Concept:
The hybridization of a carbon atom depends on the types of bonds it forms:
- $sp^3$ hybridization: Carbon is bonded to 4 atoms via single bonds only.
- $sp^2$ hybridization: Carbon is bonded to 3 atoms (contains 1 double bond).
- $sp$ hybridization: Carbon is bonded to 2 atoms (contains 1 triple bond, or 2 double bonds).
Step 1: Draw the structure of hexa-1,4-diyne.
The name "hexa-1,4-diyne" indicates a 6-carbon chain ("hex") with triple bonds ("diyne") starting at carbon 1 and carbon 4.
Structure: $CH \equiv C - CH_2 - C \equiv C - CH_3$
Let's number the carbons from left to right:
$$^1CH \equiv ^2C - ^3CH_2 - ^4C \equiv ^5C - ^6CH_3$$
Step 2: Determine the hybridization of each carbon atom.
- $C_1$ has a triple bond with $C_2 \implies sp$ hybridized.
- $C_2$ has a triple bond with $C_1 \implies sp$ hybridized.
- $C_3$ has single bonds only (to $C_2$, $C_4$, and two $H$'s) $\implies sp^3$ hybridized.
- $C_4$ has a triple bond with $C_5 \implies sp$ hybridized.
- $C_5$ has a triple bond with $C_4 \implies sp$ hybridized.
- $C_6$ has single bonds only (to $C_5$ and three $H$'s) $\implies sp^3$ hybridized.
Step 3: Count the $sp^2$ hybridized carbons.
Reviewing the list above, there are four $sp$ hybridized carbons and two $sp^3$ hybridized carbons.
There are no double bonds in the molecule, so there are
zero $sp^2$ hybridized carbon atoms.
Thus, one mole of hexa-1,4-diyne contains zero moles of $sp^2$ hybridized carbon atoms.