Challenge Problems 3

1. An sp hybrid orbital is made up of one s orbital and one p orbital, so this means that is
has 50% s character and 50% p character. The sp2 hybrid orbital has, 33.3% s
character and 66.7% p character, while the sp3 hybrid orbital has 25% s character and
75% p character. Electrons exhibit maximum tendency to stay close to the nucleus, due
to the fact that the nucleus contains protons which gives it a positive charge, and
electrons are negatively charged which causes an attraction between the two. With this,
we can determine that that the greater the s-character in a hybrid orbital, the greater the
tendency of the electrons to stay close to the nucleus. This means that an sp hybridized
carbon holds electrons closer in comparison to sp3 hybridized carbons. A Lewis acid is
an electron acceptor; therefore, the central atom should be able to keep electrons closer
for it to be considered more acidic. In conclusion, a C atom with sp hybridization exhibits
greatest acidic character compared to a C atom with sp2 or sp3 hybridization.

2.

3. The reason these two similar reactions have different equilibrium constants has
something to do with its entropy. The first reaction has two reactions to produce two
products however the second reaction was able to produce two products from one
reactant. There is an increase in entropy in the second reaction which in turn causes to
the

reaction to favor the products. This explains why the Keq of the second reaction is larger
than the first.

4. Quinuclidine is more basic and nucleophilic than triethylamine even though the Nitrogen
atoms in the compounds are both surrounded by 3 R groups. This is due to the fact that
there is lesser steric hinderance in quinuclidine than in triethylamine. The cause of lesser
 steric hinderance in quinuclidine is that the surrounding alkyl groups are tucked back
and Nitrogen is more exposed, which means that it can easily donate its lone pair
electrons, in comparison to triethylamine where its alkyl groups has access to free
rotation which may then obstruct an incoming electrophile.

5.

6. The compound J contains three chlorine atoms. The reaction happens in the presence of
methanol as a nucleophile. The carbon atom bearing chlorine atom is directly attached
to highly electronegative oxygen atom. The first step of reaction involves nucleophilic
attack of methanol on carbon atom bearing chlorine atom. The next step involves
deprotonation of oxygen atom by removal of proton. The mechanism is shown below: