Question 21 In the standard electrophilic addition of a hydrohalide (H-X) to an alkene, what can be said about the stereochemistry of the product? O The stereochemistry will be anti, since the sigma bond will rotate once the pi bond is broken OThe stereochemistry will be syn, since the nucleophile will be generated on the same side of the alkene as the electrophile. O The stereochemistry will be random, since the carbocation generated is planar and attack can come from either side. O None of these, because it is not possible to generate a chiral center with stereochemistry through an electrophilic addition reaction

Question 21 In the standard electrophilic addition of a hydrohalide (H-X) to an alkene, what can be said about the stereochemistry of the product? O The stereochemistry will be anti, since the sigma bond will rotate once the pi bond is broken OThe stereochemistry will be syn, since the nucleophile will be generated on the same side of the alkene as the electrophile. O The stereochemistry will be random, since the carbocation generated is planar and attack can come from either side. O None of these, because it is not possible to generate a chiral center with stereochemistry through an electrophilic addition reaction

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 8E

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What about the second step in the electrophilic addition of HCl to an alkene-the reaction of chloride ion with the carbocation intermediate? Is this step exergonic or endergonic? Does the transition state for this second step resemble the reactant (carbocation) or the product (alkyl chloride)? Make a rough diagram of what the transition state may look like?
In the elimination reaction of an alkyl halide, what happens to the leaving group and what’s the product?
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:
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