Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 8, Problem 8.68SP
Interpretation Introduction
Interpretation: The structure of the unknown compound is to be predicted.
Concept introduction: Halohydration of
To determine: The structure of the unknown compound.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
An unknown hydrocarbon decolorizes bromine in CCl4CCl4, and it undergoes catalytic reduction to give cis-decalin. When treated with warm, concentrated potassium permanganate, this compound gives cis-1,2-cyclohexanedicarboxylic acid. Propose a structure for the unknown compound.
Compound A of molecular formula C8H₁4 is reduced by sodium in liquid ammonia to give compound
of molecular formula C8H16. product (Y).
Both A and B undergo hydrogenation in the presence of a platinum catalyst to give 2,5-
dimethylhexane. Ozonolysis of B with an oxidative workup produces a carboxylic acid of molecular
formula C4H8O2. Reaction of B with a peroxyacid gives a chiral C8H₁40 product, but reaction with
bromine gives an achiral C8H₁4Br2 product. What are the identities of A and B?
14
A is 2,5-dimethyl-3-hexyne; B is cis-2,5-dimethyl-3-hexene
A is 2,5-dimethyl-3-hexyne; B is trans-2,5-dimethyl-3-hexene
A is 2,5-dimethyl-1,5-hexadiene; B is 2,5-dimethyl-3-hexyne
A is 2,5-dimethyl-2,4-hexadiene; B is cis-2,5-dimethyl-3-hexene
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 D
Chapter 8 Solutions
Organic Chemistry (9th Edition)
Ch. 8.3A - Predict the major products of the following...Ch. 8.3A - a. When 1 mole of buta-1,3-diene reacts with 1...Ch. 8.3B - Predict the major products of the following...Ch. 8.3B - Show how you would accomplish the following...Ch. 8.4B - Propose a mechanism to show how...Ch. 8.4B - Predict the products of the following hydration...Ch. 8.6 - a. Propose a mochansm fortho following reaction....Ch. 8.6 - Prob. 8.8PCh. 8.6 - Prob. 8.9PCh. 8.7A - Prob. 8.10P
Ch. 8.7A - Prob. 8.11PCh. 8.7C - Prob. 8.12PCh. 8.7C - Prob. 8.13PCh. 8.7C - a. When (Z)-3-methylhex-3-ene undergoes...Ch. 8.7C - Prob. 8.15PCh. 8.7C - Prob. 8.16PCh. 8.8B - Prob. 8.17PCh. 8.8B - Prob. 8.18PCh. 8.9 - Prob. 8.19PCh. 8.9 - Prob. 8.20PCh. 8.9 - Prob. 8.21PCh. 8.9 - Prob. 8.22PCh. 8.10 - Prob. 8.23PCh. 8.10 - Prob. 8.24PCh. 8.10 - Prob. 8.25PCh. 8.11A - Prob. 8.26PCh. 8.11B - Prob. 8.27PCh. 8.11B - Prob. 8.28PCh. 8.12 - Prob. 8.29PCh. 8.13 - a. Propose a mechanism for the conversion of...Ch. 8.13 - Magnesium monoperoxyphthalate (MMPP) epoxidizes...Ch. 8.13 - Predict the major products of the following...Ch. 8.13 - When 1,2-epoxycyclohexane (cyclohexene oxide) is...Ch. 8.14C - Predict the major products of the following...Ch. 8.14C - Prob. 8.35PCh. 8.15B - Prob. 8.36PCh. 8.15C - Predict the major products of the following...Ch. 8.16A - Prob. 8.38PCh. 8.16A - Prob. 8.39PCh. 8.16B - Prob. 8.40PCh. 8.16B - Prob. 8.41PCh. 8.16C - Prob. 8.42PCh. 8.17B - Prob. 8.43PCh. 8.17B - Prob. 8.44PCh. 8.17B - Show how you would synthesize each compound,...Ch. 8 - Prob. 8.46SPCh. 8 - Prob. 8.47SPCh. 8 - Give the products expected when the following...Ch. 8 - Show how you would make the following compounds...Ch. 8 - Using 1,2-dimethylcyclohexene as your starting...Ch. 8 - Show how you would synthesize each compound using...Ch. 8 - Prob. 8.52SPCh. 8 - Show how you might use olefin metathesis to...Ch. 8 - Prob. 8.54SPCh. 8 - Prob. 8.55SPCh. 8 - Propose mechanisms consistent with the following...Ch. 8 - Prob. 8.57SPCh. 8 - Prob. 8.58SPCh. 8 - Draw a reaction-energy diagram for the propagation...Ch. 8 - Prob. 8.60SPCh. 8 - Prob. 8.61SPCh. 8 - Prob. 8.62SPCh. 8 - Prob. 8.63SPCh. 8 - Prob. 8.64SPCh. 8 - Prob. 8.65SPCh. 8 - Prob. 8.66SPCh. 8 - Prob. 8.67SPCh. 8 - Prob. 8.68SPCh. 8 - Prob. 8.69SPCh. 8 - Prob. 8.70SPCh. 8 - Prob. 8.71SPCh. 8 - Prob. 8.72SPCh. 8 - Prob. 8.73SPCh. 8 - Prob. 8.74SPCh. 8 - Prob. 8.75SPCh. 8 - Prob. 8.76SPCh. 8 - Prob. 8.77SPCh. 8 - Prob. 8.78SPCh. 8 - Prob. 8.79SP
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 of molecular formula C8H14 is reduced by sodium in liquid ammonia to give compound B of molecular formula C8H16. product (Y).Both A and B undergo hydrogenation in the presence of a platinum catalyst to give 2,5-dimethylhexane. Ozonolysis of B with an oxidative workup produces a carboxylic acid of molecular formula C4H8O2. Reaction of B with a peroxyacid gives a chiral C8H14O product, but reaction with bromine gives an achiral C8H14Br2 product. What are the identities of A and B?arrow_forwardMyristoleic acid, C14H26O2, yields myristic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield pentanoic acid and nonanedioic acid. Draw the structure of Myristoleic acid.arrow_forwardCarototoxin 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_forward
- Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.arrow_forward1-Phenyl-2-butanol is used in perfumery. Show how to synthesize this alcohol from bromobenzene, 1-butene, and any necessary inorganic reagents.arrow_forwardFollowing is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forward
- 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.arrow_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_forwardIsoprene 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.arrow_forward
- Triphenylmethanol is insoluble in water, but when it is treated with concentrated sulfuric acid, a bright yellow solution results. As this yellow solution is diluted with water, its color disappears and a precipitate of triphenylmethanol reappears. Suggest a structure for the bright yellow species, and explain this unusual behavior.arrow_forwardAn optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.arrow_forwardWolff–Kishner reduction (hydrazine, KOH, ethylene glycol, 130°C) of the compound shown gave compound A. Treatment of compound A with m-chloroperoxybenzoic acid (MCPBA) gave compound B, which on reduction with lithium aluminum hydride gave compound C. Oxidation of compound C with chromic acid gave compound D (C9H14O). Identify compounds A through D in this sequence.arrow_forward
arrow_back_ios
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
How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY