(a) Interpretation: The glycosidic linkage and acetal carbon in the lactose are to be identified. Concept introduction: An acetal is characterized by a C atom bonded to two alkyl (or H) groups and two alkoxy (RO–) groups. The compound in which the OH from a sugar molecule has been replaced by OR is called glycoside. The C-O-C bond that connects the sugars is called glycosidic linkage.

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Answer 1

Question

Chapter 9, Problem 9.77P

Interpretation Introduction

(a)

Interpretation:

The glycosidic linkage and acetal carbon in the lactose are to be identified.

Concept introduction:

An acetal is characterized by a C atom bonded to two alkyl (or H) groups and two alkoxy (RO–) groups. The compound in which the OH from a sugar molecule has been replaced by OR is called glycoside. The C-O-C bond that connects the sugars is called glycosidic linkage.

Interpretation Introduction

(b)

Interpretation:

The type of glycosidic linkage that lactose has is to be determined.

Concept introduction:

If the alkoxy (RO-) group on the acetal carbon is in axial position, it is designated as α, and if it is in equatorial position, it is designated as β. If the ring on the other side of glycosidic linkage is bonded to C4, it is notified as 1, 4’, where the prime (’) indicates that C4 and C1 are on different sugar units.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism and the products of the acid catalyzed hydrolysis of lactose are to be drawn.

Concept introduction:

The acid catalyzed hydrolysis of lactose gives two monosaccharides, which are linked by glycoside linkage. In Step 1, protonation of electron rich O atom takes place. The bond of acetal carbon and electron poor O of the glycosidic linkage breaks in heterolysis step. In Step 3, the newly formed carbocation is attacked by water as a nucleophile. This can take place on either side of the plane of the carbocation C. Finally, in Step 4, deprotonation removes the positive charge from O and forms D-Galactose.

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(a 4 shows scanning electron microscope (SEM) images of extruded actions of packing bed for two capillary columns of different diameters, al 750 (bottom image) and b) 30-μm-i.d. Both columns are packed with the same stationary phase, spherical particles with 1-um diameter. A) When the columns were prepared, the figure shows that the column with the larger diameter has more packing irregularities. Explain this observation. B) Predict what affect this should have on band broadening and discuss your prediction using the van Deemter terms. C) Does this figure support your explanations in application question 33? Explain why or why not and make any changes in your answers in light of this figure. Figure 4 SEM images of sections of packed columns for a) 750 and b) 30-um-i.d. capillary columns.³

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Answer 2

Question

Chapter 9, Problem 9.77P

Interpretation Introduction

(a)

Interpretation:

The glycosidic linkage and acetal carbon in the lactose are to be identified.

Concept introduction:

An acetal is characterized by a C atom bonded to two alkyl (or H) groups and two alkoxy (RO–) groups. The compound in which the OH from a sugar molecule has been replaced by OR is called glycoside. The C-O-C bond that connects the sugars is called glycosidic linkage.

Interpretation Introduction

(b)

Interpretation:

The type of glycosidic linkage that lactose has is to be determined.

Concept introduction:

If the alkoxy (RO-) group on the acetal carbon is in axial position, it is designated as α, and if it is in equatorial position, it is designated as β. If the ring on the other side of glycosidic linkage is bonded to C4, it is notified as 1, 4’, where the prime (’) indicates that C4 and C1 are on different sugar units.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism and the products of the acid catalyzed hydrolysis of lactose are to be drawn.

Concept introduction:

The acid catalyzed hydrolysis of lactose gives two monosaccharides, which are linked by glycoside linkage. In Step 1, protonation of electron rich O atom takes place. The bond of acetal carbon and electron poor O of the glycosidic linkage breaks in heterolysis step. In Step 3, the newly formed carbocation is attacked by water as a nucleophile. This can take place on either side of the plane of the carbocation C. Finally, in Step 4, deprotonation removes the positive charge from O and forms D-Galactose.

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Answer 3

Question

Chapter 9, Problem 9.77P

Interpretation Introduction

(a)

Interpretation:

The glycosidic linkage and acetal carbon in the lactose are to be identified.

Concept introduction:

An acetal is characterized by a C atom bonded to two alkyl (or H) groups and two alkoxy (RO–) groups. The compound in which the OH from a sugar molecule has been replaced by OR is called glycoside. The C-O-C bond that connects the sugars is called glycosidic linkage.

Interpretation Introduction

(b)

Interpretation:

The type of glycosidic linkage that lactose has is to be determined.

Concept introduction:

If the alkoxy (RO-) group on the acetal carbon is in axial position, it is designated as α, and if it is in equatorial position, it is designated as β. If the ring on the other side of glycosidic linkage is bonded to C4, it is notified as 1, 4’, where the prime (’) indicates that C4 and C1 are on different sugar units.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism and the products of the acid catalyzed hydrolysis of lactose are to be drawn.

Concept introduction:

The acid catalyzed hydrolysis of lactose gives two monosaccharides, which are linked by glycoside linkage. In Step 1, protonation of electron rich O atom takes place. The bond of acetal carbon and electron poor O of the glycosidic linkage breaks in heterolysis step. In Step 3, the newly formed carbocation is attacked by water as a nucleophile. This can take place on either side of the plane of the carbocation C. Finally, in Step 4, deprotonation removes the positive charge from O and forms D-Galactose.

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Answer 4

Question

Chapter 9, Problem 9.77P

Interpretation Introduction

(a)

Interpretation:

The glycosidic linkage and acetal carbon in the lactose are to be identified.

Concept introduction:

An acetal is characterized by a C atom bonded to two alkyl (or H) groups and two alkoxy (RO–) groups. The compound in which the OH from a sugar molecule has been replaced by OR is called glycoside. The C-O-C bond that connects the sugars is called glycosidic linkage.

Interpretation Introduction

(b)

Interpretation:

The type of glycosidic linkage that lactose has is to be determined.

Concept introduction:

If the alkoxy (RO-) group on the acetal carbon is in axial position, it is designated as α, and if it is in equatorial position, it is designated as β. If the ring on the other side of glycosidic linkage is bonded to C4, it is notified as 1, 4’, where the prime (’) indicates that C4 and C1 are on different sugar units.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism and the products of the acid catalyzed hydrolysis of lactose are to be drawn.

Concept introduction:

The acid catalyzed hydrolysis of lactose gives two monosaccharides, which are linked by glycoside linkage. In Step 1, protonation of electron rich O atom takes place. The bond of acetal carbon and electron poor O of the glycosidic linkage breaks in heterolysis step. In Step 3, the newly formed carbocation is attacked by water as a nucleophile. This can take place on either side of the plane of the carbocation C. Finally, in Step 4, deprotonation removes the positive charge from O and forms D-Galactose.

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Answer 5

Chapter 9, Problem 9.77P

Interpretation Introduction

(a)

Interpretation:

The glycosidic linkage and acetal carbon in the lactose are to be identified.

Concept introduction:

An acetal is characterized by a C atom bonded to two alkyl (or H) groups and two alkoxy (RO–) groups. The compound in which the OH from a sugar molecule has been replaced by OR is called glycoside. The C-O-C bond that connects the sugars is called glycosidic linkage.

Interpretation Introduction

(b)

Interpretation:

The type of glycosidic linkage that lactose has is to be determined.

Concept introduction:

If the alkoxy (RO-) group on the acetal carbon is in axial position, it is designated as α, and if it is in equatorial position, it is designated as β. If the ring on the other side of glycosidic linkage is bonded to C4, it is notified as 1, 4’, where the prime (’) indicates that C4 and C1 are on different sugar units.

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism and the products of the acid catalyzed hydrolysis of lactose are to be drawn.

Concept introduction:

The acid catalyzed hydrolysis of lactose gives two monosaccharides, which are linked by glycoside linkage. In Step 1, protonation of electron rich O atom takes place. The bond of acetal carbon and electron poor O of the glycosidic linkage breaks in heterolysis step. In Step 3, the newly formed carbocation is attacked by water as a nucleophile. This can take place on either side of the plane of the carbocation C. Finally, in Step 4, deprotonation removes the positive charge from O and forms D-Galactose.

Answer 6

Chapter 9, Problem 9.77P

Interpretation Introduction

(a)

Interpretation:

The glycosidic linkage and acetal carbon in the lactose are to be identified.

Concept introduction:

An acetal is characterized by a C atom bonded to two alkyl (or H) groups and two alkoxy (RO–) groups. The compound in which the OH from a sugar molecule has been replaced by OR is called glycoside. The C-O-C bond that connects the sugars is called glycosidic linkage.

Answer 7

Chapter 9, Problem 9.77P

Interpretation Introduction

(a)

Interpretation:

The glycosidic linkage and acetal carbon in the lactose are to be identified.

Concept introduction:

An acetal is characterized by a C atom bonded to two alkyl (or H) groups and two alkoxy (RO–) groups. The compound in which the OH from a sugar molecule has been replaced by OR is called glycoside. The C-O-C bond that connects the sugars is called glycosidic linkage.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The type of glycosidic linkage that lactose has is to be determined.

Concept introduction:

If the alkoxy (RO-) group on the acetal carbon is in axial position, it is designated as α, and if it is in equatorial position, it is designated as β. If the ring on the other side of glycosidic linkage is bonded to C4, it is notified as 1, 4’, where the prime (’) indicates that C4 and C1 are on different sugar units.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The type of glycosidic linkage that lactose has is to be determined.

Concept introduction:

If the alkoxy (RO-) group on the acetal carbon is in axial position, it is designated as α, and if it is in equatorial position, it is designated as β. If the ring on the other side of glycosidic linkage is bonded to C4, it is notified as 1, 4’, where the prime (’) indicates that C4 and C1 are on different sugar units.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism and the products of the acid catalyzed hydrolysis of lactose are to be drawn.

Concept introduction:

The acid catalyzed hydrolysis of lactose gives two monosaccharides, which are linked by glycoside linkage. In Step 1, protonation of electron rich O atom takes place. The bond of acetal carbon and electron poor O of the glycosidic linkage breaks in heterolysis step. In Step 3, the newly formed carbocation is attacked by water as a nucleophile. This can take place on either side of the plane of the carbocation C. Finally, in Step 4, deprotonation removes the positive charge from O and forms D-Galactose.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The complete, detailed mechanism and the products of the acid catalyzed hydrolysis of lactose are to be drawn.

Concept introduction:

The acid catalyzed hydrolysis of lactose gives two monosaccharides, which are linked by glycoside linkage. In Step 1, protonation of electron rich O atom takes place. The bond of acetal carbon and electron poor O of the glycosidic linkage breaks in heterolysis step. In Step 3, the newly formed carbocation is attacked by water as a nucleophile. This can take place on either side of the plane of the carbocation C. Finally, in Step 4, deprotonation removes the positive charge from O and forms D-Galactose.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 9 - Prob. 9.1P Ch. 9 - Prob. 9.2P Ch. 9 - Prob. 9.3P Ch. 9 - Prob. 9.4P Ch. 9 - Prob. 9.5P Ch. 9 - Prob. 9.6P Ch. 9 - Prob. 9.7P Ch. 9 - Prob. 9.8P Ch. 9 - Prob. 9.9P Ch. 9 - Prob. 9.10P

Solution Summary: The author explains the glycosidic linkage and acetal carbon in the lactose.

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