Question

Draw the structural formula for at least one bromoalkene with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Br}\) that shows: (a) Neither \(E, Z\) isomerism nor chirality. (b) \(E, Z\) isomerism but not chirality. (c) Chirality but not \(E, Z\) isomerism. (d) Both chirality and \(E, Z\) isomerism.

Short answer

Question: Provide the structural formulas for bromoalkenes with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Br}\) that satisfy the following conditions: a) Neither E, Z isomerism nor chirality. b) E, Z isomerism but not chirality. c) Chirality but not E, Z isomerism. d) Both chirality and E, Z isomerism.

Step-by-step solution

(a) Neither E, Z isomerism nor chirality

For this compound, we need a structure with no cis-trans isomerism and no chiral centers. One way to achieve this is by having a symmetrical bromoalkene. The structure is: ``` H H Br H H | | | | | H-C-C=C-C-H ``` This compound has only one isomer, and all carbon atoms have at least two hydrogen atoms which means there is no chiral center.

(b) E, Z isomerism but not chirality

For this compound, we need a structure with \(E, Z\) isomerism but no chiral center. One such structure can be: ``` H Br H H H | | | | | H-C-C=C-C-H ``` In this compound, we have cis-trans isomerism around the C=C double bond, but there are no carbon atoms with 4 different groups attached, so there are no chiral centers.

(c) Chirality but not E, Z isomerism

For this compound, we need a structure with a chiral center but no \(E, Z\) isomerism. One such structure can be: ``` H H H H Br | | | | | H-C-C=C-C-H ``` In this compound, there is no cis-trans isomerism around the C=C double bond, but the last carbon atom is chiral as it has a hydrogen, a bromine, and two different alkyl groups attached to it.

(d) Both chirality and E, Z isomerism

For this compound, we need a structure that shows both chirality and \(E, Z\) isomerism. One such structure can be: ``` H Br H H Br | | | | | H-C-C=C-C-H ``` In this compound, we have cis-trans isomerism around the C=C double bond. The last carbon atom is chiral as it has a hydrogen, a bromine, and two different alkyl groups attached to it.