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Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350

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BuyFindarrow_forward

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Chapter 6, Problem 6.29P
Textbook Problem
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Propose a mechanism for this reaction and account for its regioselectivity.

Chapter 6, Problem 6.29P, Propose a mechanism for this reaction and account for its regioselectivity.

Interpretation Introduction

Interpretation: The mechanism for given reaction has to be proposed and its regioselectivity has to be accounted.

Concept introduction:

Electrophilic addition reaction is an addition reaction where in a chemical bond, a Π bond is Brocken and two new σ bonds are formed, the substrate of an electrophilic addition reaction must have a double bond or triple bond.

Carbocation: The carbon ion that bears a positive charge on it.

Nucleophile: donates pair of electrons to positively charged substrate resulting in the formation of chemical bond.

Electrophile: accepts pair of electrons from negatively charged substrate results in chemical bond formation.

Consider elimination reaction where alkenes are formed when alkyl halides are treated with bases via eliminating one β-proton and one α-halo group of the alkyl halide.

The product of the elimination reaction is depends upon the β-positions of alkyl halide.  If the β-positions are identical and the products formed are also identical.  If the β-positions are different and the products formed are also different.  This means the double bond can form in two different regions so this type of reaction is called regioselective and the products are called as regiochemical outcomes.

Explanation of Solution

The mechanism for given reaction is as follows,

  1. 1. First, the positive portion that is iodine of unsymmetrical electrophilic reagent I-Cl gets added to the carbon-carbon double bond and forms more stable intermediate A.
  2. 2

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Chapter 6 Solutions

Organic Chemistry
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Ch. 6.5 - Use a balanced half-reaction to show that each...Ch. 6.5 - Tell which of these transformations are oxidations...Ch. 6.5 - What alkene with the molecular formula C6H12, when...Ch. 6 - Draw structural formulas for the isomeric...Ch. 6 - Arrange the alkenes in each set in order of...Ch. 6 - Predict the organic product(s) of the reaction of...Ch. 6 - Draw a structural formula of an alkene that...Ch. 6 - Account for the regioselectivity and...Ch. 6 - Draw a structural formula for an alkene with the...Ch. 6 - Account for the fact that addition of HCl to...Ch. 6 - Account for the fact that treating propenoic acid...Ch. 6 - Draw a structural formula for the alkene with the...Ch. 6 - Draw the alternative chair conformations for the...Ch. 6 - Draw a structural formula for the cycloalkene with...Ch. 6 - Reaction of this bicycloalkene with bromine in...Ch. 6 - Terpin, prepared commercially by the...Ch. 6 - Propose a mechanism for this reaction and account...Ch. 6 - Treating 2-methylpropene with methanol in the...Ch. 6 - When 2-pentene is treated with Cl2 in methanol,...Ch. 6 - Treating cyclohexene with HBr in the presence of...Ch. 6 - Propose a mechanism for this reaction. 1-Pentane...Ch. 6 - Treating 4-penten-1-ol with bromine in water forms...Ch. 6 - Provide a mechanism for each reaction.Ch. 6 - Treating 1-methyl-1-vinylcyclopentane with HCl...Ch. 6 - Reaction of -pinene with borane followed by...Ch. 6 - Write structural formulas for the major organic...Ch. 6 - Draw the structural formula of the alkene that...Ch. 6 - Consider the following reaction. (a) Draw a...Ch. 6 - Predict the major organic product(s) of the...Ch. 6 - The heat of hydrogenation of...Ch. 6 - Show how to convert ethylene to these compounds....Ch. 6 - Show how to convert cyclopentene into these...Ch. 6 - State the number and kind of stereoisomers formed...Ch. 6 - Describe the stereochemistry of the bromohydrin...Ch. 6 - The 2-propenyl cation appears to be a primary...Ch. 6 - Treating 1,3-butadiene with 1 mole of HBr gives a...Ch. 6 - In this chapter, we studied the mechanism of the...Ch. 6 - As we have seen in this chapter, carbon-carbon...Ch. 6 - Following is an example of a type of reaction...Ch. 6 - We now introduce the concept of an organic...

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