The structure of D − aldopentoses that will give optically active aldaric acids on oxidation with HNO 3 . Interpretation: The structure of D − aldopentoses that will give optically active aldaric acids on oxidation with HNO 3 are to be stated. Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

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Answer 1

Question

Chapter 23, Problem 23.59SP

(a)

Interpretation Introduction

To determine: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(b)

Interpretation Introduction

To determine: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(c)

Interpretation Introduction

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(d)

Interpretation Introduction

To determine: If the given information contradicts the principle that optically inactive reagents cannot form optically active products.

Interpretation: The validation of the statement that optically inactive reagents cannot form optically active products for the given information is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(e)

Interpretation Introduction

To determine: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded product using nitric acid.

Interpretation: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded productusing nitric acid. is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

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Draw the products formed when β-D-galactose is treated with each reagent. a. Ag2O + CH3I b. NaH + C6H5CH2Cl c. The product in (b), then H3O+ d. Ac2O + pyridine e. C6H5COCl + pyridine f. The product in (c), then C6H5COCl + pyridine

a) The D-aldopentose A, C5H1005, reacts with HNO3 to yield an optically active aldaric acid B. Kiliani-Fischer chain extension of A produces a pair of D-aldohexoses C and D. C is converted by HNO3 to an optically active aldaric acid, but D is converted by HNO3 to an optically inactive aldaric acid. Write acyclic Fischer projections for A, B, C, D. b) Disaccharide E is a reducing sugar. It is hydrolyzed by an α-glycosidase enzyme, which means it contains an α- glycoside link. Treatment of E with Ag2O and excess Mel gives an octamethyl derivative F. Hydrolysis of F in dilute aqueous acid gives the pair of molecules shown below. Write the structures of E and F. (If the stereochemistry at a particular carbon is not determined by the above data, indicate this with a wavy line as shown below.) HO OMe OMe MeO MeO MOH OMe mOH OMe OMe

a) The D-aldopentose A, C5H1005, reacts with HNO3 to yield an optically active aldaric acid B. Kiliani-Fischer chain extension of A produces a pair of D-aldohexoses C and D. C is converted by HNO3 to an optically active aldaric acid, but D is converted by HNO3 to an optically inactive aldaric acid. Write acyclic Fischer projections for A, B, C, D.

Answer 2

Question

Chapter 23, Problem 23.59SP

(a)

Interpretation Introduction

To determine: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(b)

Interpretation Introduction

To determine: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(c)

Interpretation Introduction

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(d)

Interpretation Introduction

To determine: If the given information contradicts the principle that optically inactive reagents cannot form optically active products.

Interpretation: The validation of the statement that optically inactive reagents cannot form optically active products for the given information is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(e)

Interpretation Introduction

To determine: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded product using nitric acid.

Interpretation: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded productusing nitric acid. is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

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Answer 3

Question

Chapter 23, Problem 23.59SP

(a)

Interpretation Introduction

To determine: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(b)

Interpretation Introduction

To determine: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(c)

Interpretation Introduction

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(d)

Interpretation Introduction

To determine: If the given information contradicts the principle that optically inactive reagents cannot form optically active products.

Interpretation: The validation of the statement that optically inactive reagents cannot form optically active products for the given information is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(e)

Interpretation Introduction

To determine: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded product using nitric acid.

Interpretation: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded productusing nitric acid. is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

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Answer 4

Question

Chapter 23, Problem 23.59SP

(a)

Interpretation Introduction

To determine: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(b)

Interpretation Introduction

To determine: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(c)

Interpretation Introduction

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(d)

Interpretation Introduction

To determine: If the given information contradicts the principle that optically inactive reagents cannot form optically active products.

Interpretation: The validation of the statement that optically inactive reagents cannot form optically active products for the given information is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(e)

Interpretation Introduction

To determine: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded product using nitric acid.

Interpretation: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded productusing nitric acid. is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

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Answer 5

Chapter 23, Problem 23.59SP

(a)

Interpretation Introduction

To determine: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(b)

Interpretation Introduction

To determine: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(c)

Interpretation Introduction

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(d)

Interpretation Introduction

To determine: If the given information contradicts the principle that optically inactive reagents cannot form optically active products.

Interpretation: The validation of the statement that optically inactive reagents cannot form optically active products for the given information is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

(e)

Interpretation Introduction

To determine: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded product using nitric acid.

Interpretation: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded productusing nitric acid. is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 6

Chapter 23, Problem 23.59SP

(a)

Interpretation Introduction

To determine: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 7

Chapter 23, Problem 23.59SP

(a)

Interpretation Introduction

To determine: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldopentoses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 8

(b)

Interpretation Introduction

To determine: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 9

(b)

Interpretation Introduction

To determine: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3.

Interpretation: The structure of D−aldotetroses that will give optically active aldaric acids on oxidation with HNO3 are to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 10

(c)

Interpretation Introduction

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 11

(c)

Interpretation Introduction

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 12

(d)

Interpretation Introduction

To determine: If the given information contradicts the principle that optically inactive reagents cannot form optically active products.

Interpretation: The validation of the statement that optically inactive reagents cannot form optically active products for the given information is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 13

(d)

Interpretation Introduction

To determine: If the given information contradicts the principle that optically inactive reagents cannot form optically active products.

Interpretation: The validation of the statement that optically inactive reagents cannot form optically active products for the given information is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 14

(e)

Interpretation Introduction

To determine: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded product using nitric acid.

Interpretation: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded productusing nitric acid. is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 15

(e)

Interpretation Introduction

To determine: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded product using nitric acid.

Interpretation: The aldotetrose product obtained after the further degradation of aldopentose and the product formed after the oxidation of the degraded productusing nitric acid. is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Answer 16

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Answer 17

Expert Solution & Answer

Answer 18

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Answer 19

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

Solution Summary: The author explains the structure of D- aldopentoses that will give optically active aldaric acids on oxidation.

Concept explainers

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

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Chapter 23 Solutions

Solution Summary: The author explains the structure of D- aldopentoses that will give optically active aldaric acids on oxidation.

Concept explainers

To determine: The structure of given aldohexose X. Interpretation: The structure of given aldohexose X is to be stated. Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.

Want to see the full answer?

Chapter 23 Solutions

To determine: The structure of given aldohexose X.

Interpretation: The structure of given aldohexose X is to be stated.

Concept introduction: The species that are asymmetric in nature have a tendency to rotate plane of polarized light and is thus optically active in nature.