OH 1. Hg(OAc)2, H2O 2. NaBH4 CH3 .CH3 H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H* adds to the sp? carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AcO-Hg-OAc AcO-Hg OAC

OH 1. Hg(OAc)2, H2O 2. NaBH4 CH3 .CH3 H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H* adds to the sp? carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AcO-Hg-OAc AcO-Hg OAC

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...

See similar textbooks

Similar questions

ОН 1. H(OAc)2, На0 2. NABH4 .CH3 CH3 H2C H3C Acid-catalyzed addition of water to an alkene yields an alcohol with Markovnikov regiochemistry. The electrophilic H adds to the sp carbon with the most hydrogens to yield the most stable carbocation intermediate, which then adds water to give the product alcohol. Because a carbocation intermediate is formed, rearrangements can occur prior to the addition of water. To avoid the possibility of rearrangement and still give a Markovnikov alcohol, alkenes can instead be treated with mercury(II) acetate in aqueous THF and then subsequently reduced with sodium borohydride. This reaction proceeds through a cyclic mercurinium ion intermediate which cannot rearrange. Water adds to the cyclic intermediate at the most substituted carbon to give an organomercury alcohol. The reduction step with sodium borohydride is complex and involves radicals. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing…
What reagent/reagents is/are necessary to transform the starting molecule into the desired product? SO3H ?
Synthesize the following from benzene.
A common alkene starting material is shown below. Predict the major product for each reaction. Ignore any inorganic byproducts. I I Select to Select to Draw I Draw I HBr Cl₂ H₂O 1. BH3-THF 2. H2O2, NaOH nd 1.03 2. (CH3)2S
Which is not an alkene formed when 2-chloro-2-methylbutane is dehydrohalogenated with NaOCH2CH3 (sodium ethoxide)? O 2-methyl-but-2-ene O 1-methylcyclobut-1-ene 2-methyl-but-1-ene
Draw a structural formula for the product formed upon hydroboration/oxidation of the alkene below. CH;CH2CH,CH2 C=CHCH3 CH;CH,CH,CH2
Kelerences Keview topic Draw a structural formula for the major product of the reaction shown. Cl2 H20 CH;CH2CH;CH=CHz • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. 2reg 2reg M) ots 2reg pts 2req 1 pts 2req 1 pts 2reg ...1 pts ChemDoodle Previous Next> Save and Exit APR tv MacBook Air 80 DII DD F3 F4 FS F6 F7 F8 F10 F1 F12 #3 $ & + 3 4 6. 7 8 %3D dele E Y | { } P [ F G H. J K C V N M ? .. .. * C0 B
9.
Alkyl Halides: Substitution reaction with bromomethane and CH3NH2 Part A Draw the product formed when the structure shown below undergoes a substitution with CH3NH₂. Interactive 3D display mode H3C Br
A. In the following reaction, the alkene is acting as a/n + B. In the following reaction, water is acting as a/n CCH3 + H20: HOCHCH3 + H3o
TReview TOpics] [References Draw a structural formula for the major product of the reaction shown. CH3 CH3CHCH=CH2 Show product steréochemistry IF the reactant alkene has both carbons of the double bond within a • Do not show stereochemistry in other cases. If the reaction produces a racemic mixture, just draw one stereoisomer. C P opy aste C.
Just to reiterate, the question is to draw out all possible alkene reactants that will result in the shown product.