Write structural formulas for the following compounds

1.) Write structural formulas for the following compounds:

2,5-dichlorobenzoic acid

m-bromoacetophenone

2,4,6-trichlorotoluene

m-fluorostyrene

p-tert-butylaniline

2.) What are the main mononitro products of the nitration of the following compounds:

propylbenzene

3-ethyltoluene

3.) Write out all steps in the mechanism for the reaction of

benzene + nitric acid (H2SO4 catalyst) -------->

toluene + bromine (FeBr3 catalyst -------->

4.) Draw all possible contributing structures to the carbocation intermediate in the bromination of phenol. Explain why the major products are o- and p-bromophenol.

5.) Indicate the main monosubstitution products in each of the following reactions. Keep in mind that certain substituents are meta-directing and others are ortho, para-directing.

nitrobenzene + chlorine (Fe catalyst) -------->

benzoic acid + concentrated nitric acid (heat) --------->

aniline + bromine (Fe catalyst)--------->

toluene + concentrated sulfuric acid (heat) -------->

6.) Using benzene or toluene as the only aromatic organic starting material, devise a synthesis for each of the following:

o-chlorotoluene

3-bromonitrobenzene

p-toluenesulfonic acid

2-chloronitrobenzene

7.) Predict whether the following substituents on the benzene ring are likely to be ortho, para-directing or meta-directing and whether they are likely to be ring-activating or ring-deactivating.

----N(CH3)2

O
||
----C-CH3

----CH2CH3

8.) Which compound is more reactive toward electrophilic substitution (e.g., nitration)? Explain your reasoning.

toluene or nitrobenzene

bromobenzene or nitrobenzene

9.) For a one-step synthesis of 2-chlorobenzenesulfonic acid, which is a better starting material: chlorobenzene or benzenesulfonic acid?