Solution Found!
Trans-1,4-di-tert-butylcyclohexane exists in a normal chair conformation
Chapter 2, Problem 2.36(choose chapter or problem)
Trans-1,4-di-tert-butylcyclohexane exists in a normal chair conformation. Cis-1,4-di-tert-butylcyclohexane, however, adopts a twist-boat conformation. Draw both isomers andexplain why the cis isomer is more stable in a twist-boat conformation.
Questions & Answers
QUESTION:
Trans-1,4-di-tert-butylcyclohexane exists in a normal chair conformation. Cis-1,4-di-tert-butylcyclohexane, however, adopts a twist-boat conformation. Draw both isomers andexplain why the cis isomer is more stable in a twist-boat conformation.
ANSWER:Key concepts
Chair conformation
The most stable conformation of a cyclohexane ring; all bond angles are close to 109.5°, and all bonds on adjacent carbons are staggered.
Boat conformation
A nonplanar conformation of a cyclohexane ring in which carbons 1 and 4 of the ring are bent toward each other
Twist-boat conformation
A nonplanar conformation of a cyclohexane ring that is twisted from and slightly more stable than a boat conformation
Cis,trans isomers
Stereoisomers that have the same connectivity but a different arrangement of their atoms in space as a result of the presence of either a ring or a carbon-carbon double bond.
Cis - same side
Trans - opposite side
Step 1 of 3
Here first we have to draw
Trans-1,4-di-tert-butylcyclohexane in normal chair conformation and
Cis-1,4-di-tert-butylcyclohexane in twist-boat conformation
Also explain why the cis isomer is more stable in a twist-boat conformation.
Twist-boat conformation - A nonplanar conformation of a cyclohexane ring that is twisted from and slightly more stable than a boat conformation.
Chair conformation - The most stable conformation of a cyclohexane ring; all bond angles are close to 109.5°, and all bonds on adjacent carbons are staggered.