Draw all the structural and geometrical (cis–trans) isomers of bromochloropropene.

Short Answer

Expert verified
The molecular formula for bromochloropropene is C3H5BrCl. There are two possible structural isomers: 1-bromo-2-chloropropene and 1-bromo-3-chloropropene. For 1-bromo-2-chloropropene, there are two geometrical isomers: cis-1-bromo-2-chloropropene (Br and Cl on the same side of the double bond) and trans-1-bromo-2-chloropropene (Br and Cl on opposite sides of the double bond). However, 1-bromo-3-chloropropene does not have cis-trans isomers. Altogether, we have 3 isomers for bromochloropropene.

Step by step solution

01

Understand structural and geometrical isomers

Structural isomers are isomers that have the same molecular formula but have a different arrangement of atoms in the molecule. Geometrical isomers, also known as cis–trans isomers, are a type of stereoisomers that exhibit different spatial orientations of substituents around a rigid bond or structure. Now that we understand the types of isomers, we will identify the molecular formula for bromochloropropene, and then draw all the possible isomers.
02

Identify the molecular formula for bromochloropropene

Bromochloropropene has one bromine atom, one chlorine atom, and three carbon atoms (in propene). Hence, the molecular formula for bromochloropropene is C3H5BrCl.
03

Draw all structural isomers

To draw the structural isomers, we need to consider all the possible arrangements of the bromine and chlorine atoms in the propene molecule. There are two possible structural isomers for bromochloropropene: 1. 1-bromo-2-chloropropene: Bromine is attached to the first carbon, and chlorine is attached to the second carbon. 2. 1-bromo-3-chloropropene: Bromine is attached to the first carbon, and chlorine is attached to the third carbon.
04

Draw all geometrical isomers (cis–trans) for each structural isomer

Now that we have identified the structural isomers, we will draw the cis–trans isomers for each of them. For 1-bromo-2-chloropropene: 1. Cis-1-bromo-2-chloropropene: The bromine and chlorine atoms are on the same side of the double bond. (The hydrogens are also on the same side of the double bond.) 2. Trans-1-bromo-2-chloropropene: The bromine and chlorine atoms are on opposite sides of the double bond. (The hydrogens are also on opposite sides of the double bond.) For 1-bromo-3-chloropropene: 1-bromo-3-chloropropene does not have a cis–trans isomer since the bromine and chlorine atoms are not adjacent to each other and there is no restricted rotation around the double bond. So, we have a total of 3 isomers: 2 structural isomers and 1 geometrical isomer (trans-1-bromo-2-chloropropene).

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