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
Concept explainers
Question
Chapter 17, Problem 31P
Interpretation Introduction
Interpretation:
The relationship between two compounds that are formed by the oxidation of
Concept introduction:
The replacement or substitution of one
In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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.
Isoerythrogenic 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.
A certain compound of molecular formula C19H38 was isolated from fish oil and from plankton. On hydrogenation it gave 2,6,10,14-tetramethylpentadecane. Ozonolysis gave (CH3)2C O and a 16-carbon aldehyde. What is the structure of the natural product? What is the structure of the aldehyde?
Chapter 17 Solutions
Organic Chemistry - Standalone book
Ch. 17.1 - Prob. 1PCh. 17.2 - The heats of combustion of 1, 2-epoxybutane...Ch. 17.3 - Prob. 3PCh. 17.4 - Prob. 4PCh. 17.5 - Prob. 5PCh. 17.6 - Problem 17.6 (a) Write equations describing two...Ch. 17.6 - Problem 17.7 Only one combination of alkyl halide...Ch. 17.6 - Prob. 8PCh. 17.8 - Prob. 9PCh. 17.8 - Prob. 10P
Ch. 17.9 - Prob. 11PCh. 17.10 - Problem 17.12 Classify the bromohydrins formed...Ch. 17.11 - Prob. 13PCh. 17.11 - Prob. 14PCh. 17.12 - Prob. 15PCh. 17.12 - Prob. 16PCh. 17.14 - Prob. 17PCh. 17.15 - Prob. 18PCh. 17.16 - Prob. 19PCh. 17.17 - Problem 17.20 There is another oxygen-stabilized...Ch. 17 - Prob. 21PCh. 17 - Many ethers, including diethyl ether, are...Ch. 17 - Although epoxides are always considered to have...Ch. 17 - The name of the parent six-membered...Ch. 17 - Prob. 25PCh. 17 - Prob. 26PCh. 17 - Prob. 27PCh. 17 - Prob. 28PCh. 17 - Prob. 29PCh. 17 - Given that: does the product of the analogous...Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - Prob. 36PCh. 17 - When (R)-(+)-2-phenyl-2-butanol is allowed to...Ch. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Write a mechanism for the following reaction.Ch. 17 - Prob. 41PCh. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - Prob. 44PCh. 17 - Prob. 45PCh. 17 - Prob. 46DSPCh. 17 - Prob. 47DSPCh. 17 - Prob. 48DSPCh. 17 - Prob. 49DSPCh. 17 - Epoxide Rearrangements and the NIH Shift This...Ch. 17 - Epoxide Rearrangements and the NIH Shift This...
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
- Compound A and compound B both have molecular formula C6H12. Both compounds produce epoxides when treated with a peroxy acid (RCO3H). The epoxide resulting from compound A was treated with aqueous acid (H3O+) and the resulting diol has no chiral centers. Identify the two possible structures for compound A (enter two numbers separated by commas with no spaces, e.g. "1,2") The epoxide resulting from compound B was treated with (H3O*) and the resulting diol was a meso compound. Identify compound B 2 3 potn 7 1 5 6 4 8arrow_forwardStructure 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_forwardThe sex attractant of the housefly has the formula C23H46. When treated with warm potassium permanganate, this pheromone gives two products: CH3(CH2)12COOH and CH3(CH2)7COOH. Suggest a structure for this sex attractant. Explainwhich part of the structure is uncertainarrow_forward
- Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.arrow_forwardThree isomeric pentanols with unbranched carbon chains exist. Which of these isomers, upon dehydration at 180C, yields only 1-pentene as a product?arrow_forwardAccount for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.arrow_forward
- Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6- dimethyloctane when treated with H2 and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C = O, CH2 = O, CH2(CHO)2, and CH3COCHO. Ozonolysis of myrcene yields (CH3)2C = O, CH2 = O, (two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.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_forwardEast Indian sandalwood oil contains a hydrocarbon given the name santene (C9H14). Ozonolysis of santene gives the compound shown. What is the structure of santene?arrow_forward
- 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 structurearrow_forwardAn unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C)of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C, and E.arrow_forwardCompound 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_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
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,