Chapter 12, Problem 12.6P

Interpretation Introduction

(a)

Interpretation:

The products that would be produced when the given compound reacts with molecular bromine in carbon tetrachloride, are to be drawn. It is also to be predicted if the product mixture will be optically active or not.

Concept introduction:

Alkene reacts with molecular bromine $\left({\text{Br}}_{\text{2}}\right)$ in carbon tetrachloride ${\text{(CCl}}_{\text{4}}\text{)}$ to yield a mixture of dihaloalkanes. Molecular bromine undergoes anti addition across a carbon-carbon double bond. To account for the stereochemistry of the reaction, the mechanism must proceed through a cyclic halonium ion intermediate. If the mixture of products is diastereomers, then the mixture would be optically active. If the products are either enantiomers or a meso compound, then the mixture is optically inactive. A symmetrically substituted alkene may yield a meso compound, which would be optically inactive.

Interpretation Introduction

(b)

Interpretation:

The products that would be produced when the given compound reacts with molecular bromine in carbon tetrachloride, are to be drawn. It is also to be predicted if the product mixture will be optically active or not.

Concept introduction:

Alkene reacts with molecular bromine $\left({\text{Br}}_{\text{2}}\right)$ in carbon tetrachloride ${\text{(CCl}}_{\text{4}}\text{)}$ to yield a mixture of dihaloalkanes. Molecular bromine undergoes anti addition across a carbon-carbon double bond. To account for the stereochemistry of the reaction, the mechanism must proceed through a cyclic halonium ion intermediate. If the mixture of products is diastereomers, then the mixture would be optically active. If the products are either enantiomers or a meso compound, then the mixture is optically inactive A symmetrically substituted alkene may yield a meso compound, which would be optically inactive. While an unsymmetrically substituted alkene is expected to yield a pair of diastereomers making the mixture optically active.

Interpretation Introduction

(c)

Interpretation:

The products that would be produced when the given compound reacts with molecular bromine in carbon tetrachloride are to be drawn. It is also to be predicted if the product mixture will be optically active or not.

Concept introduction:

Alkene reacts with molecular bromine $\left({\text{Br}}_{\text{2}}\right)$ in carbon tetrachloride ${\text{(CCl}}_{\text{4}}\text{)}$ to yield a mixture of dihaloalkanes. Molecular bromine undergoes anti addition across a carbon-carbon double bond. To account for the stereochemistry of the reaction, the mechanism must proceed through a cyclic halonium ion intermediate. If the mixture of products is diastereomers, then the mixture would be optically active. If the products are either enantiomers or a meso compound, then the mixture is optically inactive. A symmetrically substituted alkene may yield a meso compound, which would be optically inactive. While an unsymmetrically substituted alkene is expected to yield a pair of diastereomers making the mixture optically active.

Interpretation Introduction

(d)

Interpretation:

The products that would be produced when the given compound reacts with molecular bromine in carbon tetrachloride are to be drawn. It is also to be predicted if the product mixture will be optically active or not.

Concept introduction:

Alkene reacts with molecular bromine $\left({\text{Br}}_{\text{2}}\right)$ in carbon tetrachloride ${\text{(CCl}}_{\text{4}}\text{)}$ to yield a mixture of dihaloalkanes. Molecular bromine undergoes anti addition across a carbon-carbon double bond. To account for the stereochemistry of the reaction, the mechanism must proceed through a cyclic halonium ion intermediate. If the mixture of products is diastereomers, then the mixture would be optically active. If the products are either enantiomers or a meso compound, then the mixture is optically inactive. A symmetrically substituted alkene may yield a meso compound, which would be optically inactive. While an unsymmetrically substituted alkene is expected to yield a pair of diastereomers making the mixture optically active.