Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 6, Problem 6.20P

(a)

Interpretation Introduction

Interpretation:

The regio and stereoselectivity observe when 1- methylcyclopentene is treated with BH3 has to be explained.

Concept Introduction:

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.

If there are two different β-protons at a β-position of alkyl halide, then on the basis of stereoselectivity the trans-isomer is favored over cis-isomer.

Syn addition: When two substituents are added over double or triple bond on same side of the compound simultaneously is called syn addition.

Syn elimination: When two substituents bonded in same side of a compound gets cleaved from the substance simultaneously then the elimination is called syn elimination.

(b)

Interpretation Introduction

Interpretation:

The regio and stereoselectivity observe when 1- methylcyclopentene is treated with given reagent has to be explained.

Concept Introduction:

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.

If there are two different β-protons at a β-position of alkyl halide, then on the basis of stereoselectivity the trans-isomer is favored over cis-isomer.

Syn addition: When two substituents are added over double or triple bond on same side of the compound simultaneously is called syn addition.

Syn elimination: When two substituents bonded in same side of a compound gets cleaved from the substance simultaneously then the elimination is called syn elimination.

(c)

Interpretation Introduction

Interpretation:

The regio and stereoselectivity observe when 1- methylcyclopentene is treated with given reagent has to be explained.

Concept Introduction:

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.

If there are two different β-protons at a β-position of alkyl halide, then on the basis of stereoselectivity the trans-isomer is favored over cis-isomer.

Syn addition: When two substituents are added over double or triple bond on same side of the compound simultaneously is called syn addition.

Syn elimination: When two substituents bonded in same side of a compound gets cleaved from the substance simultaneously then the elimination is called syn elimination.

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Chapter 6 Solutions

Organic Chemistry

Ch. 6.5 - Prob. 6.11PCh. 6.5 - Prob. 6.12PCh. 6.5 - What alkene with the molecular formula C6H12, when...Ch. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Predict the organic product(s) of the reaction of...Ch. 6 - Prob. 6.18PCh. 6 - Prob. 6.20PCh. 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 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 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 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Show how to convert ethylene to these compounds....Ch. 6 - Show how to convert cyclopentene into these...Ch. 6 - Prob. 6.46PCh. 6 - Describe the stereochemistry of the bromohydrin...Ch. 6 - Prob. 6.49PCh. 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 - Prob. 6.53PCh. 6 - Prob. 6.54P
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