Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 8.SE, Problem 37MP
Dichlorocarbene can be generated by heating sodium trichloroacetate. Propose a mechanism for the reaction, and use curved arrows to indicate the movement of electrons in each step. What relationship does your mechanism bear to the base-induced elimination of HC1 from chloroform?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
o - Nitroaniline is more soluble in ethanol than p - nitroaniline. Propose a scheme by which a pure sample of o-nitroaniline might be obtained from this reaction
What are the three alkenes formed in the acid-catalyzed dehydration of 2-pentanol? Propose the mechanism of their formation.
Propose a mechanism for the acid-catalyzed hydration of methylidenecyclohexane to give 1-methylcyclohexanol. Which step in your mechanism is rate-determining?
Chapter 8 Solutions
Organic Chemistry
Ch. 8.1 - Prob. 1PCh. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3PCh. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5PCh. 8.3 - Prob. 6PCh. 8.4 - Prob. 7PCh. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9PCh. 8.5 - What alkenes might be used to prepare the...
Ch. 8.5 - Tho following cycloalkene gives a mixture of two...Ch. 8.6 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.7 - Starting with an alkene, how would you prepare...Ch. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - What products would you expect from the following...Ch. 8.10 - Prob. 18PCh. 8.10 - Prob. 19PCh. 8.13 - Prob. 20PCh. 8.13 - What products are formed from hydration of...Ch. 8.SE - Name the following alkenes, and predict the...Ch. 8.SE - Prob. 23VCCh. 8.SE - Prob. 24VCCh. 8.SE - Prob. 25VCCh. 8.SE - Prob. 26MPCh. 8.SE - Prob. 27MPCh. 8.SE - Draw the structures of the organoboranes formed...Ch. 8.SE - Prob. 29MPCh. 8.SE - Provide the mechanism and products for the...Ch. 8.SE - Propose a curved-arrow mechanism to show how ozone...Ch. 8.SE - Prob. 32MPCh. 8.SE - Prob. 33MPCh. 8.SE - Prob. 34MPCh. 8.SE - 10-Bromo- α -chamigrene, a compound isolated from...Ch. 8.SE - Isolated from marine algae, prelaureatin is...Ch. 8.SE - Dichlorocarbene can be generated by heating sodium...Ch. 8.SE - Reaction of cyclohexene with mercury(II) acetate...Ch. 8.SE - Use your general knowledge of alkene chemistry to...Ch. 8.SE - Prob. 40MPCh. 8.SE - Hydroboration of 2-methyl-2-pentene at 25°C,...Ch. 8.SE - Prob. 42APCh. 8.SE - Suggest structures for alkenes that give the...Ch. 8.SE - Prob. 44APCh. 8.SE - Prob. 45APCh. 8.SE - Prob. 46APCh. 8.SE - Prob. 47APCh. 8.SE - Predict the products of the following reactions....Ch. 8.SE - Prob. 49APCh. 8.SE - How would you carry out the following...Ch. 8.SE - Draw the structure of an alkene that yields only...Ch. 8.SE - Show the structures of alkenes that give the...Ch. 8.SE - Prob. 53APCh. 8.SE - Which of the following alcohols could not be made...Ch. 8.SE - Prob. 55APCh. 8.SE - Prob. 56APCh. 8.SE - Prob. 57APCh. 8.SE - Compound A has the formula C10HI6. On catalytic...Ch. 8.SE - Prob. 59APCh. 8.SE - Prob. 60APCh. 8.SE - Prob. 61APCh. 8.SE - Draw the structure of a hydrocarbon that absorbs 2...Ch. 8.SE - Prob. 63APCh. 8.SE - The sex attractant of the common housefly is a...Ch. 8.SE - Prob. 65APCh. 8.SE - Prob. 66APCh. 8.SE - α-Terpinene, C10H16, is a pleasant-smelling...Ch. 8.SE - Prob. 68APCh. 8.SE - Prob. 69APCh. 8.SE - Prob. 70APCh. 8.SE - Prob. 71APCh. 8.SE - Prob. 72AP
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
- Following is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.arrow_forwardFollowing is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.arrow_forwardUsing your reaction roadmaps as a guide, show how to convert (2-methylpropyl) benzene into 4-phenyl-3-buten-2-one. You must use (2-methylpropyl) benzene as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.arrow_forward
- Using your reaction roadmap as a guide, show how to convert 3-hexyne into propanal. All of the carbon atoms of the target molecule must be derived from the starting material as efficiently as possible. Show all intermediate molecules synthesized along the way.arrow_forwardThe base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.arrow_forwardPropose a mechanism for the acid-catalyzed hydration of 1-methylcyclohexene to give 1-methylcyclohexanol. Which step in your mechanism is rate-determining?arrow_forward
- Propose a mechanism for the acid-catalyzed hydration of 3-methyl-1-butene to give 2-methyl-2-butanolarrow_forward(a) Arrange the following compounds in an increasing order of their indicated property :(i) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(ii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH,(CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)(b) How would you bring about the following conversions :(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde(iii) Bromobenzene to 1-phenylethanolarrow_forwardGive the shortest route to produce the desired products 1. cyclobutanoic acid to ethyl-cyclobutyl ketone 2. 2-butanone to pentatonic acid 3. propane to butanaminearrow_forward
- Predict the major products of dehydration catalyzed by sulfuric acid. (a) cyclopentylmethanol (b) 2-methylcyclopentanolarrow_forwardThe pyrolysis of acetic esters to give an alkene and acetic acid is thought to involve a planar transition state and cyclic redistribution of (4n + 2) electrons. Propose a mechanism for pyrolysis of the following ester.arrow_forwardUsing your reaction roadmaps as a guide, show how to convert 4-methyl-1-pentene and carbon dioxide into 5-methylhexanoic acid. You must use 4-methyl-1-pentene and carbon dioxide as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.arrow_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
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY