1.

Generate names for these structures

a.

b.

c.

d.

e.

f.
g.

2. Generate structures from given names

a.

b.

c.

d.

3a. Calculation of Heat of Formation

a. Octane
Heat Of Formation = -208.45 kJ/mol
b. 2-methylheptane
Heat Of Formation = -213.73 kJ/mol
c. 2,2-dimethylhexane
Heat Of Formation = -217.2 kJ/mol
d. 2,2,3,3-tetramethylbutane
Heat Of Formation = -225.95 kJ/mol
Report: List the isomeric alkanes in order of stability from most stable to least
stable.
1.) 2,2,3,3-tetramethylbutane (most stable). Heat Of Formation = -225.95
kJ/mol
2.) 2,2-dimethylhexane. Heat Of Formation = -217.2 kJ/mol
3.) 2-methylheptane. Heat Of Formation = -213.73 kJ/mol
4.) Octane (least stable). Heat Of Formation = -208.45 kJ/mol
*Branched alkanes are lower in energy and more stable than straight-chain alkanes.
3b. Calculation of boiling point
a. Octane
Boiling point = 393.054 Kelvin
b. 2-methylheptane
Boiling Point = 378.865 Kelvin
c. 2,2-dimethylhexane
Boiling Point = 369.357 Kelvin
d. 2,2,3,3-tetramethylbutane
Boiling Point = 344.756 Kelvin
Report: Explain why the isomeric alkanes have different boiling points.
Different boiling points among the alkanes are present because some are
more branched than others are, and one has no branching. This is significant
because branching plays a major role in boiling point. A branched hydrocarbon
generally has a small surface area compared to straight chains. Thus, branching
causes a decrease in boiling point. Because 2,2,3,3-tetramethylbutane has the most
branching, its boiling point is the lowest at 344.756 Kelvin. The hydrocarbon with
the second most branching is 2,2-dimethylhexane with a boiling point of 369.357
Kelvin. 2-methylheptane only has one branch so its boiling point of 378.865 Kelvin is
higher than the other two. Lastly, octane has no branching so its boiling point is the
highest at 393.054 Kelvin.

3c. Calculation of water solubility

a. 1-octanol
Water Solubility
b. 1-hexanol
Water Solubility
c. 1-butanol
Water Solubility
d. Ethanol
Water Solubility
e. Diethyl ether
Water Solubility

= 540 mg/L
= 6000 mg/L
= 74000 mg/L
= 1000000 mg/L
= 54950 mg/L

Report: Explain the differences in water solubility.

Alcohols have hydrophobic and hydrophilic regions. The hydrophilic region is
associated with hydrogen bonding which is what makes that part of the molecule
soluble. As the size of the hydrophobic region increases, the water solubility
decreases. 1-Octanol has a larger hydrophobic region than 1-hexanol because it has
a longer chain, which is why 1-hexanol has a water solubility of 6000mg/L and 1octanol has a water solubility of 540mg/L. As you can tell, 1-hexanol is more soluble
than 1-octanol. The same goes for 1-butnaol. Its water solubility is 74000mg/L and
only has a four-carbon chain, making its hydrophobic region smaller than 1-hexanol
and 1-octanol, also making it more soluble than the two. Ethanol has a water
solubility of 1000000mg/L and is said to be miscible in water. Lastly, Diethyl ether is
a common solvent. It has a water solubility of 54950mg/L and can dissolve a wide
range of compounds.
4a. Calculate bond angles
a. Water (H-O-H angle)
104.159
b. Dimethyl Ether (C-O-C angle)
111.854
c. 2-(tert-butoxy)-2-methylpropane (C-O-C angle)
123.517
Report: Explain why the bond angles are different.
In each bond angle, an oxygen atom is present. The oxygen atom is sp3
hybridized and the atoms around it are generally arranged in a tetrahedral shape.
The groups attached to the oxygen atom are what control the bond angles. Ethers
have the largest boning angles.

4b. Calculate bond lengths (carbon, carbon)

a. Ethane

1.523A
b. Ethylene
1.337A
c. Acetylene
1.212A
d. Benzene
1.420A
e. Cyclohexane
1.523A
Report: List the hydrocarbons in order of bond length from longest to shortest.
1.) Ethane, 1.523 A
1.) Cyclohexane, 1.523 A
2.) Benzene, 1.420 A
3.) Ethylene, 1.337 A
4.) Acetylene, 1.212 A
*Ethane and Cyclohexane have the same bond length.