Skip to main content
Ch. 7 - Structure and Synthesis of Alkenes; Elimination
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 7 - Structure and Synthesis of Alkenes; EliminationProblem 7e
Chapter 7, Problem 7e

The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.
e. 2,5-dimethylcyclohexene

Verified step by step guidance
1
Identify the given name: 2,5-dimethylcyclohexene. This suggests a cyclohexene ring with methyl groups at positions 2 and 5.
Draw a cyclohexene ring, which is a six-membered carbon ring with one double bond. The double bond should be between two adjacent carbon atoms.
Number the carbon atoms in the cyclohexene ring starting from one of the carbons in the double bond, ensuring the lowest possible numbers for substituents.
Place methyl groups on the cyclohexene ring at the specified positions (2 and 5) according to the given name.
Check the structure for the correct IUPAC naming: Ensure the double bond has the lowest possible locant and adjust the numbering if necessary. Provide the correct name based on the structure drawn.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4m
Was this helpful?

Key Concepts

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

IUPAC Nomenclature

IUPAC nomenclature is a standardized system for naming chemical compounds. It ensures that each compound has a unique name, which reflects its structure. Understanding the rules of IUPAC nomenclature is crucial for identifying errors in chemical names and correcting them, such as ensuring the correct numbering of carbon atoms in a cycloalkene.
Recommended video:
Guided course
03:43
The different parts of an IUPAC name

Cycloalkenes

Cycloalkenes are cyclic hydrocarbons containing one or more double bonds within the ring structure. The presence of a double bond affects the numbering of the carbon atoms, as the double bond should receive the lowest possible numbers. Recognizing the structure of cycloalkenes is essential for correctly naming and drawing them.
Recommended video:
Guided course
01:11
How to find the root name for cycloalkanes

Substituent Positioning

Substituent positioning involves identifying and numbering the location of groups attached to the main carbon chain or ring. In cycloalkenes, substituents should be numbered to give the lowest possible numbers, considering the position of the double bond. Correctly identifying substituent positions is key to correcting the name of a compound like 2,5-dimethylcyclohexene.
Recommended video:
4:06
Reactions at the Allylic Position Example 3
Related Practice
Textbook Question

The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.

a. cis-dimethylpent-2-ene

b. 3-vinylhex-4-ene

2
views
Textbook Question

For each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.

b. 1-bromo-1-methylcyclohexane + triethylamine(Et3N:)

Textbook Question

Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.

a. 3-bromo-2-chloropent-2-ene

b. 3-ethylhexa-2,4-diene

Textbook Question

The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.

c. 2-methylcyclopentene

d. 6-chlorocyclohexadiene

1
views
Textbook Question

Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.

c. 3-bromo-2-methylhex-3-ene

d. penta-1,3-diene

Textbook Question

Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.

e. 3-ethyl-5-methyloct-3-ene

f. 3,7-dichloroocta-2,5-diene