B)

II

C)

III

D)

IV

E)

None of these

38.

Provide the reagents necessary to carry out the following conversion.

(E)-3-methyl-3-hexene 3-methyl-3-hexanol

39.

Predict the major product for the following reaction.

H3O+

Ans:

C

40.

Predict the product for the following reaction.

1. Hg(OAc)2, H2O

2. NaBD4

OH

OH D

OH

D OH

III III IV V

A)

I

B)

II

C)

III

D)

IV

E)

V

Ans:

C

41.

Provide the reagents necessary to carry out the following conversion.

Br OH

42.

Provide the reagents necessary to carry out the following conversion.

OH

Cl

A)

NaOH/H2O

B)

1. NaOCH3, 2. H3O+

C)

1. (CH3)3COK, 2. BH3, 3. H2O2/NaOH/H2O

D)

1. (CH3)3COK, 2. H3O+

E)

B & D

43.

What is the oxidation state of the carbon atoms I and II in the following reaction?

I

O

H

II

A)

I. +1, II. +2

B)

I. +2, II. +2

C)

I. +1, II. +3

D)

I. +3, II. +2

E)

I. +2, II. +1

Ans:

E

44.

What is the oxidation state of the carbon atoms I and II in the following reaction?

CH3CH

O

CH3COH

O

III

A)

I. +1, II. +2

B)

I. +2, II. +2

C)

I. +1, II. +3

D)

I. +3, II. +2

E)

I. +2, II. +1

Ans:

D

45.

For the following conversion, identify if the starting material has been oxidized, reduced

or neither. Explain your answer.

OH O

46.

For the following conversion, identify if the starting material has been oxidized, reduced

or neither.

Cl

47.

For the following conversion, identify if the starting material has been oxidized, reduced

or neither. Explain your answer.

OH O

48.

For the following conversion, identify if the starting material has been oxidized, reduced

or neither.

O

H

A)

reduced

B)

oxidized

C)

neither

D)

A & B

49.

Predict the product for the following reaction.

CH3CCH2CH2CH3

O

NaBH4/CH3OH

50.

Predict the product for the following reaction.

H

O

NaBH4/CH3OH

OH OH

OH

O

OH

III III IV

A)

I

B)

II

C)

III

D)

IV

Ans:

B

51.

Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4

followed by water?

O

H

O

H

OO

O

III III

IV V

A)

I

B)

II

C)

III

D)

IV

E)

V

A

52.

Provide the reagents necessary to carry out the following conversion.

HC CCH2CH2CH3CH3CHCH2CH2CH3

OH

53.

Predict the product for the following reaction.

H

O

H2.Pd

OH OH

OH

O

OH

III III IV

A)

I

B)

II

C)

III

D)

IV

54.

Predict the product for the following reaction.

COCH3

O

NaBH4 / H2O

Ans:

C