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 21.5, Problem 15P
What product would you expect from reaction of one equivalent of methanol with a cyclic anhydride, such as phthalic anhydride (1,2-benzenedicarboxylic anhydride)? What is the fate of the second “half” of the anhydride?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
What product would you obtain by reduction of benzaldehyde?
Unlike a phosphonium ylide that reacts with an aldehyde or a ketone to form an alkene, a sulfonium ylide reacts with an aldehyde or a ketone to form anepoxide. Explain why one ylide forms an alkene, whereas the other forms an epoxide.
Define what is reduction reaction, reducing agents, weak and strong reducing agents
sodium borohydride reduction with benzophenone and sodium borohyride to get benzophenone
Chapter 21 Solutions
Organic Chemistry
Ch. 21.1 - Give IUPAC names for the following substances:Ch. 21.1 - Draw structures corresponding to the following...Ch. 21.2 - Prob. 3PCh. 21.2 - Rank the compounds in each of the following sets...Ch. 21.2 - Predict the products of the following nucleophilic...Ch. 21.2 - Prob. 6PCh. 21.3 - Prob. 7PCh. 21.3 - If the following molecule is treated with acid...Ch. 21.4 - How might you prepare the following esters using a...Ch. 21.4 - Prob. 10P
Ch. 21.4 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - What product would you expect from reaction of one...Ch. 21.6 - Prob. 16PCh. 21.6 - Prob. 17PCh. 21.6 - Show the products you would obtain by reduction of...Ch. 21.6 - What ester and what Grignard reagent might you...Ch. 21.7 - Prob. 20PCh. 21.7 - How would you use the reaction of an amide with...Ch. 21.8 - Write the mechanism of the reaction shown in...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.10 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.SE - Name the following compounds:Ch. 21.SE - Prob. 28VCCh. 21.SE - Prob. 29VCCh. 21.SE - Prob. 30VCCh. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the complete...Ch. 21.SE - Prob. 35MPCh. 21.SE - When 4-dimethylaminopyridine (DMAP) is added in...Ch. 21.SE - Prob. 37MPCh. 21.SE - Prob. 38MPCh. 21.SE - Prob. 39MPCh. 21.SE - The hydrolysis of a biological thioester to the...Ch. 21.SE - Prob. 41MPCh. 21.SE - Prob. 42MPCh. 21.SE - Prob. 43MPCh. 21.SE - In the iodoform reaction, a triiodomethyl ketone...Ch. 21.SE - Give IUPAC names for the following compounds:Ch. 21.SE - Prob. 46APCh. 21.SE - Draw and name compounds that meet the following...Ch. 21.SE - Predict the product, if any, of reaction between...Ch. 21.SE - Prob. 49APCh. 21.SE - Prob. 50APCh. 21.SE - What product would you expect to obtain from...Ch. 21.SE - Prob. 52APCh. 21.SE - Prob. 53APCh. 21.SE - The following reactivity order has been found for...Ch. 21.SE - Prob. 55APCh. 21.SE - Outline methods for the preparation of...Ch. 21.SE - Prob. 57APCh. 21.SE - When ethyl benzoate is heated in methanol...Ch. 21.SE - tert-Butoxycarbonyl azide, a reagent used in...Ch. 21.SE - Prob. 60APCh. 21.SE - Prob. 61APCh. 21.SE - What is the structure of the polymer produced by...Ch. 21.SE - Polyimides with the structure shown are used as...Ch. 21.SE - Prob. 64APCh. 21.SE - Propose a structure for a compound, C4H7ClO2, that...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Prob. 67APCh. 21.SE - When a carboxylic acid is dissolved in...Ch. 21.SE - Prob. 69APCh. 21.SE - Prob. 70APCh. 21.SE - Prob. 71APCh. 21.SE - Phenyl 4-aminosalicylate is a drug used in the...Ch. 21.SE - N,N-Diethyl-m-toluamide (DEET) is the active...Ch. 21.SE - Tranexamic acid, a drug useful against blood...Ch. 21.SE - One frequently used method for preparing methyl...Ch. 21.SE - Prob. 76APCh. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Propose structures for compounds with the...Ch. 21.SE - Propose a structure for the compound with the...Ch. 21.SE - Draw the structure of the compound that produced...Ch. 21.SE - Prob. 81APCh. 21.SE - Epoxy adhesives are prepared in two steps. SN2...
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
- Unlike a phosphonium ylide that reacts with an aldehyde or a ketone to form an alkene, a sulfonium ylide reacts with an aldehyde or a ketone to form an epoxide. Explain why one ylide forms an alkene, whereas the other forms an epoxide.arrow_forwardWhat products would you would expect to obtain when the following compounds react with ozone and then with dimethylsulfide?arrow_forwardWrite the structure of the principal organic product obtained on nitration of each of the following: (a) p-Methylbenzoic acid (d) p-Methoxyacetophenone (b) m-Dichlorobenzene (e) p-Methylanisole (c) m-Dinitrobenzene (f ) 2,6-Dibromoanisolearrow_forward
- Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide.What is the leaving group in your proposed mechanism? Would this be a suitableleaving group for an SN2 reaction?arrow_forwardNucleophilic aromatic substitution provides one of the common methods for making phenols. ) Show how you would synthesize the following phenols, using benzene or toluene as your aromatic starting material, and explain why mixtures of products would be obtained in some cases. (a) m-cresol (b) p-n-butylphenolarrow_forward(a) How will you obtain the following :(i) Benzaldehyde from Phenol (ii) Benzoic acid from Aniline(b) Give reasons :(i) Aldehydes are more reactive than ketones towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give the characteristic reactions of carbonyl group.arrow_forward
- What is the product resulted due to the reaction of 2-hydroxy-3-methoxybenzaldehyde with ethyl bromoacetate in a basic solution indicating all the reagents and intermediates occurred during the reaction?arrow_forwardWhat is the major product(s) of each of the following reactions? a. bromination of p-methylbenzoic acid b. chlorination of o-benzenedicarboxylic acid c. bromination of p-chlorobenzoic acid d. nitration of p-fluoroanisole e. nitration of p-methoxybenzaldehyde f. nitration of p-tert-butylmethylbenzenearrow_forwardThe following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.arrow_forward
- 1. The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents. 2. Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.arrow_forwardWhat condensation product would you expect to obtain by treatment of the following substances with sodium ethoxide in ethanol. Cycloheptanonearrow_forward2,6-Dimethoxybenzoic acid was needed for a synthesis of the β-lactam antibiotic methicillin. Show how this carboxylic acid could be synthesized from 2-bromo-1,3-benzenediol.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
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