Question

Write a structural formula for the product from Friedel-Crafts alkylation or acylation of benzene with each compound. (a) CC(C)(C)C(=O)Cl (b) CCCCl (c) CC(Cl)c1ccccc1

Short answer

1. For compound (a) tert-butyl chloroacetate, the product formed when benzene undergoes Friedel-Crafts acylation is a ketone with the structural formula: c1(ccccc1)C(=O)C(C)(C)C 2. For compound (b) 1-chlorobutane, the product formed when benzene undergoes Friedel-Crafts alkylation is an alkyl substituted benzene with the structural formula: C1(=CC=CC=C1)CCCC 3. For compound (c) 2-chloropropylbenzene, the product formed when benzene undergoes Friedel-Crafts alkylation is an alkyl substituted benzene with the structural formula: C1(=CC=C(C=C1)C)CC

Step-by-step solution

Identify Reactant and Reaction Type

The reactant is given by the SMILES notation "CC(C)(C)C(=O)Cl", which corresponds to tert-butyl chloroacetate. The presence of an acid chloride group (C(=O)Cl) tells us that this is a Friedel-Crafts acylation reaction.

Determine the Electrophile

In Friedel-Crafts acylation reactions, the electrophile is an acylium ion, which is formed through the reaction of the acid chloride with a Lewis acid catalyst (such as AlCl3). For tert-butyl chloroacetate, the electrophile will be the tert-butyl acylium ion: [(CH3)3C-C(=O)+].

Write the Structural Formula for the Product

In the final step of a Friedel-Crafts acylation, the electrophile (tert-butyl acylium ion) replaces a hydrogen atom on the benzene ring through electrophilic aromatic substitution. Therefore, the resulting structural formula for the acylation product is given by: c1(ccccc1)C(=O)C(C)(C)C For compound (b):

Identify Reactant and Reaction Type

The reactant is given by the SMILES notation "CCCCl", which corresponds to 1-chlorobutane. As this compound contains an alkyl halide, a Friedel-Crafts alkylation reaction will occur.

Determine the Electrophile

In Friedel-Crafts alkylation reactions, the electrophile is typically an alkyl carbocation, which is formed by reacting the alkyl halide with a Lewis acid catalyst (such as AlCl3). In the case of 1-chlorobutane, the electrophile will be the butyl carbocation: [CH3CH2CH2CH2+].

Write the Structural Formula for the Product

In the final step of a Friedel-Crafts alkylation, the electrophile (butyl carbocation) replaces a hydrogen atom on the benzene ring through electrophilic aromatic substitution. Therefore, the resulting structural formula for the alkylation product is: C1(=CC=CC=C1)CCCC For compound (c):

Identify Reactant and Reaction Type

The reactant is given by the SMILES notation "CC(Cl)c1ccccc1", which corresponds to 2-chloropropylbenzene. As this compound also contains an alkyl halide, a Friedel-Crafts alkylation reaction will occur.

Determine the Electrophile

In this case, the electrophile will be the 2-propyl carbocation, which is formed by reacting 2-chloropropylbenzene with a Lewis acid catalyst (such as AlCl3). The electrophile is given by the structure: [CH3CH2CH+].

Write the Structural Formula for the Product

In the final step of a Friedel-Crafts alkylation, the electrophile (2-propyl carbocation) replaces a hydrogen atom on the benzene ring through electrophilic aromatic substitution. Therefore, the resulting structural formula for the alkylation product is: C1(=CC=C(C=C1)C)CC