Q20AP - Organic Chemistry (Mcmurry)

Question

Draw and name all possible isomers of the following: 

1. Dinitrobenzene
2. Bromo dimethyl benzene 
3. Trinitrophenol

Step-by-Step Solution

Answer

Answer

(a) 

Ortho-dinitrobenzene or

 1,2-dinitrobenzene

b)

1-bromo-2,3-dimethylbenzene

(c) 

2,3,4-trinitrophenol

Step-by-Step Solution Step 1: Dinitrobenzene

The presence of two nitro groups on the benzene ring is called dinitrobenzene. These nitro groups may be positioned at either 1,2; 1,3; and 1,4. If it is positioned 1,2 then it is ortho-dinitrobenzene, if it is positioned 1,3 then it is meta-dinitrobenzene, and if it is 1,4 then it is para-dinitrobenzene.

Step 2: Isomers of dinitrobenzene

There are three isomers of dinitrobenzene that are ortho, meta, and para dinitrobenzene which is represented as follows:

Ortho-dinitrobenzene or

 1,2-dinitrobenzene

Meta-dinitrobenzene or 

1,3-dinitrobenzene

Para-dinitrobenzene or 

1,4-dinitrobenzene

Step 3: Bromo dimethyl benzene

The presence of the bromo group and two methyl groups on the benzene ring is referred to as Bromo dimethyl benzene. The position of the bromine group and two methyl groups varies forming many isomers of the compound

Step 4: Isomers of Bromo dimethyl benzene

There are six isomers of bromo dimethyl benzene shown as follows:

1-bromo-2,3-dimethylbenzene

1-bromo-2,4-dimethylbenzene

2-bromo-1,4-dimethylbenzene

2-bromo-1,3-dimethylbenzene

4-bromo-1,2-dimethylbenzene

1-bromo-3,5-dimethylbenzene

Step 5: Trinitrophenol

The presence of the OH group and three nitro groups on the benzene ring is referred to as trinitrophenol. The position of the hydroxyl group and three nitro groups varies forming many isomers of the compound.

Step 6: Isomers of Trinitrophenol

There are six isomers of trinitrophenol shown as follows:

2,3,4-trinitrophenol

3,4,5-trinitrophenol

2,4,6-trinitrophenol

2,3,5-trinitrophenol

2,3,6-trinitrophenol

2,4,5-trinitrophenol