Concept explainers
a.
To determine:
Whether the Fisher projection of pairs of carbohydrates (a.) are structural isomers, enantiomers, diastereomers, or epimers of each other. Also identify each as D- or L-isomers.
Introduction:
When two isomeric molecules have similar molecular formula and same sequence of bonded atoms but differ in spatial orientations of their atoms are known as stereoisomers. The number of stereoisomer of a compound increases with the increase in chiral centre of a molecule.
When a carbon atom is attached to four different atoms it is known as a chiral center. A compound is having only one chiral center can occur in two different arrangements called enantiomers. The molecules that are the mirror images of each are enantiomers. Diastereomers are those stereoisomers who differ in orientation of more than one chiral center due to which the isomers are not the mirror images of each other. Epimers are those diastereomers which differ at only one chiral center arrangement.
There are two forms of enantiomers: L and D- forms. For example in glyceraldehyde molecule, L-form of enantiomers of glyceraldehyde has the -OH groups at the chiral center present far from carbonyl on the left side of the molecule. In D-form, glyceraldehyde has the -OH groups at the chiral center present far from carbonyl on the right side of the molecule.
b.
To determine:
Whether the Fisher projection of pairs of carbohydrates (b.) are structural isomers, enantiomers, diastereomers, or epimers of each other. Also identify each as D- or L-isomers.
Introduction:
When two isomeric molecules have similar molecular formula and same sequence of bonded atoms but differ in spatial orientations of their atoms are known as stereoisomers. The number of stereoisomer of a compound increases with the increase in chiral centre of a molecule.
When a carbon atom is attached to four different atoms it is known as a chiral center. A compound having only one chiral center can occur in two different arrangements called enantiomers. The molecules that are the mirror images of each are enantiomers. Diastereomers are those stereoisomers who differ in orientation of more than one chiral center due to which the isomers are not the mirror images of each other. Epimers are those diastereomers which differ at only one chiral center arrangement.
There are two forms of enantiomers: L and D- forms. For example in glyceraldehyde molecule, L-form of enantiomers of glyceraldehyde has the -OH groups at the chiral center present far from carbonyl on the left side of the molecule. In D-form, glyceraldehyde has the -OH groups at the chiral center present far from carbonyl on the right side of the molecule.
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Chapter 6 Solutions
General, Organic, and Biological Chemistry (3rd Edition)
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