Consider the following systematic series of organic halogen compounds: 1. Benzyl chloride 2. Allyl c — Haloalkanes and Haloarenes Chemistry Question
Question
Consider the following systematic series of organic halogen compounds: 1. Benzyl chloride 2. Allyl chloride 3. Vinyl chloride 4. Chlorobenzene 5. 1-chlorobutane How many of these compounds specifically feature a $C-Cl$ bond where the carbon atom directly bonded to the chlorine is $sp^2$ hybridized?
💡 Solution & Explanation
We must inspect the hybridization of the specific carbon atom attached to the chlorine atom. 1. Benzyl chloride ($Ph-CH_2-Cl$): The Cl is attached to a methylene group, which is $sp^3$ hybridized. 2. Allyl chloride ($CH_2=CH-CH_2-Cl$): The Cl is attached to an $sp^3$ carbon adjacent to the double bond. 3. Vinyl chloride ($CH_2=CH-Cl$): The Cl is attached directly to the double-bonded carbon, which is $sp^2$ hybridized. 4. Chlorobenzene ($Ph-Cl$): The Cl is attached directly to the aromatic ring, making the carbon $sp^2$ hybridized. 5. 1-chlorobutane ($CH_3CH_2CH_2CH_2-Cl$): The Cl is attached to an aliphatic alkane carbon, which is $sp^3$ hybridized. Only vinyl chloride and chlorobenzene feature an $sp^2$ hybridized $C-Cl$ bond. Total = 2.