Consider the molecule C3H6Cl2, which is derived from propane, C3H8, by substituting two Cl atoms for H atoms. Draw the structural isomers of C3H6Cl2.

Question

Consider the molecule [latex]C_{3}H_{6}Cl_{2}[/latex], which is derived from propane, [latex]C_{3}H_{8}[/latex], by substituting two Cl atoms for H atoms. Draw the structural isomers of [latex]C_{3}H_{6}Cl_{2}[/latex].

Accepted Answer

1. All these compounds have three carbon atoms, hence the same skeleton.

C-C-C

Note that the terminal C atoms are equivalent. The middle C atom is not.

2. Bond 2 Cl atoms to the second C atom for the first isomer, and 2 Cl atoms to the terminal C atom for the second isomer.

[latex]C-\overset{\underset{|}{Cl} }{\underset{\overset{|}{Cl} }{C}}-C [/latex] and [latex]C-C-\overset{\underset{|}{Cl} }{\underset{\overset{|}{Cl} }{C}}[/latex]

3. Bond a Cl atom to each terminal C atom for the third isomer.

[latex]\overset{\underset{|}{Cl} }{C}-C- \overset{\underset{|}{Cl} }{C}[/latex]

4. Bond a Cl atom to a terminal C atom and the other Cl atom to the middle C atom for the fourth isomer.

[latex]\overset{\underset{|}{Cl} }{C}- \overset{\underset{|}{Cl} }{C}-C-[/latex]

5. Add the appropriate number of H atoms to the C atoms so that there are four bonds around each C atom.

[latex]CH_{3}-CH_{2}-\overset{\underset{|}{Cl} }{\underset{\overset{|}{Cl} }{C}} -H[/latex] [latex]CH_{3}-\overset{\underset{|}{Cl} }{\underset{\overset{|}{Cl} }{C}}-CH_{3} [/latex] [latex]H-\overset{\underset{|}{H} }{\underset{\overset{|}{Cl} }{C}}-CH_{2}-\overset{\underset{|}{H} }{\underset{\overset{|}{Cl} }{C}}-H[/latex] [latex]CH_{3}-\overset{\underset{|}{H} }{\underset{\overset{|}{Cl} }{C}}-\overset{\underset{|}{H} }{\underset{\overset{|}{Cl} }{C}}-H[/latex]

Question 22.9: Consider the molecule C3H6Cl2, which is derived from propane...

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