Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22.4, Problem 7P
Interpretation Introduction
Interpretation:
Considering the resonance structure, the reason that the given compounds are weaker base than aniline corresponding to the effect of the substituent is to be explained.
Concept Introduction:
>The major factors that contribute to the basic strength are
The high percentage of
An acidic substance in a reaction donates a proton, while a base in a reaction accepts a proton.
>The elimination of a proton leads to the formation of a conjugate base. If the base accepts a proton the species formed is known as conjugate acid.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
MeO
22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone
is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an
acetoacetic ester synthesis (Section 19.6).
5
3
6
CH₂O
CI
acetoacetic
ester
synthesis
HC
7
MeO
MeO
1
8
2-Methoxynaphthalene
Nabumetone
(a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at
carbon 5 or 7.
(b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum-
etone is completed.
18.26 Synthesize each of the following compounds from diethyl malonate or ethyl acetoacetate and any other organic and inorganic reagents.
(a)
(c)
(e)
OH
(b)
OH
(d)
(f)
Problem 25.14 What nitro compound, nitrile, and amide are reduced to each compound?
a. CH,CHCH,NH,
CH,NH,
b.
Problem 25.15 What amine is formed by reduction of each amide?
CONH,
b.
"NHCH
Problem 25.16 Explain why isopropylamine [(CH).CHNH] can be prepared by reduction of a nitro compound, but
cannot be prepared by reduction of a nitrile, even though it is a 1* amine.
Problem 25.17 Which amines cannot be prepared by reduction of an amide?
NH
O O D
Chapter 22 Solutions
Organic Chemistry - Standalone book
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.4 - Prob. 5PCh. 22.4 - Prob. 6PCh. 22.4 - Prob. 7PCh. 22.4 - Prob. 8PCh. 22.4 - Prob. 9PCh. 22.7 - Prob. 10P
Ch. 22.8 - Problem 22.11 Three of the following amines can be...Ch. 22.9 - Prob. 12PCh. 22.10 - Prob. 13PCh. 22.13 - Prob. 14PCh. 22.14 - Prob. 15PCh. 22.15 - Prob. 16PCh. 22.15 - Prob. 17PCh. 22.17 - Prob. 18PCh. 22.17 - Prob. 19PCh. 22.17 - Prob. 20PCh. 22.17 - Prob. 21PCh. 22.18 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Arrange the following compounds or anions in each...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - The compound shown is a somewhat stronger base...Ch. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Write the structure of the product formed on...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - Devise efficient syntheses of each of the...Ch. 22 - Prob. 46PCh. 22 - Prob. 47PCh. 22 - Prob. 48PCh. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - Prob. 52PCh. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56DSPCh. 22 - Prob. 57DSPCh. 22 - Prob. 58DSPCh. 22 - Prob. 59DSPCh. 22 - Synthetic Applications of Enamines The formation...Ch. 22 - Prob. 61DSP
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
- 19.60 Draw the major organic products for each of the following reactions. (a) (b) OEt LOCH3 Pd(PPH3)4, NaOH EtO Pd(PPh)4, NaOH -? THE THE (c) (d) Pd(OAc)2 Pd(OAc)2. ? PPH3,EtgN ? PPH3,EtgN Brarrow_forwardProblem 19.22 Show how ethyl bromide can be used as a starting material in the preparation of each of the following compounds. (Hint: How are Grignard reagents prepared?) HO `CH;CH3 (a) OH (b) OH (c) 1-butanol (d) PHCHCH,CH; (CH;CH;),CCH3arrow_forward18.4 Draw a structure corresponding to each name: (a) N-methylaniline; (b) m-ethylaniline; (c) 3,5-diethylaniline; (d) N,N-diethylaniline.arrow_forward
- Propose a reasonable synthesis of the following reaction:.arrow_forwardOctinoxate is an unsaturated ester used as an active ingredient in sunscreens. (a) What carbonyl compounds are needed to synthesize this compound using a condensation reaction? (b) Devise a synthesis of octinoxate from the given organic starting materials and any other needed reagents.arrow_forwardRank the following compounds in order of increasing basicity in aqueous solution, least basic first a) Propylamine, ammonium, dipropylamine b) Methyl-3-aminopropanoate, sectutylamine, NH3*CH2CH2NH2 c) Aniline, methyl m-aminobenzoate,, methy! p-aminobenzoatearrow_forward
- Problem 25.15 What amine is formed by reduction of each amide? CONH, NHCH, O O Darrow_forwardDevise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel (Section 18.15C).arrow_forward20.58 Fluphenazine is an antipsychotic drug that is administered as an ester prodrug via intramuscular injection: CF3 Fluphenazine decanoate The hydrophobic tail of the ester is deliberately designed to enable a slow release of the prodrug into the bloodstream, where the prodrug is rapidly hydrolyzed to produce the active drug. (a) Draw the structure of the active drug. (b) Draw the structure of and assign a systematic name for the carbox- ylic acid that is produced as a by-product of the hydrolysis step.arrow_forward
- Devise a synthesis of anastrozole, a drug used to reduce the recurrence of breast cancer (Section 22.18), from the given compounds. You may use any other needed organic compounds or inorganic reagents.arrow_forwardSafrole, which is isolated from sassafras, can be converted to the illegal stimulant MDMA (3,4- methylenedioxymethamphetamine, “Ecstasy”) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.arrow_forward18.65 Propose a plausible synthesis for the following trans- formation. CH3 CH3 CH3arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY