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Chapter 18: Q.10P (page 577)

What product would you expect from Claisen rearrangement of 2-butenyl phenyl ether?

Short Answer

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Answer

The product expected from Claisen rearrangement of 2-butenyl phenyl ether is,

Step by step solution

01

Step-by-Step SolutionStep 1: Claisen rearrangement

In Claisen rearrangement, new C-C bonds are formed by Claisen [3,3], and after re-aromatization, phenol product is formed.

02

Formation of TS and intermediate

A transition state with new C-C bonds formation and intermediate with enone formation forms.

03

The product expected from Claisen rearrangement of 2-Butenyl phenyl ether

In rearrangement, the ether with the groups is drawn and positioned so that they will appear in the product. The six bonds can either be broken or formed in the product and are shown by dash lines in the transition state. The bonds are redrawn at the intermediate enone, which is again rearranged to form a more stable phenol.

Claisen rearrangement of 2-Butenyl phenyl ether

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Most popular questions from this chapter

Treatment of trans-2-chlorocyclohexanol with NaOH yields 1,2-epoxycyclohexane,but reaction of the cis isomer under the same conditionsyields cyclohexanone. Propose mechanisms for both reactions, andexplain why the different results are obtained.

Question: tert-Butyl ethers can be prepared by the reaction of an alcohol with2-methylpropene in the presence of an acid catalyst. Propose a mechanismfor this reaction

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The red fox (Vulpesvulpes) uses a chemical communication system based on scent marks in urine. One component of fox urine is a sulfide whose mass spectrum has M+=116. IR spectroscopy shows an intense band at 890鈥�cm鈭�1and 1HNMR spectroscopy reveals the following peaks:

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How could you prepare benzyl phenyl ether from benzene and phenol? More than one step is required.
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