4. Evidence for the intermediate carbocation in the acid-catalyzed dehydration of alcohols comes from theobservation that rearrangements sometimes occur. Propose a mechanism to account for the formation of2,3-dimethyl-2-butene from 3,3-dimethyl-2-butanol.УхоH2SO4OHH+ H₂O

To propose a mechanism for the formation of 2,3-dimethyl-2-butene from 3,3-dimethyl-2-butanol via…

Answered: 4. Evidence for the intermediate…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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9.
The following reaction is similar to the dehydration of 2-methylcyclohexanol. However, a significant amount of a tetrasubstituted alkene is expected. Predict the structure for this tetrasubstituted alkene. Also, using curved arrows, provide a reasonable mechanism for its formation. Но. H3PO4 ??? A (-H2O)
CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:
Draw a structural formula for the major organic product of the following reaction: CH3- -CH=CHCOH + Cl₂ CH₂Cl2
The acid-catalyzed hydration of 3,3-dimethyl-1-butene gives 2,3-dimethyl- 2- butanol as the major product. Propose a mechanism for the formation of this alcohol
When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.
Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodomethane with the following alkoxide ion: CH3 H3C O Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. орy вste ChemDoodle
Organometallic reagents such as sodium acetylide undergo an addition reaction with ketones, giving alcohols: он 1. Na+ -:CCH 2. H30* C-C=CH How might you use this reaction to prepare 2-methyl-1,3-butadiene?
Complete the following steps of the reaction using proper stereochemistry, using all the wedge and dash diagrams and also state if the resulting solutions of the products are optically active.
4. What alkenes might be formed by the dehydration of the following alcohols? If more than one product is possible, write them all and then indicate which you expect to predominate. но сн, A) CH,CH2CHCHCH3 сHз ОН -ҫнCH,CH, OH

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4. Evidence for the intermediate carbocation in the acid-catalyzed dehydration of alcohols comes from the observation that rearrangements sometimes occur. Propose a mechanism to account for the formation of 2,3-dimethyl-2-butene from 3,3-dimethyl-2-butanol. Ухо H2SO4 OH H + H₂O