Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 21.SE, Problem 60AP
Interpretation Introduction
Interpretation:
The step-growth
Concept introduction:
This step growth
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Carototoxin is a natural pesticide produced by carrots, with formula C₁H2O. It undergoes hydrogenation with Pd to:
give product A, C,H,O, and with Lindlar's catalyst to give product B, C,H2O. Ozonolysis followed by zinc leads to a
mixture of methanal, octanal, 1,2-ethanedioic acid, 3-oxopropanoic acid, and 2-hydroxy-3-oxopropanoic acid. Draw
possible structures for carototoxin, A, and B.
Product B structure
H2, Lindlar's
Structure of
carototoxin
H2, Pd/C
Product A structure
CH,OCH,CI
SnCl,
CH,CI
The chloromethylated polystyrene resin used for Merrifield solid-phase peptide synthesis is prepared by treatment of polystyrene with chloromethylmethyl ether and a Lewis acid catalyst. The
reaction involves the following steps:
1. Reaction of the ether with the Lewis acid to form cation 1;
2. Electrophilic aromatic substitution to form resonance stzbilized cation 2:
3. Deprotonation yields aromatic ether 3:
4. Protonation to žorm protonated ether 4;
5. Displacement by chloride ion to form the final product
Write out the mechanism on a separate sheet of paper and then draw the structure of the resonance contributors of the resonance stabilized cation 2.
• Use Rl groups to indicate the points where the polymer repeats. The R group tool is located in the charges and lone pairs drop-down menu.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
• Separate resonance structures using the symbol from the…
Benzene can be hydroxylated by treating it with hydrogen peroxide and a strong acid such as trifluoromethanesulfonic acid (TfOH). Propose amechanism for this reaction
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
Similar questions
- Epoxy adhesives are prepared in two steps. SN2 reaction of the disodium salt of bisphenol A with epichlorohydrin forms a prepolymer, which is then cured by treatment with a triamine such as H2NCH2CH2NHCH2CH2NH2. Draw structures to show how addition of the triamine results in a strengthening of the polymer.arrow_forwardPolycarbonates (Section 29.5C) are also formed by using a nucleophilic aromatic substitution route (Section 22.3B) involving aromatic difluoro monomers and carbonate ion. Propose a mechanism for this reaction.arrow_forwardDraw a structural formula of the polymer resulting from base-catalyzed polymerization of each compound. Would you expect the polymers to be optically active? (S)-(+)-lactide is the dilactone formed from two molecules of (S)-(+)-lactic acid.arrow_forward
- Draw the structure of the products that will be formed when aniline reacts with nitrous acid at 5oC, followed by: (a) CuCN(b) CuBrarrow_forwardShow how the styrene can be prepared from benzene:arrow_forwardIsoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.arrow_forward
- Butanol is treated with H2SO4 and heat. Identify the reaction and give the product that can be formed from itarrow_forwardPolycarbophil is a dietary fiber supplement. It is the calcium salt of a copolymer of acrylic acid and divinyl glycol, a cross-linking agent. In the stomach, the calcium ions exchange for protons and, in the higher pH of the intestine, the polymer absorbs 70 times its mass in ОН OH Divinyl glycol water. (a) Propose a structure for polycarbophil. (b) Why is cross-linking of the polymer necessary for this application? (c) Why is polycarbophil effective at providing bulk in the intestine? That is, what occurs on a molecular level to polycarbophil?arrow_forwardQuinolines, heterocyclic compounds that contain a pyridine ring fused to a benzene ring, are commonly synthesized by a method known as the Skraupsynthesis, in which aniline reacts with glycerol under acidic conditions. Nitrobenzene is added to the reaction mixture to serve as an oxidizing agent.The first step in the synthesis is the dehydration of glycerol to propenal. a. What product would be obtained if para-ethylaniline were used instead of aniline?b. What product would be obtained if 3-hexen-2-one were used instead of glycerol?c. What starting materials are needed for the synthesis of 2,7-diethyl-3-methylquinoline?arrow_forward
- Structure of product C A hydrocarbon, A, with formula C11H16 undergoes hydrogenation with Pd to give product B, C11H22, and with Lindlar's catalyst to give product C, C11 H18. Ozonolysis leads to a mixture of products including cyclohexanone and 4-oxobutanoic acid. Treatment with sodium amide (NaNH2) followed by bromoethane gives compound D, C13H20. Draw possible structures for A, B, C, and D. H₂, Lindlar's Problem 13 of 14 Structure of A 1. NaNH2 Submit 2. CH3CH₂Br Structure of product Darrow_forwardAt one time, a raw material for the production of hexamethylenediamine was the pen- tose-based polysaccharides of agricultural wastes such as oat hulls. Treatment of these wastes with sulfuric acid or hydrochloric acid gives furfural. Decarbonylation of furfural over a zinc-chromium-molybdenum catalyst gives furan. Propose reagents and experi- mental conditions for the conversion of furan to hexamethylenediamine. Zn-Cr-Mo catalyst oat hulls, corn H,SO, cobs, sugar cane stalks H,0 CH Furfural Furan Tetrahydro- furan (THF) CI(CH,),CI N=C(CH2),C=N H,N(CH,),NH, 1,4-Dichloro- Hexanedinitrile 1,6-Hexanediamine butane (Adiponitrile) (Hexamethylenediamine)arrow_forwardSharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.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 LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole