Chemistry Chapter 24 2 When D-glucose is treated with aqueous NaOH it undergoes

47.

Predict the product(s) for the following reaction.

CH3OH

HCl

–D–galactopyranose

48.

Predict the product(s) for the following reaction.

O

OH

HO

OH

OCH3

OH

H3O+

O

OH

HO

OH

O

OH

HO

OH

HO

OH

C

OHH

HHO

OHH

CH2OH

O H

III III

IV

A)



B)

  

C)

  V

D)

IV

E)

I, II & IV

Ans:

E

49.

D-glucose & D-galactose are ______ epimers of each other.

A)

C-1

B)

C-2

C)

C-3

D)

C-4

E)

C-5

50.

D-ribulose & D-xylulose are ______epimers of each other.

A)

C-1

B)

C-2

C)

C-3

D)

C-4

E)

C-5

Ans:

C

51.

When D-glucose is treated with aqueous NaOH it undergoes_______.

A)

mutarotation

B)

oxidation

C)

glycoside formation

D)

epimerization

E)

none of these

Ans:

D

Ans:

D

52.

Predict the product(s) for the following reaction.

NaBH4

H2O

D-galactose

C

OHH

HHO

OHH

C

O OH

OHO

IV

CH3

OHH

HHO

OHH

CH2OH

I

C

OHH

HHO

OHH

CH2OH

O OH

II

CH2OH

OHH

HHO

OHH

CH2OH

III

A)

I

B)

II

C)

III

D)

IV

E)

II & IV

53.

Predict the product(s) for the following reaction.

NaBH4

H2O

D-fructose

CH2OH

HH

HHO

OHH

CH2OH

IV

CH2OH

OHH

HHO

OHH

CH2OH

I

CH2OH

OHH

HHO

OHH

CH2OH

II

CH2OH

HHO

OHH

CH2OH

III

CH2OH

OHH

CH2OH

V

A)

I

B)

II

C)

I & III

D)

IV

E)

I &V

Ans:

C

Ans:

C

54.

Which of the following D-aldoses will produce an optically inactive product when

treated with NaBH4/H2O?

C

OHH

HHO

OHH

CH2OH

O H

IV

C

OHH

HHO

OHH

CH2OH

I

C

HHO

OHH

CH2OH

O H

II

C

OHH

CH2OH

III

O H O H

A)

I

B)

II

C)

III

D)

IV

E)

none of these

Ans:

C

55.

When D-threose is treated with NaBH4/H2O, it forms

A)

a racemic mixture of alditols

B)

a meso alditol

C)

an optically active alditol

D)

an optically active aldonic acid

E)

none of these

Ans:

C

56.

Which of the following compound(s) would give a positive Tollen’s test?

O

OH

HO

OH

O

OCH3

HO

OH

HO

OH

III

O

OCH3

H3CO

OCH3

H3CO

OCH3

O

OH

OCH3

OH

IV

III

OH

A)

I

B)

II

C)

III

D)

IV

E)

I & II

57.

Which one of the following compounds is a non reducing sugar?

O

OH

HO

OH

O

OCH3

HO

OH

HO

OH

III

O

OH

OCH3

OH

IV

III

CH2OH

OH

CH2OH

OH

O

A)

I

B)

II

C)

III

D)

IV

E)

none of these

Ans:

C

Ans:

E

58.

Which one of the following compounds would give a positive test with Benedict’s

solution?

O

OCH3

H3CO

OCH3

O

OCH3

HO

OH

HO

OH

III

O

OH

OCH3

OH

IV

III

CH2OH

OCH3

CH2OH

OH

O

A)

I

B)

II

C)

III

D)

IV

E)

none of these

Ans:

B

59.

Predict the product(s) for the following reaction.

D–mannose Br2/H2O

C

HHO

OHH

C

O OH

OHO

C

HHO

OHH

C

O H

OHO

C

HHO

OHH

CH2OH

O OH

C

HHO

OHH

C

O H

HO

III III IV V

C

OHH

HHO

OHH

CH2OH

O OH

A)

I

B)

II

C)

III

D)

IV

E)

V

60.

Predict the product(s) for the following reaction.

D–xylose Br2/H2O

Ans:

D

61.

Predict the product(s) for the following reaction.

D-galactose HNO3

C

OHH

HHO

OHH

C

O OH

OHO

C

HHO

OHH

C

O OH

OHO

C

OHH

HHO

OHH

CH2OH

O OH

C

HHO

OHH

C

O OH

OHO

III III IV V

C

OHH

HHO

OHH

CH2OH

O OH

A)

I

B)

II

C)

III

D)

IV

E)

V

62.

When D-ribose is treated with nitric acid, it forms

A)

a racemic mixture of aldonic acids

B)

a meso aldaric acid

C)

an optically active aldaric acid

D)

an optically active aldonic acid

E)

a meso aldonic acid

Ans:

B

Ans:

A

63.

Which of the following compound(s) would produce an optically active aldaric acid?

C

HHO

OHH

HHO

CH2OH

O H

C

OHH

HHO

OHH

CH2OH

O H

C

OHH

HHO

CH2OH

O H

C

HHO

CH2OH

O H

III III IV V

C

OHH

CH2OH

O H

A)

I

B)

II

C)

III

D)

IV

E)

V

64.

Predict the product(s) for the following reaction.

D-fructose HNO3

Ans:

D

65.

Provide the reagents necessary to carry out the following conversion.

C

HHO

OHH

HHO

CH2OH

O H

C

HHO

OHH

HHO

CH2OH

O OH

A)

Br2/H2O

B)

NaOH/H2O

C)

HNO3

D)

Ag+/NH3/H2O

E)

A & D

66.

Which of the following compound(s) would produce D-glucose and D-mannose when

treated with HCN followed by H2/Pd/BaSO4/H2O?

C

HHO

OHH

HHO

CH2OH

O H

C

OHH

CH2OH

O H

C

OHH

HHO

CH2OH

O H

C

HHO

OHH

CH2OH

O H

C

HHO

OHH

CH2OH

O H

III III IV V

A)

I

B)

II

C)

III

D)

IV

E)

V

Ans:

E

Ans:

E

67.

Predict the product(s) for the following Kiliani-Fischer synthesis.

D-ribose 1. HCN

2. H2/Pd/BaSO4/H2O

C

OHH

CH2OH

O H

C

HHO

OHH

CH2OH

O H

C

OHH

HHO

OHH

CH2OH

O H

C

HHO

OHH

CH2OH

O H

III III IV V

C

OHH

HHO

OHH

CH2OH

O H

A)

I & V

B)

II & IV

C)

I & III

D)

III & IV

E)

II & V

68.

Which aldose would produce D-ribose and D-arabinose when subjected to Kiliani-

Fischer synthesis?

A)

D-threose

B)

D-xylose

C)

D-erythrose

D)

D-allose

E)

D-Lyxose

Ans:

C

Ans:

A

69.

Predict the product(s) for the following Kiliani-Fischer synthesis.

D-lyxose

1. HCN

2. H2/Pd/BaSO4/H2O

C

HHO

OHH

CH2OH

O H

A)

D-ribose & D-arabinose

B)

D-glucose & D-galactose

C)

D-altose & D-mannose

D)

D-galactose & D-talose

E)

D-gulose & D-iodose

70.

Provide the reagents necessary to carry out the following Kiliani-Fischer synthesis.

C

HHO

OHH

O H

C

OHH

HHO

O H

C

HHO

O H

H OH

CH2OH

H OH

CH2OH

+

A)

1. HCN, 2. H2/Pd/BaSO4/H2O

B)

1. NaBH4/H2O, 2. CH3OH/HCl

C)

excess CH3I/Ag2O

D)

1. NH2OH, 2. acetic anhydride, 3. NaOCH3

E)

1. Br2/H2O, 2. NaBH4/H2O

Ans:

A

Ans:

D

71.

Which of the following compound(s) would produce D-glucose and D-mannose when

subjected to Kiliani-Fischer synthesis?

C

HHO

OHH

HHO

CH2OH

O H

C

OHH

CH2OH

O H

C

OHH

HHO

CH2OH

O H

C

HHO

OHH

CH2OH

O H

C

HHO

OHH

CH2OH

O H

III III IV V

A)

I

B)

II

C)

III

D)

IV

E)

V

72.

Predict the product(s) for the following Wohl degradation.

NH2OH O

O O

NaOCH3

D-galactose

C

HHO

OHH

HHO

CH2OH

O H

C

OHH

CH2OH

O H

C

OHH

HHO

CH2OH

O H

C

HHO

OHH

CH2OH

O H

C

HHO

OHH

CH2OH

O H

III III IV V

A)

I

B)

II

C)

III

D)

IV

E)

V

Ans:

D

Ans:

E

73.

Predict the product(s) for the following Wohl degradation.

NH2OH O

O O

NaOCH3

D-gulose

C

HHO

OHH

HHO

CH2OH

O H

C

OHH

CH2OH

O H

C

OHH

HHO

OHH

CH2OH

O H

C

HHO

OHH

CH2OH

O H

C

HHO

OHH

CH2OH

O H

III III IV V

A)

I

B)

II

C)

III

D)

IV

E)

V

Ans:

C

74.

Predict the product(s) for the following reaction.

NH2OH O

O O

NaOCH3

D-xylose