/*! 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} Q6P Rank each set of compounds in or... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 19: Q6P (page 988)

Rank each set of compounds in order of increasing basicity

(a) NaOH, NH3, CH3NH2, Ph-NH2

(b) aniline, p-methylaniline, p-nitroaniline

(c) aniline, pyrrole, pyridine, piperidine

(d) pyrrole, imidazole, 3-nitropyrrole

Short Answer

Expert verified

(a)

Basicity (pKb) of NaOH is 0.2

Basicity (pKb) of NH3 is 4.74

Basicity (pKb) of CH3NH2 is 3.38

Basicity (pKb) of Ph-NH2 is 9.38

Order of increasing basicity = Ph-NH2 < NH3 <CH3NH2 < NaOH

(b)

Basicity (pKb) of aniline is 9.38

Basicity (pKb) of p-methylaniline is 9.21

Basicity (pKb) of p-nitroaniline is 12.99

Order of increasing basicity = p-nitroaniline< aniline < p-nitroaniline

(c)

Basicity (pKb) of aniline is 9.38

Basicity (pKb) of pyrrole is 13.6

Basicity (pKb) of pyridine is 8.77

Basicity (pKb) of piperidine is 4

Order of increasing basicity = pyrrole < aniline < pyridine < piperidine

(d)

Basicity (pKb) of pyrrole is 13.6

Basicity (pKb) of imidazole is 7.0

3-nitropyrrole is formed by adding nitric acid to pyrrole i.e. nitration of pyrrole group.

Therefore it is less basic than pyrrole.

Order of increasing basicity = 3-nitopyrrole< pyrrole < imidazole

Step by step solution

01

Concept

pKb is the negative base -10 loh of the base dissociation constant (Kb) of the solution, which is used to determine the strength of base. Lower pkb value indicates a stronger base.

02

(a) NaOH, NH3, CH3NH2, Ph-NH2:

Basicity (pKb) of NaOH is 0.2

Basicity (pKb) of NH3 is 4.74

Basicity (pKb) of CH3NH2 is 3.38

Basicity (pKb) of Ph-NH2 is 9.38

Order of increasing basicity = Ph-NH2 < NH3 <CH3NH2 < NaOH

03

(b)  aniline, p-methylaniline, p-nitroaniline

Basicity (pKb) of aniline is 9.38

Basicity (pKb) of p-methylaniline is 9.21

Basicity (pKb) of p-nitroaniline is 12.99

Order of increasing basicity = p-nitroaniline< aniline < p-nitroaniline

04

(c) aniline, pyrrole, pyridine, piperidine

Basicity (pKb) of aniline is 9.38

Basicity (pKb) of pyrrole is 13.6

Basicity (pKb) of pyridine is 8.77

Basicity (pKb) of piperidine is 4

Order of increasing basicity = pyrrole < aniline < pyridine < piperidine

05

(d) pyrrole, imidazole, 3-nitropyrrole

Basicity (pKb) of pyrrole is 13.6

Basicity (pKb) of imidazole is 7.0

3-nitropyrrole is formed by adding nitric acid to pyrrole i.e. nitration of pyrrole group.

Therefore it is less basic than pyrrole.

Order of increasing basicity = 3-nitopyrrole< pyrrole < imidazole

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

Predict the products of the following reactions:

(a) 别虫肠别蝉蝉鈥夆赌塏贬3鈥夆赌�+鈥夆赌塒h鈭�CH2CH2CH2Br鈫�

(b)1鈭�bromopentane鈫�(2)LiAlH4(3)H3O+(1)NaN3

(c)

(d) product鈥夆赌塮rom鈥夆赌塸art鈥夆赌塩鈫�heat

(e)

(f) product鈥夆赌塮rom鈥夆赌塸art鈥夆赌塭鈫�(3)heat(1)excessCH3I(2)Ag2O

(g)

(h)

(i)

(j) product鈥夆赌塮rom鈥夆赌塸art鈥夆赌塱鈫�(2)H3O+(1)LiAlH4

(k)

(l)

Predict the products from the reactions of the following amines with sodium nitrite in dilute.

  1. Cyclohexanamine
  2. N-ethylhexan-2-amine
  3. Piperidine
  4. Aniline

(a) Show how fragmentation occurs to give the base peak at m/z 58 in the mass spectrum of ethyl propyl amine (N-ethylpropan-1-amine), shown below.

(b) Show how a similar cleavage in the ethyl group gives an ion of m/z72.

(c) Explain why the peak at m/z 72 is much weaker than the one at m/z 58.

Question. The carbon NMR chemical shifts of diethylmethylamine, piperidine, propan-1-ol, and propanal follow. Determine which spectrum corresponds to each structure, and show which carbon atom(s) are responsible for each absorption.

(a) 25.9, 27.8, 47.9

(b) 12.4, 41.0, 51.1

(c) 7.9, 44.7, 201.9

(d) 10.0, 25.8, 63.6

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
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Nuclear Chemistry

Read Explanation

Physical Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Kinetics

Read Explanation

Ionic and Molecular Compounds

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.