ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
expand_more
expand_more
format_list_bulleted
Question
Chapter 18.SE, Problem 64GP
Interpretation Introduction
Interpretation:
Starting from compounds having ten or fewer carbons how to synthesize racemic disparlure is to be shown.
Concept introduction:
Lower
To show:
Starting from compounds having ten or fewer carbons how to synthesize racemic disparlure.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
CCH
H20, H2SO4
H9SO4
CH3
Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov
regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called
an enol. The enol immediately rearranges to a more stable ketone via tautomerization.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Hjö:
-CH3
-CH3
H3O*
The following Wittig reactions may produce a mixture of alkene stereoisomers. Write the
products for each of the reactions and indicate the stereoisomers if any.
||
Ph,P
CH3
+
?
(1)
LOME
(2)
R
N.
Ph,P=CH,R'
Me
Draw a structural formula for the product formed upon hydroboration/oxidation of the alkene below.
CH3
OG
1
Use wedge and hash bonds ONLY for rings.
Do not show stereochemistry in other cases.
• If the reaction produces a racemic mixture, just draw one stereoisomer.
●
981
CH3
*****
//
Q
Y
?
[F
B
Chapter 18 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6PCh. 18.3 - Prob. 7PCh. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...
Ch. 18.5 - Prob. 11PCh. 18.6 - Predict the major product of each of the following...Ch. 18.6 - Prob. 13PCh. 18.6 - Predict the major product of the following...Ch. 18.7 - 15-Crown-5 and 12-crown-4 ethers complex Na+ and...Ch. 18.8 - Prob. 16PCh. 18.8 - 2-Butene-l-thiol is one component of skunk spray....Ch. 18.9 - The 1H NMR spectrum shown is that of a cyclic...Ch. 18.SE - Give IUPAC names for the following compounds...Ch. 18.SE - Show the product, including stereochemistry, that...Ch. 18.SE - Prob. 21VCCh. 18.SE - Treatment of the following alkene with a...Ch. 18.SE - Prob. 23MPCh. 18.SE - Prob. 24MPCh. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - The alkoxymercuration of alkenes involves the...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Prob. 29MPCh. 18.SE - Ethers undergo an acid-catalyzed cleavage reaction...Ch. 18.SE - Treatment of 1, 1-diphenyl-l, 2-epoxyethane with...Ch. 18.SE - Fluoxetine, a heavily prescribed antidepressant...Ch. 18.SE - When 2-methyl-2, 5-pentanediol is treated with...Ch. 18.SE - Prob. 34MPCh. 18.SE - Prob. 35MPCh. 18.SE - Aldehydes and ketones undergo acid-catalyzed...Ch. 18.SE - Propose a mechanism to account for the following...Ch. 18.SE - Prob. 38APCh. 18.SE - Prob. 39APCh. 18.SE - How would you prepare the following ethers?Ch. 18.SE - Prob. 41APCh. 18.SE - tert-Butyl ethers can be prepared by the reaction...Ch. 18.SE - Treatment of trans-2-chlorocyclohexanol with NaOH...Ch. 18.SE - Predict the products of the following ether...Ch. 18.SE - Prob. 45APCh. 18.SE - Prob. 46APCh. 18.SE - Write the mechanism of the hydrolysis of cis-5,...Ch. 18.SE - Prob. 48APCh. 18.SE - Acid-catalyzed hydrolysis of a 1,...Ch. 18.SE - Prob. 50APCh. 18.SE - Epoxides are reduced by treatment with lithium...Ch. 18.SE - Prob. 52APCh. 18.SE - The red fox (Vulpes vulpes) uses a chemical...Ch. 18.SE - Anethole, C10H12O, a major constituent of the oil...Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 56GPCh. 18.SE - How would you synthesize anethole (Problem 18-54)...Ch. 18.SE - How could you prepare benzyl phenyl ether from...Ch. 18.SE - Meerwein's reagent, triethyloxonium...Ch. 18.SE - Prob. 60GPCh. 18.SE - Prob. 61GPCh. 18.SE - The Zeisel method is an old analytical procedure...Ch. 18.SE - Prob. 63GPCh. 18.SE - Prob. 64GPCh. 18.SE - Prob. 65GPCh. 18.SE - Identify the reagents a-e in the following scheme:Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 68GPCh. 18.SE - Prob. 69GPCh. 18.SE - Predict the product(s) if the starting materials...
Knowledge Booster
Similar questions
- Draw the structural formula of the product of the reaction shown below. + H₂O AAVIL H₂SO4 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, just draw one stereoisomer. Sn [F Ⓡ ChemDoodlearrow_forwardhow can I synthesize 2,3,4-trimethylcyclopentadiene starting from a benzene ring or an organic compond with 3 carbons or less?arrow_forwardAUA34 04 H2 / Lindlar catalyst H30* /HgSO4 The polycyclic aromatic hydrocarbon benzolalpyrene is a known carcinogen found in soot and smoke. What is its structure?arrow_forward
- C17T04Q2945 Give the major product(s) of the following reaction. ? KMN04, H* heat OH CN OH There is no reaction under these conditions or the correct product is not listed here.arrow_forwardis steric hinderance not an issue here? why when reacting with KOC(CH3)3 does it yield 2-isopropyl-1-pentene and it yields 2,3-dimethyl-2hexene here?arrow_forwardC10T05Q3420 Give the major organic product for the following reaction. H H H catalytic heat if There is no reaction under these conditions or the correct product is not listed here.arrow_forward
- Draw the organic product of the following reaction. CH3 m-CICgH,CO;H • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, just draw one stereoisomer. • If more than one product is possible, only draw the major product. opy astearrow_forwardQuestão 10A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis resulted in CH3(CH2)4CO2H and HO2CCH2CH2CO2H as the only products. What is the reasonable structure for this hydrocarbon? Hexadec-6,10-dino undec-1,5-dino Hept-1,5-dino hex-1,5-dino naharrow_forwardC12T04Q8272 Give the major product(s) of the following reaction. CrO3 он H,SO4 H. of HO, OMe HO. There is no reaction under these conditions or the correct product is not listed here.arrow_forward
- Draw the structure of the alkene with the molecular formula CH10 that reacts with Br, to give this compound. CH3 Br Br • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. opyste ot pt pt pt ptarrow_forwardDraw a structural formula for the product formed upon hydroboration/oxidation of the alkene below. CH3CH2 C=CH2 CH3CH2 Use wedge and hash bonds ONLY for rings. Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. C P opy aste ○, [片arrow_forward18:45 1 Question 5 of 12 Reset 5Gº Submit Provide the correct IUPAC name for the skeletal (line-bond) structure shown here. Stereochemistry is ignored. 3- 2,3- 2,4- 4- 3,4- 2- iso di sec- tri) cyclo tert- hex hept) oct) [meth) pent] (eth yl yne ene ane Tap here or pull up for additional resourcesarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher: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