Organic Chemistry SSG Explanation

Citation for molecule: Johnson, A. L.; Bergman, J. Tetrahedron 2006, 62,

10815-10820.
See notebook paper for drawings
Boiling Point Order (from highest boiling point to lowest): V, III, VI, I, II, IV
Explanation: Boiling point depends on molecular weight, surface area, and
intermolecular forces. Since all these molecules have the same molecular
weight, this does not play a role in the ordering. Molecule V has the highest
predicted boiling point because it has all the carbons in a straight chain.
Therefore, this molecule has the highest surface area to attract to other
molecules. The intermolecular forces are stronger between these molecules
than the others. This means it has the highest boiling point. Molecule III has
the next highest boiling point because it only has one ring of 5 carbons. The
rest of the carbons are in a chain, so this molecule has the next largest
surface area. Molecule VI has the next highest boiling point because 9 of the
carbons are split into three rings, unlike the other molecules not yet
mentioned that have larger rings. This means this molecule has a larger
surface area than the rest of the molecules. This molecule has a lower
boiling point than III because III has a longer chain, so it has a larger surface
area for intermolecular forces. I and II have very similar carbon structures,
so their boiling points are probably fairly similar. I probably has the higher
boiling point because of its double bond between the oxygen and the carbon.
This double bond makes the oxygen more electronegative, so it is more polar.
Molecule IV has the lowest boiling point because it has a ring made up of 9

Organic Chemistry SSG Explanation

carbons. This makes it have a much smaller surface area than the other
molecules. There are less intermolecular forces between these molecules.
Melting Point Order(from highest to lowest): IV, I, II, III, VI, V
Explanation: Molecule IV has the highest melting point because it has one
ring made up of 9 carbons. This single ring is flat, so many molecules can
stack on top of each other. These molecules will have more intermolecular
forces between them, so it will be more difficult to break that structure to
form a liquid. Also, N, OH, and Cl are connected to the chain, and they are
more electronegative and will attract the hydrogens connected to the carbon
ring. This will further connect the molecules together. I has the next highest
melting point because it has two rings, making the structure fairly flat, so the
molecules will have more area to be attracted to each other. I and II are very
similar, so they will have similar melting points, but molecule I has a double
bond with the oxygen, so the oxygen will be more electronegative. This will
lead to stronger intermolecular forces, making the melting point higher.
Therefore, molecule II will have the next highest melting point after molecule
I. Molecule III will have the next highest melting point because it has one 5
carbon ring with the rest of the carbons in a chain. The carbons in the chain
will cause the molecules to not be as compact because the carbon chain will
bend and create spaces between molecules. This will cause a lower melting
point, as the molecules will separate more easily. The next highest melting
point will probably be molecule VI. It has three 3 carbon rings, with carbons
between them to form a chain. This chain can bend even more than

Organic Chemistry SSG Explanation

molecule III, as the chain is longer and there are more rings with less
carbons. This would reduce the intermolecular forces, and the melting point
would be lower. Finally, molecule V would have the lowest melting point
because it has no rings and is a 10 carbon chain. This molecule will bend the
most as it is attracted to other molecules, and this will create spaces
between molecules. The intermolecular forces will not be as strong, so the
melting point
will be the lowest.