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
Question
Chapter 12, Problem 62P
Interpretation Introduction
Interpretation:
The structure of compound niacin having the molecular formula
Concept introduction:
Chromic acid and potassium permanganate are oxidizing agents. They oxidize alkyl benzenes which have at least one benzylic hydrogen. Benzylic hydrogens are those which are attached to the benzylic carbon atoms.
The benzene ring itself is not oxidized; only side chains are oxidized to produce benzoic acid.
If a substituent attached to the benzene ring does not have any benzylic hydrogens, it remains as it in the presence of chromic acid. It is not oxidized.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Trimyristin is obtained from coconut oil and has the molecular formula C45H86O6. On being heated with aqueous sodium hydroxide followed by acidification, trimyristin was converted to glycerol and tetradecanoic acid as the only products. What is the structure of trimyristin?
Isoprene has sometimes been used as a starting material in the laboratory synthesis of terpenes. In one such synthesis, the first step is the electrophilic addition of 2 mol of hydrogen bromide to isoprene to give 1,3-dibromo-3-methylbutane.Write a series of equations describing the mechanism of this reaction.
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
Chapter 12 Solutions
Organic Chemistry - Standalone book
Ch. 12.2 - Write structural formulas for toluene (C6H5CH3)...Ch. 12.3 - Prob. 2PCh. 12.5 - Prob. 3PCh. 12.5 - Prob. 4PCh. 12.6 - Prob. 5PCh. 12.6 - Chrysene is an aromatic hydrocarbon found in coal...Ch. 12.8 - Prob. 7PCh. 12.9 - As measured by their first-order rate constants,...Ch. 12.9 - Give the structure of the principal organic...Ch. 12.9 - Prob. 10P
Ch. 12.10 - Prob. 11PCh. 12.11 - Prob. 12PCh. 12.12 - Prob. 13PCh. 12.13 - Prob. 14PCh. 12.13 - Prob. 15PCh. 12.15 - The regioselectivity of Birch reduction of...Ch. 12.16 - Prob. 17PCh. 12.17 - Both cyclooctatetraene and styrene have the...Ch. 12.17 - Prob. 19PCh. 12.18 - Give an explanation for each of the following...Ch. 12.19 - Prob. 21PCh. 12.19 - What does a comparison of the heats of combustion...Ch. 12.20 - Prob. 23PCh. 12.20 - Prob. 24PCh. 12.20 - Prob. 25PCh. 12.20 - Prob. 26PCh. 12.20 - Prob. 27PCh. 12.20 - Prob. 28PCh. 12.21 - Prob. 29PCh. 12.21 - Prob. 30PCh. 12.22 - Prob. 31PCh. 12.22 - Prob. 32PCh. 12 - Write structural formulas and give the IUPAC names...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - Acridine is a heterocyclic aromatic compound...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - Evaluate each of the following processes applied...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Prob. 46PCh. 12 - Anthracene undergoes a DielsAlder reaction with...Ch. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - The relative rates of reaction of ethane, toluene,...Ch. 12 - Both 1,2-dihydronaphthalene and...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - Prob. 54PCh. 12 - Prob. 55PCh. 12 - Prob. 56PCh. 12 - Each of the following reactions has been described...Ch. 12 - Prob. 58PCh. 12 - A compound was obtained from a natural product and...Ch. 12 - Prob. 60PCh. 12 - Suggest reagents suitable for carrying out each of...Ch. 12 - Prob. 62PCh. 12 - Prob. 63DSPCh. 12 - Prob. 64DSPCh. 12 - Prob. 65DSPCh. 12 - Prob. 66DSP
Knowledge Booster
Similar questions
- Using Friedel Crafts alkylation of benzene, a group of scientists discovered compound A, C3H3O, an optically inactive compound. They discovered that compound B, CsH;BrO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C3H,B1NO3, is formed. While Friedel Crafts alkylation of compound A produces compound D. This compound D was oxidised to produce compound E, C9H§O3 as a major product. Compound F, C10H1002, was produced by Friedel Crafts acylation of compound A. This compound F reacts positively with alkaline iodine and 2,4- dinitrophenylhydrazine. However, it returns negative results for Tollens' and Benedict's tests. Identify the possible structural formulae compounds A to F and explain your answers.arrow_forwardCompound T (C6H6O) reacts with sodium hydroxide to form Compound U. Compound V can be formed when Compound T reacted with sodium. Compound W formed when Compound T reacts with dilute nitric acid at room temperature while Compound X formed when Compound T reacts with concentrated nitric acid at room temperature. Compound T reacts with Br2 in CS2 to produce Compound Y. Identify the possible structural formulae for compound T to Y and give TWO (2) characteristics of compound T.arrow_forwardSulphuric acid catalyzes the reaction between compound D and compound E producing propl hexanoate. This reaction is an example of Fischer esterification. Compound D reacts with phosphorus tribromide to give alkyl bromide. Draw the structure and give the name of compound D and Earrow_forward
- An unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a palladium catalyst to give B C6H12 (Rxn 1). Hydrocarbon A also reacts with OsO4 to give the glycol C (Rxn 2). A gives 5-oxohexanal on ozonolysis (Rxn 3). Draw the structures of A, B, and C. Give the reactions.arrow_forward1. Aromatic compounds are metabolized via transformation of the aromatic ring to a reactive metabolite, arene oxide. Suggest two possible reactions of this metabolite and provide the products of those reactions ? P450 aromatic arene ? compound oxide ?arrow_forwardCompound AA has a molecular formula of C3H6O and gives a positiveresult using Tollen’s reagent. The reaction of compound AA with hotacidified potassium permanganate, KMnO4 gives compound BB. Thecatalytic hydrogenation of compound AA with nickel, Ni producedcompound CC. The reaction of compound BB with ethanamine,CH3CH2NH2 produces compound DD I) Draw the structural formula of compounds AA, BB, CC and DD. 2)Name the type of chemical reaction for the formation of compound CC.arrow_forward
- One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forwardTreatment of pentanedioic (glutaric) anhydride with ammonia at elevated temperature leads to a compound of molecular formula C5H7NO2. What is the structure of this product? [Hint: You need to think about the reactivity not only of acid anhydrides but also of amides and carboxylic acids]arrow_forwardThere is a tick and mosquito repellent DEET (diethyltoluamide) that is prepared by a reaction of diethylamine with m-methylbenzomic acid (m-toluic acid) H+ and heat. What's the structure of DEET?arrow_forward
- Consider the compound C5H9Br (Compound X). It reacts with potassium tert-butoxide to give Compound Y, C5H8. Compound Y upon reaction with hydrogen produced methylcyclobutane. Compound Y upon reaction with ozone produces one compound with two aldehyde functional groups. Provide the structures of Compound X and Y.arrow_forwardAn aromatic compound K, whose molecular formula is C8H11N, is examined in the laboratory to elucidate its structure. The following observations were made: A) Compound K is soluble in dilute hydrochloric acid but insoluble in sodium hydroxide solution. B) Treatment of compound K with excess potassium hydroxide and benzenesulfonyl chloride, C(6)H(5)SO(2)Cl, results in the formation of a heterogeneous mixture. The NMR spectrum of compound K is shown below. C) Compound K when treated with acetic anhydride[CH3-C(O)-O-C(O)-CH3], gives compound L, whose molecular formula is C(10)H(13)ON. Compound L is insoluble in dilute acid or dilute base at room temperature, heating compound L in dilute acid or base, however, regenerates compound K. D) When compound L is heated with a mixture of concentrated nitric acid and sulfuric acid, a single product, compound M, with the molecular formula C(10)H(12)O(3)N(2) is formed in excellent yields. On the basis of these observations draw the structures of…arrow_forwardWhat happens when the codeine molecule (C18H21NO3) is exposed to air? What reactions are obtained?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
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning