Why does t-butyl chloride undergoe solvolysis in 70% water/30% acetone at a rate slower than in 80% water/20% acetone?

Answer 1

The more polar solvent is better at stabilizing the developing carbocation.

The solvolysis of t-butyl chloride is an #"S"_"N"1#reaction. It involves the formation of a 3° carbocation in a slow first step.

A polar solvent solvates and helps to stabilize the developing carbocation. This lowers the energy of the transition state and speeds up the reaction.

The greater the percentage of water in this solvent mixture, the more polar the solvent. The more polar the solvent, the better it is at solvating the developing carbocation and lowering the activation energy.

An 80:20 water/acetone mixture is more polar than a 70:30 mixture, so the solvolysis is faster in the more water-rich solvent.

Sign up to view the whole answer

By signing up, you agree to our Terms of Service and Privacy Policy

Sign up with email
Answer 2

Tertiary butyl chloride (t-butyl chloride) undergoes solvolysis slower in a 70% water/30% acetone solvent mixture compared to an 80% water/20% acetone mixture due to the polarity of the solvent. The 70% water/30% acetone mixture is less polar than the 80% water/20% acetone mixture, which affects the rate of solvolysis. Since t-butyl chloride is less soluble in the less polar solvent mixture, the nucleophilic attack by water molecules, necessary for the solvolysis reaction, occurs less frequently, leading to a slower rate of reaction.

Sign up to view the whole answer

By signing up, you agree to our Terms of Service and Privacy Policy

Sign up with email
Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

Not the question you need?

Drag image here or click to upload

Or press Ctrl + V to paste
Answer Background
HIX Tutor
Solve ANY homework problem with a smart AI
  • 98% accuracy study help
  • Covers math, physics, chemistry, biology, and more
  • Step-by-step, in-depth guides
  • Readily available 24/7