Quiz - Benzene Derivatives | Electrophilic Substitution of Benzene Derivatives

Organic Chemistry 2 - Quiz - Benzene Derivatives


Which of the following reactions is not an electrophilic aromatic substitution?

Benzyne is generated by the dehalogenation of 2-bromofluorobenzene by magnesium


When considering electrophilic substitution reactions, halides are described as:

Halides are deactivating groups and ortho/para directing. Please note, deactivating groups are generally meta directing


When considering electrophilic substitution reactions, methoxy substituent is described as:

D ⇒ Donor:
- NH2, OH (strongly activating)
- NHCOR, OR (moderately activating) ⇒ ex: methoxy substituent
- alkyl, aryl (weakly activating)


When considering electrophilic substitution reactions, nitro substituent is described as:

Nitro substituent: NO2

A ⇒ Acceptor:
- N+R3, NO2, CF3, CN, SO3H (strongly deactivating)
- COH, COR, COOH, COOR, CONH2 (moderately deactivating)


Which substituent is the strongest activator?

NH(strongly activating) > MeO (moderately activating) > Br (moderately deactivating) > NO2 (strongly deactivating)


What is the best synthetic strategy for alkylating bromobenzene in the ortho position?

Br substituent is ortho/para directing.  Because of the sterics, the para product will be preferred over the ortho product. In order to alkylate bromobenzene in the ortho position, the para position must be locked. A sulfonation of the para positon could be a good strategy: