OCT/NOV 2016 EXAM PAPER

My Comments

Section A Answers:

4 1

To determine the formal charge (FC).

See my explanation in exam advice about periodic table and the number of outer electrons
certain elements have in its ground state.

Also, when two elements, A and Q, form a covalent bond A-Q then they share two electrons
and we assign one electron to be around A and one electron of the bond to be around Q.

In a structure if element has same number of electrons around it as in its outer shell at
ground state, then it has a formal charge of zero (0).

In a structure, if an element has more electrons around it as in its outer shell at ground state,
then it has a negative formal charge. If it has one more electron then its formal charge is -1,
if it has two more the FC will be -2.

If in a structure an element has less electrons around it than in its ground state then it will
have a positive formal charge. If it has one less electron then the FC = +1; if it has two more
electrons, then its FC = +2, etc.

5 2

Constitutional isomers: the two structures MUST HAVE the SAME NUMBER OF ATOMS of
particular elements but they ARE CONNECTED DIFFERENTLY in the structures.

6 1 This is a free radical halogenation reaction. The alkane loses a H• and a

carbon radical intermediate is formed. The carbon radical intermediate is the alkane
molecule with a carbon with an unpaired electron (C•).

For the chemical equation:

A review of how to determine the primary, secondary and tertiary C’s:

A primary C (1o C) is attached to one other C atom – the hydrogens attached to a primary C
are called 1o hydrogens. Normally methyl groups have primary C’s and 1o hydrogens. The C’s
that are secondary, 2o, carbons are connected to two other C atoms. The C’s that are tertiary,
3o, carbons are connected to three other C atoms

The alkane in the reaction has the following C’s:

The halogenation reaction of alkanes proceeds via a radical intermediate. Possible radicals
that can form in the reaction are:

The tertiary (3o) carbon radical is the most stable radical and will produce the major
product. This means that the Br becomes attached to tertiary C radical in the molecule to
form the major product:

SECTION B

Question 1 [20]

(a) Draw the Newman projection formulas of the four different conformations of the
compound, CH3CH2CH2Cl, viewing the compound along the C-1 and C-2 bond. Label
each type of conformation accordingly.

(10)
My Commnets: There should be an eclipsed, staggered/ gauche, fully eclipsed and anti- (a
type of staggered) conformations. The Anti is the most stable because the bigger groups are

the furthest from each other and the fully eclipsed is the least stable because the bigger
groups are closest to each other (they are eclipsed – i.e. behind each other)

(b) Give the product and detailed mechanism of the following reaction. Draw the 3-
dimensional representation of the product and provide the IUPAC name according to
the Cahn-Ingold-Prelog rules of the product.
My comments:

NaCN is an ionic compound. All compounds with Na or K are ionic compound where you get
a Na+ ion or a K+ ion and an anion which in this case is CN-.

Any negative ion in a reaction with an alkyl halide can acts as a strong nucleophile and the
reaction goes via an SN2 mechanism – i.e. through a transition state.

The CN- replaces the Br in the structure given.

(c) Draw the structure of any secondary amine and give the IUPAC of the compound.

The above is the structure of N-ethyl-1-butanamine.

My comments:

According to the IUPAC convention, the longest continuous carbon chain has 4 C’s →
but. There is a NH2 group is on C-1 →1-butanamine. There is a 2C chain (not part of the
main chain) attached to N → N-ethyl.

Question 2 [20]

(a) Give the detailed mechanism of the following reaction:

My comments:

What happens when the C=C donates two electrons towards the H+?

The H becomes attached to one of the C atoms that is part of the C=C and the other C (of
C=C) will have appositive charge.
 The primary carbocation is very unstable and will not form

(b) Consider the compound with the proposed name: 1,2-dimethyl-2-chloropent-4-ol-2-

ene.
(i) Draw the structure of the compound that is consistent with the proposed name
given above.
 My comments:

Can you see what is wrong in the structure? The left-hand side C of the C=C has 5
bonds attached to it. C can only have 4 BONDS and possible correct structures
would be:

(ii) Explain what is wrong with the name provided (state each violation of the
IUPAC nomenclature rules and give the correct IUPAC name for the compound.

(5)

What is wrong with the given name: The longest C chain was not given. There are 6 C in the chain
when we include the methyl on C-1 as part of the chain than parent name is hex- and not pent-. The
numbering is from the wrong side of the molecule. This is an alcohol and the numbering should start
at the end that would give the C-OH the lowest possible number: 2-ol. Then the C=C starts at C-3, 3-
en-2-ol should be the end. The change in numbering will change the location of the other
substituent. The substituents in the given name are not listed in alphabetical order. The chloro atom
should be named before the methyl group.

The correct IUPAC name for the compound is thus: 4-chloro-4-methylhex-3-en-2-ol

(c) Use curved arrows to show how bond(s) break and/or form in each process shown
below. Make sure you use the correct Lewis structure in your answer.

(i)

(3)
My comments:

If you look at the structure which has the C=O we see that the C=O became C-O in the
product. This means that the C=O bond broke – it went from a double bond to a single bond.
Also, the structure on the left has the O neutral and, in the product, (RHS of the arrow) O is
negative. Because electrons are negatively charged, this means that in the reaction O got
electrons. So, the C=O bond breaks with the electrons moving to the O.

(ii)

(d) Name the type of bond-breaking that occurs in each of the processes, question 2 (c)
(i) and (ii) of above.

(i) Heterolytic bond-breaking or heterolysis

(ii) Homolytic bond-breaking or homolysis