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Ch.20 Carbohydrates
Chapter 20, Problem 20.5

Aldoheptoses have five chiral carbon atoms. What is the maximum possible number of aldoheptose stereoisomers? Draw all of the aldoheptose stereoisomers.

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1
Identify the number of chiral centers in the molecule. Aldoheptoses have five chiral carbon atoms.
Use the formula for calculating the maximum number of stereoisomers: \(2^n\), where \(n\) is the number of chiral centers.
Substitute the number of chiral centers into the formula: \(2^5\).
Calculate the result of \(2^5\) to determine the maximum number of stereoisomers.
To draw all stereoisomers, consider each chiral center can have two configurations (R or S), and systematically vary each configuration to generate all possible combinations.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Chirality

Chirality refers to the geometric property of a molecule having non-superimposable mirror images, much like left and right hands. In organic chemistry, chiral centers are typically carbon atoms bonded to four different substituents. The presence of chiral centers in a molecule leads to the existence of stereoisomers, which are compounds that differ in the spatial arrangement of atoms.
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Chirality Example 1

Stereoisomers

Stereoisomers are compounds that have the same molecular formula and connectivity of atoms but differ in the arrangement of their atoms in space. The number of stereoisomers for a compound can be calculated using the formula 2^n, where n is the number of chiral centers. This concept is crucial for understanding the diversity of molecular structures that can arise from a single chemical formula.
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Stereoisomers Concept 2

Aldoheptoses

Aldoheptoses are a type of monosaccharide with seven carbon atoms and an aldehyde group. They are characterized by their specific structural features, including the presence of chiral centers. Understanding the structure of aldoheptoses is essential for determining the number of possible stereoisomers, as each chiral center can contribute to the overall stereochemical diversity of the molecule.