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Chapter 18: 18-12P (page 677)

a. Draw resonance structures for the carbocation formed after loss of a leaving group from phytyl diphosphate.

b. Draw the two-step mechanism for Friedel–Crafts alkylation of 1,2-dihydroxynaphthoic acid with this carbocation to form X.

Short Answer

Expert verified

The Friedel-Craft is of two types, alkylation, and acylation. The alkylation proceeds via theelectrophile generation and acylation proceeds via the direct attack on the carbonyl carbon of the acyl group.

Step by step solution

01

Friedel-Crafts reaction

The Friedel-Craft is of two types, alkylation, and acylation. The alkylation proceeds via theelectrophile generation and acylation proceeds via the direct attack on the carbonyl carbon of the acyl group.

02

Explanation

a. The elimination of the leaving group \(^ - {\rm{OPP}}\) generates an allyl carbocation which can form another resonance structure (tertiary carbocation) as:

b. The two-step mechanism is the substitution of carbocation of diphytyl diphosphate and the abstraction of the proton as:

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Most popular questions from this chapter

Question: Explain the following observation. Ethyl 3-phenylpropanoate (C6H5CH2CH2CO2CH2CH3) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5=CHCO2CH2CH3) reacts with electrophiles to afford meta-disubstituted arenes.

Question: What is the major product of electrophilic addition of HBr to the following alkene? Explain your choice.


Question: Draw a stepwise, detailed mechanism for the following intramolecular reaction.

Label each compound as more or less reactive than benzene in electrophilic aromatic substitution.

Question: Friedel-Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene.

  1. How many stereogenic centers are present in the product?
  2. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.
See all solutions

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