Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter NW2, Problem 1CTQ

A student names the second structure above 2,3-dimethylcyclohex-1-ene. What rule does thisviolate?

Expert Solution & Answer
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Interpretation Introduction

Interpretation:The rules violate by the student during naming of thegiven structure as 2, 3-dimethylcyclohex-1-ene needs to be determined.

  Organic Chemistry: A Guided Inquiry, Chapter NW2, Problem 1CTQ , additional homework tip  1

Concept introduction:

The chemical name of the compound can be defined as the name of each element or sub-compounds which are present in the chemical composition of the compound.

Answer to Problem 1CTQ

The rule of branching in the ring is violated by the student. Therefore, the name of the compound is 1, 6-dimethylcyclohexane.

Explanation of Solution

The structure of the compound is given as −

  Organic Chemistry: A Guided Inquiry, Chapter NW2, Problem 1CTQ , additional homework tip  2

The student named the above compound as 2, 3-dimethylcyclohex-1-ene. It is to be determined that the name given by the student is correct or not. Label all the carbon atoms which are present in the ring structure to determine that the name of the compound is correct or not. The parent chain is numbered in such a way to give the lowest possible number to the double bond and these two numbers will be placed before the suffix.

  Organic Chemistry: A Guided Inquiry, Chapter NW2, Problem 1CTQ , additional homework tip  3

In the compound structure, the carbon with double bond should have lowest number because it has the greatest number of branches. Therefore, the numbering of the atom will start with the double bonded carbons which have methyl substituent.

  Organic Chemistry: A Guided Inquiry, Chapter NW2, Problem 1CTQ , additional homework tip  4

Hence, the compound will be named as 1,6-dimethylcyclohexane. In this rule of the branching in a ring containing double bond is violated by the student.

Conclusion

Thus, the student violated the rule of branching in the ring. Hence the name of the structure is 1,6-dimethylcyclohexane.

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