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
Pleas explain how this process occurs. Identify SN1, SN2, E2, E1, nucleophiles and electrophiles.
Rank the nucleophiles in following group in order of increasing nucleophilicity.
H2O, −OH, CH3CO2-
HCOO- > HO- > (CH3)2
Sort from best nucleophile to worst nucleophile
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
- 2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OHarrow_forwardWhich is the strongest nucleophile among the following? CN- , OH-, CH3OH, NH3arrow_forwardwhich of the following alkenes will most likely undergo a hydride shift when reacting with HCl?arrow_forward
- Choose all the nucleophiles OH- H3O+ NH4+ CH3OH (CH3)3CLi CH3CH2CH3 NaNH2 CH3SNaarrow_forwardThese are all electron-withdrawing groups that slow electrophilic aromatic substitution, with one exception. Which one? © CO,H O NO₂ O CF3 O NH2arrow_forwardWhich one of the following molecules CANNOT undergo a nucleophilic aromatic substitution reaction? o O2N. O,N `NO2 NO2 F NO2 NO2 NO2 NO2 `NO2 NO2 Brarrow_forward
- 9. Which of the following nucleophiles can undergo a substitution reaction with an alcohol under strongly acidic conditions? NH₂ - A B Br C D MgBrarrow_forwardH3C-C O: H ethanal :CN: and the electrophile is cyanide ion In the step you have just written, the nucleophile is slow rate-determining Ö—0—1 H3C-C-C=N; adductarrow_forwardExplain why quinuclidine is a much more reactive nucleophile thantriethylamine, even though both compounds have N atoms surroundedby three R groups.arrow_forward
- Which of the following species is likely to be a nucleophile and which an electrophile? (a) CH3CI {b) CH3S (c) N CH3 {d) N. CH3CHarrow_forwardList the following in increasing order of nucleophilic strength. CH3COO-, H2O, CH3O-, OH-, CH3CH20-arrow_forwardRank in terms of reactivity towards the nucleophile. 1=least 4=mostarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
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