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Magazine Chapter 4: Q40P (page 166)
The stereoisomer of cholesterol found in nature is shown here.
a. How many asymmetric centers does cholesterol have?
b. What is the maximum number of stereoisomers that cholesterol can have?
Short Answer
a. 8
b. 256
Step by step solution
Definition of asymmetric centre-
A symmetric carbon atom is one that comprises four separate atoms or groups of atoms (substituents) bound to it in an organic complex.
It is denoted by an astric (*) symbol.
The number of stereoisomers that can exist is 2n, where n is the number of asymmetric centres.
a) The sp3 carbons that are bound to four different substituents must be found.
Four distinct substituents which are attached to sp3 carbons is called a symmetrical centre.
The eight asymmetric centres of cholesterol are depicted by arrows
b)- Calculating the maximum number of stereoisomers that cholesterol can have-
The number of stereoisomers that can exist is 2n, where n is the number of asymmetric centres.
No of asymmetric centers= 8
Total number of stereoisomers= 28= 256
The above number of stereoisomers are found in nature.
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