The regio and stereoselectivity observe when 1- methylcyclopentene is treated with BH 3 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.

Question

3. From what Grignard reagent and carbonyl compound are the following alcohols are prepared? (a) (b) CH₂OH H* CH₂O -CH3 OH -CH3

Answer 1

Question

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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3. From what Grignard reagent and carbonyl compound are the following alcohols are prepared? (a) (b) CH₂OH H* CH₂O -CH3 OH -CH3

(a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?

(a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.

Answer 2

Question

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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Answer 3

Question

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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Answer 4

Question

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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Answer 5

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.

Answer 6

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.

Answer 7

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.

Answer 8

(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.

Answer 9

(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.

Answer 10

(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.

Answer 11

(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.

Answer 12

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Ch. 6.2 - Using the BDE values from Appendix 3, calculate...Ch. 6.3 - Name and draw a structural formula for the product...Ch. 6.3 - Prob. 6.3P Ch. 6.3 - Propose a mechanism for the addition of HI to...Ch. 6.3 - Prob. 6.5P Ch. 6.3 - Propose a mechanism for the acid-catalyzed...Ch. 6.3 - The acid-catalyzed hydration of...Ch. 6.3 - Complete these reactions. (a) (b)Ch. 6.3 - Draw the structure of the chlorohydrin formed by...Ch. 6.4 - Draw structural formulas for the alkene that gives...

Solution Summary: The author explains the regio and stereoselectivity observed when 1- methylcyclopentene is treated with

Chapter 6 Solutions