/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q64P Show how the substituents contai... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 19: Q64P (page 1037)

Show how the substituents containing the azo group () can facilitate both electrophilic and nucleophilic aromatic substitution.

A.Hafner and S.Brase, Angewandte Chemie Int. Ed., M.Heinrich et al., Journal of Organic Chemistry, 2012, 77, 1520. 2012, 51, 3713

Short Answer

Expert verified

Attack of electrophile on the given system leads to extensive delocalization of positive charge which stabilizes the intermediate from the electrophilic attack. Positive charge on nitrogen of azo group also occurs in two of the resonance forms and this positive charge on nitrogen atom is stable as octet of nitrogen is complete in these structures. Delocalisation of charge brings stability to the overall system.

Delocalization of positive charge stabilises the system

Delocalisation of positive charge stabilises the system

Step by step solution

01

Step-1. Explanation of part (a):

Attack of electrophile on the given system leads to extensive delocalization of positive charge which stabilizes the intermediate from the electrophilic attack. Positive charge on nitrogen of azo group also occurs in two of the resonance forms and this positive charge on nitrogen atom is stable as octet of nitrogen is complete in these structures. Delocalisation of charge brings stability to the overall system.

Delocalization of positive charge stabilises the system

Delocalisation of positive charge stabilises the system

02

Step-2. Explanation of part (b)

Attack of nucleophile on the system leads to extensive delocalization of negative charge which stabilizes the intermediate from nucleophilic attack. In two of the resonance forms, negative charge occurs on one one of the nitrogen of azo group, and negative charge also occurs on oxygen and we know that, negative charge on electronegative atom is stable. Thus, due to delocailsation of negative charge, stability in the overall system arises.

Delocalisation of negative charge stabilizes the system

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91影视!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

(A true story.) A drug user responded to an ad placed by a DEA informant in a drug-culture magazine. He later flew from Colorado to Maryland, where he bought some 1-phenyl-2-propanone (P2P) from the informant. The police waited nearly a month for the suspect to synthesize something, then obtained a search warrant, and searched the residence. They found the unopened bottle of P2P; apparently, the suspect was not a good chemist and was unable to follow the instructions the informant gave him. They also found pipes and bongs with residues of marijuana and cocaine, plus a bottle of methylamine hydrochloride, some muriatic acid (dilute HCL), zinc strips, flasks, and other equipment.

(a) Assume you are consulting for the police. Show what synthesis the suspect was prepared to carry out, to provide probable cause for the charge of attempting to manufacture a controlled substance.

(b) Assume you are a member of the jury. Would you convict the defendant of attempting to manufacture a controlled substance?

a) Guanidine (shown) is about as strong base as hydroxide ion. Explain why guanidine is a much stronger base than most other amines.

(b) Show why p-nitroaniline is a much weaker base (3 pKb units weaker) than aniline.

(c) Explain why N,N-2,6-tetramethylaniline (shown) is a much stronger base than N,N-dimethylaniline.

The two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides. Show how these techniques can be used to accomplish the following syntheses.

(a) benzoic acid to benzylamine

(b) benzaldehyde to benzylamine

(c) pyrrolidine to N-ethylpyrrolidine

(d) cyclohexanone to N- cyclohexylpyrrolidine

(e) HOOC-(CH2)3 -COOH to pentane-1,5-diamine cadaverine

A compound of formula C11H16N2gives the IR, 1HNMR, and 13CNMR spectra shown. The proton NMR peak at未 2.0disappears on shaking with D2O. Propose a structure for this compound, and show how your structure accounts for the observed absorptions.

What would happen in the synthesis of sulfanilamide if the amino group were not protected as an amide in the chlorosulfonation step?
See all solutions

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Read Explanation

Physical Chemistry

Read Explanation

Kinetics

Read Explanation

Chemistry Branches

Read Explanation

Chemical Analysis

Read Explanation

Inorganic Chemistry

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.