Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 9.2, Problem 4P
Why are NH3 and CH3NH2 no longer nucleophiles when they are protonated?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Good nucleophiles that are weak bases favor substitution overelimination. Explain this ?
Amines are good nucleophiles, even though they are neutral.
How would the rate of an SN2 reaction between an amine and an alkyl halide be affected if the polarity of the solvent is increased?
Would you expect acetate ion (CH3CO2 -) to be a better nucleophile in an SN2 reaction with an alkyl halide carried out in methanol or in dimethyl sulfoxide
Chapter 9 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 9.1 - Draw the structures of straight-chain alcohols...Ch. 9.1 - Prob. 2PCh. 9.1 - Prob. 3PCh. 9.2 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 9.2 - Prob. 5PCh. 9.2 - The observed relative reactivities of primary,...Ch. 9.4 - Which of the following alcohols would dehydrate...Ch. 9.4 - Prob. 10PCh. 9.4 - Prob. 11PCh. 9.4 - Prob. 12P
Ch. 9.4 - Prob. 13PCh. 9.5 - What product will be obtained from the reaction of...Ch. 9.5 - Prob. 15PCh. 9.6 - a. What is each ethers systematic name? 1....Ch. 9.8 - Draw the structure of the following: a....Ch. 9.8 - Prob. 20PCh. 9.8 - Would you expect the reactivity of a five-membered...Ch. 9.9 - Explain why the two arene oxides in Problem 22...Ch. 9.9 - Which compound is more likely to be...Ch. 9.11 - The following three nitrogen mustards were studied...Ch. 9 - What are the common and systematic names of the...Ch. 9 - Prob. 28PCh. 9 - Prob. 29PCh. 9 - Prob. 30PCh. 9 - Prob. 31PCh. 9 - What is the major product obtained from the...Ch. 9 - Draw structures for the following: a....Ch. 9 - Prob. 34PCh. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Prob. 37PCh. 9 - Ethylene oxide reacts readily with HO.because of...Ch. 9 - Propose a mechanism for each of the following...Ch. 9 - Which of the following ethers would be obtained in...Ch. 9 - Show how each of the following syntheses could be...Ch. 9 - Prob. 42PCh. 9 - Prob. 43PCh. 9 - Prob. 44PCh. 9 - Propose a mechanism for each of the following...Ch. 9 - a. Propose a mechanism for the following reaction:...Ch. 9 - Three arene oxides can be obtained from...Ch. 9 - Prob. 48PCh. 9 - The following reaction takes place several times...Ch. 9 - Show how each of the following compounds could be...Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - What alkenes would you expect to be obtained from...Ch. 9 - Triethylenemelamine (TEM) is an antitumor agent....Ch. 9 - When a diol that has OH groups on adjacent carbons...Ch. 9 - What product is obtained when...Ch. 9 - Prob. 58P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
Given the following compounds:
Which is the most reactive towards a nucleophile?
Which will form a yellow precipitate with I2 and NaOH?
arrow_forward
The compound below has multiple electrophilic sites which could potentially react with an organolithium reagent, like phenyllithium. If only 1 mole of Phli is added for each mole of starting material, which atom is most likely to be attacked by the nucleophile?
arrow_forward
Which of the following could act as a nucleophile?
A) HCl
B) CH3NH2
C) BF3
D) CH3Br
arrow_forward
Rank the primary, secondary, tertiary, and aryl halides in terms of reactivity with the nucleophile. Which type of halide react faster by an SN2 reaction? Explain
arrow_forward
Which solvent would make the bromination through electrophilic aromatic substitution faster?
Pentane
Toluene
Propanoic acid
Petroleum ether
arrow_forward
Explain the observed rate of reactivity of the following 2° alkyl halides in an SN1 reaction.
arrow_forward
Which species is likely to undergo a reaction with the nucleophile readily? A. (ch3)3cl
b. (Ch3)2HCI
c. Ch3ch2cl
d. CH3CI
arrow_forward
What is the strongest nucleophile, NH3, CH4, CH3O-, or H2O?
arrow_forward
For each pair, predict the stronger nucleophile in the SN2 reaction (using an alcohol asthe solvent). Explain your prediction.(a) (CH3CH2)3N or (CH3CH2)2NH
arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY