Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 16.SE, Problem 41MP
In the Gatterman-Kochreaction, a formyl group (—CHO) is introduced directly onto a benzene ring. For example, reaction of toluene with CO and HCl in the presence of mixed CuCl/AlC3 gives p-methylbenzaldehyde. Propose a mechanism.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
H₂C
ཏཱཏི 1 ནི
OH
1. Br2, PBг3
2. H₂O
H3C
OH
Br
The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can
be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the
acid bromide completes the reaction.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
:0:
H3C
Br
Br
+
:::OH2
Br
H₂O
H3C
Br
за
Dihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesul-
fonic acid, ARSO,H. Propose a mechanism for this conversion.
ARSO,H
OH
+ H,O
Tetrahydrofurfuryl
Dihydropyran
alcohol
a) Reaction of 2-methyl propene with methanol in acid-catalyzed medium step by step showing the mechanism, show the product to be formed.
b) Starting from benzene, synthesize the following substances by choosing the appropriate reagents.
1) m-chloro benzoic acid
2) p-nitro phenol
Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Prob. 1PCh. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SŪ4. deuterium...Ch. 16.3 - Prob. 5PCh. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P
Ch. 16.4 - Prob. 11PCh. 16.4 - Acetanilide is less reactive than aniline toward...Ch. 16.4 - Prob. 13PCh. 16.5 - At what position would you expect electrophilic...Ch. 16.5 - Show the major product(s) from reaction of the...Ch. 16.6 - The herbicide oxyfluorfen can be prepared by...Ch. 16.7 - Treatment of p-bromotoluene with NaOH at 300°C...Ch. 16.8 - Prob. 18PCh. 16.8 - Prob. 19PCh. 16.8 - Prob. 20PCh. 16.9 - Prob. 21PCh. 16.10 - Prob. 22PCh. 16.10 - Prob. 23PCh. 16.SE - Prob. 24VCCh. 16.SE - The following molecular model of a...Ch. 16.SE - Prob. 26VCCh. 16.SE - Prob. 27VCCh. 16.SE - Aromatic iodination can be carried out with a...Ch. 16.SE - Prob. 29MPCh. 16.SE - The carbocation electrophile in a Friede1-Crafts...Ch. 16.SE - Prob. 31MPCh. 16.SE - The nitroso group, —N=O, is one of the few...Ch. 16.SE - Triphenylmethane can be prepared by reaction of...Ch. 16.SE - Using resonance structures of the intermediates,...Ch. 16.SE - Benzene and alkyl -substituted benzenes can be...Ch. 16.SE - Prob. 36MPCh. 16.SE - Hexachlorophene, a substance used in the...Ch. 16.SE - Benzenediazonium carboxylate decomposes when...Ch. 16.SE - 4-Chloropyridine undergoes reaction with...Ch. 16.SE - Propose a mechanism to account for the following...Ch. 16.SE - In the Gatterman-Kochreaction, a formyl group...Ch. 16.SE - Treatment of p-tert-butylphenol with a strong acid...Ch. 16.SE - Benzyl bromide is converted into benzaldehyde by...Ch. 16.SE - Prob. 44MPCh. 16.SE - Prob. 45MPCh. 16.SE - Prob. 46APCh. 16.SE - Prob. 47APCh. 16.SE - Prob. 48APCh. 16.SE - Predict the major monoalkylation products you...Ch. 16.SE - Name and draw the major product(s) of...Ch. 16.SE - Prob. 51APCh. 16.SE - Prob. 52APCh. 16.SE - What product(s) would you expect to obtain from...Ch. 16.SE - Prob. 54APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 56APCh. 16.SE - Prob. 57APCh. 16.SE - Prob. 58APCh. 16.SE - Prob. 59APCh. 16.SE - Prob. 60APCh. 16.SE - Prob. 61APCh. 16.SE - Prob. 62APCh. 16.SE - Prob. 63APCh. 16.SE - How would you synthesize the following substances...Ch. 16.SE - Prob. 65APCh. 16.SE - Prob. 66APCh. 16.SE - Draw resonance structures of the intermediate...Ch. 16.SE - Prob. 68APCh. 16.SE - p-Bromotoluene reacts with potassium amide to give...Ch. 16.SE - Prob. 70APCh. 16.SE - Prob. 71APCh. 16.SE - Prob. 72APCh. 16.SE - Use your knowledge of directing effects, along...Ch. 16.SE - Identify the reagents represented by the letters...Ch. 16.SE - Phenols (ArOH) are relatively acidic, and the...Ch. 16.SE - Prob. 76APCh. 16.SE - Prob. 77APCh. 16.SE - Melamine, used as a fire retardant and a component...
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
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardKnoevenagel condensation is a reaction involving an active methylene compound (a CH2 flanked by two electron-withdrawing groups) and an aldehyde and ketone. Propose a mechanism for the reaction below.arrow_forwardDihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesulfonic acid, ArSO3H. Propose a mechanism for this conversion.arrow_forward
- H3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br Brarrow_forwardThe following set of reactions convert phenylacetylene to butylbenzene. Give the appropriate reagents for each step of the following reaction sequence.arrow_forwardA vicinal diol has OH groups on adjacent carbons. The dehydration of a vicinal diol is accompanied by a rearrangement called the pinacol rearrangement. Propose a mechanism for this reaction.arrow_forward
- Provide the reagent(s) and the reaction mechanism of the following reaction H₂Narrow_forwardX6-156. Arrange the following substituted anilines in increasing order of reactivity toward acetic anhydride: sllo NH2 ร้อเป็น NH2 NH2 edi NH2 O₂N. (a) (b) ---- (c) (d) bund NO2 CI H3C-N-CH3 Insmiy X 6-157. Suggest a mechanism for the preparation of acetic anhydride from acetic acid and acetyl chloride in the presence pyridine (an amine base).arrow_forwardStep by step reaction of 2-methyl propene with methanol in acid-catalyzed medium showing the mechanism, show the product to be formedarrow_forward
- Under acid catalysis, tetrahydrofurfuryl alcohol reacts to give surprisingly good yields of dihydropyran. Propose a mechanism to explain this useful synthesis.arrow_forwardWhen diethyl ether (CH3CH2OCH2CH3) is treated with concentrated HBr, the initial products are CH3CH2Br and CH3CH2OH. Propose a mechanism to account for this reaction.arrow_forward5-Androstene-3,17-dione is isomerized to 4-androstene-3,17-dione by hydroxide ion. Propose a mechanism for this reactionarrow_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
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License