Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Textbook Question
Chapter NW2, Problem 1CTQ
A student names the second structure above 2,3-dimethylcyclohex-1-ene. What rule does thisviolate?
Expert Solution & Answer
Interpretation Introduction
Interpretation:The rules violate by the student during naming of thegiven structure as 2, 3-dimethylcyclohex-1-ene needs to be determined.
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 −
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.
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.
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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Students have asked these similar questions
. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the
molecule depicted below.
Bond B
2°C. +2°C. < cleavage
Bond A
• CH3 + 26. t cleavage
2°C• +3°C•
Bond C
Cleavage
CH3 ZC
'2°C. 26.
E
Strongest
3°C. 2C.
Gund
Largest
BDE
weakest bond
In that molecule
a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in
appropriate boxes.
Weakest
C bond
Produces
A
Weakest
Bond
Most
Strongest
Bond
Stable radical
Strongest Gund
produces least stable
radicals
b. (4pts) Consider the relative stability of all cleavage products that form when bonds A,
B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B,
and C are all carbon radicals.
i. Which ONE cleavage product is the most stable? A condensed or bond line
representation is fine.
人
8°C. formed in
bound C
cleavage
ii. Which ONE cleavage product is the least stable? A condensed or bond line
representation is fine.
methyl radical
•CH3
formed in
bund A Cleavage
Which carbocation is more stable?
Are the products of the given reaction correct? Why or why not?
Chapter NW2 Solutions
Organic Chemistry: A Guided Inquiry
Ch. NW2 - A student names the second structure above...Ch. NW2 - Prob. 2CTQCh. NW2 - Name each of the following alkenes:Ch. NW2 - Draw the following alkenes: a....Ch. NW2 - Prob. 5CTQCh. NW2 - Prob. 6CTQCh. NW2 - Prob. 7CTQCh. NW2 - Prob. 8CTQCh. NW2 - Prob. 9CTQCh. NW2 - Prob. 10CTQ
Ch. NW2 - Instead of using the ending “ol,” an OH can be...Ch. NW2 - Prob. 12CTQCh. NW2 - Prob. 13CTQCh. NW2 - Prob. 14CTQCh. NW2 - Prob. 15CTQCh. NW2 - Prob. 16CTQCh. NW2 - Prob. 17CTQCh. NW2 - Prob. 18CTQCh. NW2 - Prob. 19CTQCh. NW2 - Prob. 20CTQCh. NW2 - Prob. 21CTQCh. NW2 - Prob. 1ECh. NW2 - Prob. 2E
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