Question

Which of these structures has the most angle strai

Which of these structures has the most steric strain?
Which of these structures has the most torsional (eclipsing) strain?
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Answer #1
Concepts and reason

The deviation from ideal values of bond angles and bond lengths determines strain in a molecule. Three types of strain are angle strain, steric strain, and torsional strain.

Fundamentals

Angle strain in a molecule is determined by the Baeyer’s strain theory. Deviation from actual tetrahedral bond angle is the reason for the angle strain.

Steric effect is determined by the interaction between the substituent. If the bulky groups are in close proximity of each other then, the compound will be unstable due to overcrowding of the substituents.

Torsional strain is determined by the repulsion between the bonding pair of electrons. It is also known as eclipsing strain as it is also present in the molecule having eclipsing conformation due to overcrowding of the electron pair on the substituents. Due to torsional strain the potential energy of the conformation increases.


(a)


‎Draw the structure of the given compounds and mark the bond angle in each case as shown below:

H
900
120
Hl
109.5°
1,1,3,3,5,5
hexamethylcyclohexane
1,1-dimethylcyclobutane
staggered butane

The molecule having maximum angle strain is 1,1-dimethylcyclobutane
.

(b)

Draw the structure of the given compounds and show the interaction between the bulky substituents as shown below:

Н
Н
H
Н
1,1,3,3,5,5-
hexamethylcyclohexane
1,1-dimethylcyclobutane
staggered butane
symbol used to show the interaction betwe

The molecule having maximum steric strain is 1,1,3,3,5,5-hexamethylcyclohexane
.

(c)

Draw the given structure of substituted cyclohexane ring and marked the position of substituents as shown below:

Н
НС.
Н
H
н
CH3
H
Н
staggered butane
1,1-dimethylcyclobutane
staggered butane
1,1,3,3,5,5-
hexamethylcyclohexane

Hence, the molecule having the maximum torsional strain is .

Ans: Part (a)

1,1-dimethylcyclobutane
1,1,3,3,5,5-hexamethylcyclohexane
staggered butane

Part (b)

1,1-dimethylcyclobutane
1,1,3,3,5,5-hexamethylcyclohexane
staggered butane

Part (c)

1,1-dimethylcyclobutane
1,1,3,3,5,5-hexamethylcyclohexane
staggered butane

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