ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 27.SE, Problem 48AP
α-Fenchone is a pleasant-smelling terpenoid isolated from oil of lavender. Propose a pathway for the formation of α-fenchone from geranyl diphosphate. A carbocation rearrangement is required.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Reaction of hbr with 2-methylpropene yields 2 bromo 2 methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of reaction.
Amantadine is effective in preventing infections caused by the influenza A virus and in
treating established illnesses. It is thought to block a late stage in the assembly of the
virus. Amantadine is synthesized by treating 1-bromoadamantane with acetonitrile in
sulfuric acid to give N-adamantylacetamide, which is then converted to amantadine.
CH,C=N
in H,SO,
Br
NHCCH3
NH2
1-Bromoadamantane
Amantadine
(a) Propose a mechanism for the transformation in Step 1.
(b) Describe experimental conditions to bring about Step 2.
Draw the major product of the reaction between 1-butanol and Na2Cr207, H2SO4, H2O.
O, O, e
CH
Chapter 27 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
Additional Science Textbook Solutions
Find more solutions based on key concepts
Q2. Which statement best defines chemistry?
a. The science that studies solvents, drugs, and insecticides
b. Th...
Introductory Chemistry (6th Edition)
The smallest building blocks inside your cell phone are about 1000 times smaller than the diameter of a human h...
Chemistry In Context
Problem 11.1 Neopheliosyne B is a novel acetylenic fatty acid isolated from a New Caledonian marine sponge. (a)...
Organic Chemistry
Characterize each of the following structures as aromatic, nonaromatic, or antiaromatic:
Answer: _____
Organic Chemistry As a Second Language: Second Semester Topics
How could you separate a mixture of the following compounds? The reagents available to you are water, either, 1...
Organic Chemistry
covered a synthesis of alkynes by a double dehydrohalogenation of dihalides. A student tried to convert trans-2...
Organic Chemistry (9th Edition)
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
- Propose a synthesis for (Z)-9-tricosene (muscalure), the sex pheromone for the common housefly (Musca domestica), starting with acetylene and haloalkanes as sources of carbon atoms.arrow_forwardThe addition of dilute H2SO4 in the presence of H9SO4 to 1-butyne produces an alcohol O an enol an enol followed by a ketone O an enol followed by a aldehydearrow_forward$ 2,6-Di-tert-butyl-4-methylphenol, alternatively known as butylated hydroxytoluene (BHT), is used as an antioxidant in foods to"retard spoilage" ( synthesized industrially from 4-methylphenol by reaction with 2-methylpropene in the presence of phosphoric acid. Propose a mechanism for this reaction. ВНT is OH OH H&PO, 4-Methylphenol 2-Methylpropene (p-Cresol) 2,6-Di-tert-butyl-4-methylphenol "Butylated hydroxytoluene" (BHT)arrow_forward
- Which of the following reagents would be used to convert 1-pentene to 1, 2- dibromopentane? O Br2/H20 O H2/Pt O Br2 HBr, ROOR O HBrarrow_forwardReaction with which of the following compounds in an acetylide reaction would lengthen the carbon chain by one carbon and add a primary alcohol? O ethanal O formaldehyde О ерохide O acetone O carbonic acid QUESTION 4 The reagent/reaction of choice for this reduction is || HC-CH=CH-CH2CH2CH2 CO2H CH2OH-CH=CH-CH2CH2CH2 CO2H O lithium aluminum hydride O potassium permanganate O sodium borohydride O Grignard reaction O SN2 reactionarrow_forwardTreatment of 3-chloro-2-cyclohexenone with sodium ethoxide in methanol gives 3-ethoxy-2-cyclohexene. Propose a mechanism for this reaction that accounts for the formation of the product.arrow_forward
- Using only 1-bromobutane as a carbon source in your reactions, propose a synthesis of 4-methyl-hexan-3-ol. The reaction mechanism is not required.arrow_forwardH₂C ཏཱཏི 1 ནི OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: H3C Br Br + :::OH2 Br H₂O H3C Br заarrow_forward9) How would you carry out the following transformation? More than one step may be required, write the reactions. H3C CH 3 H3C ? H3C CH3 OH H H3C H "ОН 10) How would you synthesize the following compound from cyclohexanone? More than one step may be required, write the reactions. CH 3arrow_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
Lipids - Fatty Acids, Triglycerides, Phospholipids, Terpenes, Waxes, Eicosanoids; Author: The Organic Chemistry Tutor;https://www.youtube.com/watch?v=7dmoH5dAvpY;License: Standard YouTube License, CC-BY