The structure of methyl β -D-glucopyranoside is to be drawn. Concept introduction: Methyl β -D-glucopyranoside has molecular formula C 7 H 14 O 6 . A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

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Answer 1

Question

Chapter 23, Problem 23.53SP

(a)

Interpretation Introduction

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

(b)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose is to be drawn.

Concept introduction

The molecular formula of 2,3,4,6 tetra-O-methyl-D-mannopyranose is C10H20O6. Four OCH3 groups are present in structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose.

Pyranose is a six membered cyclic hemiacetal form of sugar.

(c)

Interpretation Introduction

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

(d)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

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Identify the missing starting materials/ reagents/ products in the following reactions. Show the stereochemistry clearly in the structures, if any. If there is a major product, draw the structures of the major product with stereochemistry clearly indicated where applicable. Show only the diastereomers (you do not have to draw the pairs of enantiomers). If you believe that multiple products are formed in approximately equal amounts (hence neither is the major product), draw the structures of the products, and show the detailed mechanism of these reactions to justify the formation of the multiple products. If you believe no product is formed, explain why briefly. (6 mark for each, except f and g, which are 10 mark each)

3. What starting material would you use to synthesize 3-hydroxypentanoic acid using a NaBH4 reduction?

1. Give stereochemical (Fischer projection) formulas for all (but no extras) the stereoisomers that could theoretically form during the reduction of a. the carbonyl group of 2-methyl-3--pentanone b. both carbonyl groups of 2,4-pentanedione (careful!) 2. Predict the products of the reduction of O=CCH2CH2CH2C=O with a. LiAlH4 b. NaBH4 CH3 OH

Answer 2

Question

Chapter 23, Problem 23.53SP

(a)

Interpretation Introduction

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

(b)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose is to be drawn.

Concept introduction

The molecular formula of 2,3,4,6 tetra-O-methyl-D-mannopyranose is C10H20O6. Four OCH3 groups are present in structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose.

Pyranose is a six membered cyclic hemiacetal form of sugar.

(c)

Interpretation Introduction

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

(d)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

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Answer 3

Question

Chapter 23, Problem 23.53SP

(a)

Interpretation Introduction

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

(b)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose is to be drawn.

Concept introduction

The molecular formula of 2,3,4,6 tetra-O-methyl-D-mannopyranose is C10H20O6. Four OCH3 groups are present in structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose.

Pyranose is a six membered cyclic hemiacetal form of sugar.

(c)

Interpretation Introduction

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

(d)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

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Answer 4

Question

Chapter 23, Problem 23.53SP

(a)

Interpretation Introduction

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

(b)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose is to be drawn.

Concept introduction

The molecular formula of 2,3,4,6 tetra-O-methyl-D-mannopyranose is C10H20O6. Four OCH3 groups are present in structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose.

Pyranose is a six membered cyclic hemiacetal form of sugar.

(c)

Interpretation Introduction

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

(d)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

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Answer 5

Chapter 23, Problem 23.53SP

(a)

Interpretation Introduction

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

(b)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose is to be drawn.

Concept introduction

The molecular formula of 2,3,4,6 tetra-O-methyl-D-mannopyranose is C10H20O6. Four OCH3 groups are present in structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose.

Pyranose is a six membered cyclic hemiacetal form of sugar.

(c)

Interpretation Introduction

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

(d)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Answer 6

Chapter 23, Problem 23.53SP

(a)

Interpretation Introduction

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Answer 7

Chapter 23, Problem 23.53SP

(a)

Interpretation Introduction

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose is to be drawn.

Concept introduction

The molecular formula of 2,3,4,6 tetra-O-methyl-D-mannopyranose is C10H20O6. Four OCH3 groups are present in structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose.

Pyranose is a six membered cyclic hemiacetal form of sugar.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose is to be drawn.

Concept introduction

The molecular formula of 2,3,4,6 tetra-O-methyl-D-mannopyranose is C10H20O6. Four OCH3 groups are present in structure of 2,3,4,6 tetra-O-methyl-D-mannopyranose.

Pyranose is a six membered cyclic hemiacetal form of sugar.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

Answer 12

(d)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Answer 13

(d)

Interpretation Introduction

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Answer 14

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Answer 15

Expert Solution & Answer

Answer 16

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Answer 17

Ch. 23.2 - Prob. 23.1P Ch. 23.3A - Prob. 23.2P Ch. 23.3A - Prob. 23.3P Ch. 23.3B - Draw and name the enantiomers of the sugars shown...Ch. 23.3B - Prob. 23.5P Ch. 23.3C - Prob. 23.6P Ch. 23.4 - Draw the Haworth projection for the cyclic...Ch. 23.4 - Prob. 23.8P Ch. 23.4 - Prob. 23.9P Ch. 23.4 - Prob. 23.10P

The structure of methyl β -D-glucopyranoside is to be drawn. Concept introduction: Methyl β -D-glucopyranoside has molecular formula C 7 H 14 O 6 . A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Solution Summary: The author explains the structure of methyl beta -D-glucopyranoside and tetra- O -methyl-d-mannopyranose.

Concept explainers

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

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Chapter 23 Solutions

The structure of methyl β -D-glucopyranoside is to be drawn. Concept introduction: Methyl β -D-glucopyranoside has molecular formula C 7 H 14 O 6 . A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Solution Summary: The author explains the structure of methyl beta -D-glucopyranoside and tetra- O -methyl-d-mannopyranose.

Concept explainers

Interpretation: The structure of methyl β-D-glucopyranoside is to be drawn. Concept introduction: Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Interpretation: The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn. Concept introduction: Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

Interpretation: The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn. Concept introduction: Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

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Chapter 23 Solutions

Interpretation:

The structure of methyl β-D-glucopyranoside is to be drawn.

Concept introduction:

Methyl β-D-glucopyranoside has molecular formula C7H14O6. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.

Interpretation:

The structure of 1,3,6 tri-O-methyl-D-fructofuranose is to be drawn.

Concept introduction:

Furanose is a five membered cyclic hemiacetal form of a sugar. It consists of four carbon atoms and one oxygen atoms. Furanose rings have alpha and beta configuration.

Interpretation:

The structure of 2,3,4,6 tetra-O-methyl-β-D-glactopyranoside is to be drawn.

Concept introduction:

Pyranoside is a six membered glycoside. A cyclic acetal form of sugar is known as glycoside. It is a non reducing sugar. Glycosides are generally furanosides or pyranosides.