(a) Write structural formulas and provide IUPAC names for all the isomeric
(b) Which of the isomers in part (a) yield chiral alcohols on reaction with sodium borohydride?
(c) Which of the isomers in part (a) yield chiral alcohols on reaction with methylmagnesium iodide?
Interpretation:
The given parts are to be explained.
Concept Introduction:
The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of the organic compound is correctly interpreted from its name.
Rules for writing the structural formula from IUPAC are as follows:
First, identify the word root for the given compound.
The suffix used in the compound like
The position and location of the substituents that are bonded to the carbon chain must
identified and number theses substituents on the basis of their priorities.
Answer to Problem 23P
Solution:
a)
b)
c)
Explanation of Solution
a) Structural formulas and IUPAC name of the isomeric aldehydes and ketones of
The constitutional isomers are the isomers that consist of the same chemical formula but the way they attach to their atoms are totally different from each other.
Aldehydes and ketones contain carbonyl
b) The isomers that form chiral alcohols on the reaction with sodium borohydride.
The reduction of aldehydes with sodium borohydride results in the formation of a primary alcohol, whereas in ketones the formation of secondary alcohols is taken place. Primary alcohols are not chiral in nature. On the other hand, the secondary alcohols that are formed from unsymmetrical ketones show chirality. Therefore, among the isomers in part (a),
c) The isomers that give chiral alcohols on reaction with methylmagnesium iodide.
Methylmagnesium iodide is also known as the Grignard reagent. Aldehydes can give chiral alcohols on reaction with methylmagnesium iodide. The formation of chiral and achiral molecules from the isomers that are present in part(a) are shown as:
Hence, the isomers that form chiral alcohols on reaction with methylmagnesium iodide are shown below.
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Chapter 18 Solutions
Organic Chemistry - Standalone book
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