Give the main organic product of each reaction and name the electrophile…
Contributed by StemPy LabTry it on paper first. A hint, the key idea and the worked solution are here when you need them.
Give the main organic product of each reaction and name the electrophile.
- Benzene with 1-chloropropane and anhydrous aluminium chloride.
- Benzene with ethanoic anhydride and anhydrous aluminium chloride.
- Benzene with fuming sulphuric acid.
- Benzene with chlorine and aluminium chloride, in the dark.
- Benzene with a mixture of concentrated nitric acid and concentrated sulphuric acid, below .
Need a reminder? The key ideaShow
Electrophilic substitution of benzene: nitration (conc. and conc. ), halogenation ( with ), sulphonation (oleum), Friedel-Crafts alkylation and acylation ( or with anhydrous ). Alkylation can rearrange; acylation cannot. Sulphonation is reversible.
The worked solution
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Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.
(a) Isopropylbenzene (cumene), mainly. The propyl cation rearranges from primary to secondary before it attacks. The electrophile is .
(b) Acetophenone, . The electrophile is the acylium ion .
(c) Benzenesulphonic acid, . The electrophile is sulphur trioxide, .
(d) Chlorobenzene, . The electrophile is a chlorine atom made positive by the Lewis acid.
(e) Nitrobenzene, . The electrophile is the nitronium ion, .
Answer: cumene, acetophenone, benzenesulphonic acid, chlorobenzene and nitrobenzene.
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