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Chapter 11: 40E (page 350)

The following Walden cycle has been carried out. Explain the results, and indicate where Walden inversion occurs.

Short Answer

Expert verified

Inversion takes place in step 4.step4

Walden Inversion

Step by step solution

01

Walden inversion

It occurs in the reactions where the inversion of stereogenic carbon occurs.

02

Each step of the series to find inversion

  1. In step 1, when alcohol reacts with the potassium metal potassium alkoxide. Hence, no CO bond broken means no inversion occurs
  2. In step 2, the potassium alkoxide reacts with the alkyl halide to form ether

Then again, no CO bond break. The alkyl group replaces only potassium means no inversion occurs.

03

Each step of the series to find inversion

3. In step3, alcohol reacts with tosyl chloride, the OH bond is broken, and Ts replace h. Hence, no CO on break means no inversion occurs

4. In step4 –the OTs group is displaced, and then the CO bond is broken, and ether formation occurs. Hence, the inversion occurs.

Reaction showing Walden’s inversion

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Most popular questions from this chapter

Which reactant in each of the following pairs is more nucleophilic? Explain.

F)C≡N-or-OCH3

Question: Propose structures for compounds that fit the following descriptions:

(d) An alcohol that reacts rapidly with HCl at 0 °C

Question: Ignoring double-bond stereochemistry, what products would you expect from elimination reactions of the following alkyl halides? Which product will be the major product in each case?

Question:What products would you expect from the reaction of 1-bromopropane with each of the following?

(d) NaCN

Question:What products would you expect from the reaction of 1-bromopropane with each of the following?

(a) NaNH2
See all solutions

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