Organic Chemistry - Access
7th Edition
ISBN: 9780321820020
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 20, Problem 29P
Interpretation Introduction
Interpretation:
The type of transition state formed during Cope elimination has to be given.
Concept Introduction:
Cope elimination:
When tertiary
The nitrogen atom in the tertiary amine acts as a nucleophile and attacks an oxygen atom of peroxide that results in the formation of hydroxyl ammonium ion along with hydroxide ion, this ion under goes an elimination reaction to gives an
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Account for the following :(i) Primary amines (R-NH2) have higher boiling point than tertiary amines (R3N).(ii) Aniline does not undergo Friedel – Crafts reaction.(iii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
Which of the ff statements is false?
In aqueous solution the order of base strength R3N > R2NH > RNH2 > NH3.
Alkyl groups increase the electron density on nitrogen, making the amine more basic.
Alkyl groups stabilize the positive charge on the conjugate acid making the ammonium ion less acidic.
Solvation through H-bonding with water is more important in the conjugate acid than in the free amine.
Maraviroc, a drug used to treat HIV, is prepared by reductive amination of aldehyde A with amine B. What is the structure of maraviroc, if the most basic N atom of amine B is used in reductive amination?
Chapter 20 Solutions
Organic Chemistry - Access
Ch. 20.1 - Name the following:Ch. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Draw the product of each of the following...Ch. 20.5 - Prob. 6PCh. 20.5 - When pyrrole is added to a dilute solution of...Ch. 20.5 - Explain why cyclopentadiene (pKa = 15) is more...Ch. 20.6 - Prob. 10PCh. 20.6 - How to the mechanisms of the following reactions...Ch. 20.6 - Prob. 12P
Ch. 20.6 - Rank the following compounds from easiest to...Ch. 20.7 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.7 - Prob. 16PCh. 20.7 - Prob. 17PCh. 20.7 - Prob. 18PCh. 20.7 - Prob. 19PCh. 20.7 - Prob. 20PCh. 20 - Name the following:Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Which of the following compounds is easier to...Ch. 20 - Rank the following compounds from most reactive to...Ch. 20 - One of the following compounds undergoes...Ch. 20 - Benzene undergoes electrophilic aromatic...Ch. 20 - The dipole moments of furan and tetrahydrofuran...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - The chemical shifts of the C-2 hydrogen in the...Ch. 20 - Explain why protonating aniline has a dramatic...Ch. 20 - Prob. 33PCh. 20 - Propose a mechanism for the following reaction:Ch. 20 - Prob. 35PCh. 20 - Propose a mechanism for the following reactions:Ch. 20 - Prob. 37PCh. 20 - a. Draw resonance contributors to show why...Ch. 20 - Prob. 39PCh. 20 - Pyrrole reacts with excess...Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Organic chemists work with tetraphenylporphyrins...
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
- Arrange each group of compounds in order of increasing basicity.(a) CH3COO-, ClCH2COO-, and PhO- (b) sodium acetylide, sodium amide, and sodium acetate(c) sodium benzoate, sodium ethoxide, and sodium phenoxide (d) pyridine, sodium ethoxide, and sodium acetatearrow_forwardArrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.arrow_forwardSeveral additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitrocompounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds onecarbon atom. Show how these amine syntheses can be used for the following conversions. (c) 1@bromo@3@phenylheptane S 3@phenylheptan@1@amine (d) 1@bromo@3@phenylheptane S 4@phenyloctan@1@aminearrow_forward
- A. The water solubility of amines found in medications can be increased by salt formation. Dextromethorphan hydrobromide, a cough suppresant, is the salt formed from dextromethorphan (XX) and hydrobromic acid (HBr). Write the equation for the formation of dextromethorphan hydrobromide. B. Suggest appropriate starting materials ( amine and alkyl halide) needed for the preparation of each of the following salts: 1. Cetylpyridinium chloride 2. Benzyldimethyltetradecylammonium chloridearrow_forwardAliphatic amines are more basic than ammonia, whereas aromatic amines are less basic than ammonia. Is that true or false?arrow_forwardHow did Emil Bayer manage to make the bark of the willow tree that contained the active ingredient and precursor to aspirin LESS acidic via organic chemistry reaction. Be specific, show by chemical reaction and circle all functional groups (parts of the molecule) in the reactants that were altered in the products (circle these too).arrow_forward
- Primary amines can also be prepared by the reaction of an alkyl halide with azide ion, followed by catalytic hydrogenation. What advantage do this method and the Gabriel synthesis have over the synthesis of a primary amine using an alkyl halide and ammonia?arrow_forward1. Arrange the test samples in order of increasing reactivity with sodium bicarbonate? Explain briefly -Ethanoic acid, Butanoic acid, Benzoic acid 2. Arrange the test samples in order of increasing solubility in water? Explain briefly. -Ethylamine, Diethylamine, Aniline 3. Arrange the test samples in order of increasing basicity? Explain briefly. -NaOH, Ethylamine, Anilinearrow_forwardThe following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Of these three anticonvulsants, one is considerably more acidic than the other two. Which is the most acidic compound? Estimate its pKa and account for its acidity. How does its acidity compare with that of phenol? with that of acetic acid?arrow_forward
- Each pair of compounds below can be separatedusing acid/base extraction. Provide the common acid or base that could be used to effect the separation. Amines can be converted into ammonium salts using acid, but neutral amines are very weak acids (pKa~ 35)and thus cannot be extracted by an aqueous base.arrow_forwardArrange the following molecules in increasing order of acidity. Base it only on their structural differences and explain how it is so. 1. Butanoic acid, Propionic acid, Propylamine, Butanearrow_forwardRank each set of compounds in order of increasing basicity.pyrrole, imidazole, 3-nitropyrrolearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning