Consider the following five compounds.

a. CH3CH2CH2CH2CH3

b. OH
'
CH3CH2CH2CH2

c. CH3CH2CH2CH2CH2CH3

d. O
''
CH3CH2CH2CH3

e. CH3
'
CH3CCH3
'
CH3

The boiling points of these five compounds are 9.5 C, 36 C, 69 C, 76 C, and 117 C. Which compound boils at 36 C? Explain.

a. CH3CH2CH2CH2CH3

b. ----->OH
--------->'
CH3CH2CH2CH2

c. CH3CH2CH2CH2CH2CH3

d. ----->O
-------->''
CH3CH2CH2CH3

e. CH3
-->'
CH3CCH3
-->'
-->CH3

I tried to have the bond/double bond connect correctly by using arrows, but that didn't work. I hope you can figure it out.

I cant, but I can offer advice. Arrange the molecules in order of intermolecular bond strength. Look for hydrogen bonding, etc. That will allow you to put the molecules in order of bp.

I can't figure it out either; however, Bob Pursley gave good advice.
First, the lowest b.p. will be those compounds without hyrogen bonding and that means a, c, or e.
The one with the most branching(e) will be the lowest (9.5). a and c are both straight chains; the longest will have the higher b.p.; therefore, a (the 5-C chain) will have b.p. of 36 and c (the 6-C chain) will have b.p. of 69. The alcohol and ketone will have the highest b.p. By the way, I see a 5 valent C atom on b and a 6 valent C atom on d. That's a no-no. I assume b is 2-butanol and I assume d is methyl ethyl ketone but I can't be sure. My tables list a, c, and e b.p. the same as your post; my tables don't list methyl ethyl ketone or 2-butanol at the other b.p. in your post so I may not have them interpreted correctly.

l.hbjl.

To determine which compound boils at 36°C, we need to compare the intermolecular bond strength of the compounds. Higher intermolecular bond strength typically results in a higher boiling point.

From the given compounds, we can identify three main types:
a. CH3CH2CH2CH2CH3 (5-carbon straight chain alkane)
b. CH3CH2CH2CH2OH (4-carbon alcohol)
c. CH3CH2CH2CH2CH2CH3 (6-carbon straight chain alkane)

First, let's consider the presence of hydrogen bonding. Hydrogen bonding occurs when a hydrogen atom is bonded to an electronegative atom (like oxygen, nitrogen, or fluorine) and interacts with another electronegative atom of a nearby molecule.

In compound b, we have the -OH group, which can participate in hydrogen bonding. This increases the intermolecular bond strength and raises the boiling point.

Both compounds a and c are straight-chain alkanes without any hydrogen bonding sites. Straight-chain alkanes have weaker intermolecular forces compared to compounds with hydrogen bonding. Among these, the longer the carbon chain, the stronger the intermolecular forces, leading to a higher boiling point.

Comparing a and c, c has a longer carbon chain, so it will have a higher boiling point than a.

Therefore, the compound that boils at 36°C is a. CH3CH2CH2CH2CH3.