Chapter 5, Problem 5.76P

Interpretation Introduction

(a)

Interpretation:

It is to be identified which two hydrogen atoms in $\text{2, 3-dibromoprop-1-ene}$ (${\text{C}}_3{\text{H}}_{4}B{r}_2$) can be replaced by $Cl$ atoms to yield constitution isomers having molecular formula ${\text{C}}_3{\text{H}}_3{\text{Br}}_2\text{Cl}$.

Concept introduction:

Constitutional isomers are the isomers having the same molecular formula but different connectivity. For the given structure, replacing the hydrogen atoms by halogen atoms attached to different carbon atoms would generate constitutional isomers.

Interpretation Introduction

(b)

Interpretation:

It is to be identified which two hydrogen atoms in $\text{2, 3-dibromoprop-1-ene}$ (${\text{C}}_3{\text{H}}_{4}B{r}_2$) can be replaced by $Cl$ atoms to yield enantiomers having molecular formula ${\text{C}}_3{\text{H}}_3{\text{Br}}_2\text{Cl}$.

Concept introduction:

Configurational isomers are the stereoisomers which have the same connectivity of atoms and which can’t be interconverted by rotations around single bonds. Enantiomers are the type of constitutional isomers, which are non-superimposable mirror images of each other. For the given structure, replacing hydrogen atoms on wedge and dash bond by halogen atoms attached to the same carbon atoms would generate enantiomers.

Interpretation Introduction

(c)

Interpretation:

It is to be identified which two hydrogen atoms in $\text{2, 3-dibromoprop-1-ene}$ (${\text{C}}_3{\text{H}}_{4}B{r}_2$) can be replaced by $Cl$ atoms to yield diastereomers of ${\text{C}}_3{\text{H}}_3{\text{Br}}_2\text{Cl}$.

Concept introduction:

Configurational isomers are the stereoisomers which have the same connectivity of atoms and which can’t be interconverted by rotations around single bonds. Diastereomers are the type of constitutional isomers which are not mirror images of each other. Cis-trans isomers are diastereomers of each other. Cis isomers are the ones in which two top-priority substituents are linked to the same side of the double bond. Trans isomers are the ones in which two top-priority substituents are attached to the opposite sides of the double bond. For any given structure, replacing hydrogen atoms attached to any one doubly bonded carbon atom would generate diastereomers.