Solution for Problem set 2
1. Provide the missing organic product for the following reaction. Indicate the major
product when more than one product possible.
2. Provide the necessary reagents for each reaction shown below
3. Starting from 1-Butyne, any alkyl halide and reagent needed outline the synthesis of
a) Hexane b) 2-Methyl-3-hexene
4. Give the product expected from the hydroboration-oxidation of each of the following
alkenes.
a) Cyclohexene b) trans-4-methyl-2-pentene c) 2-methyl-2-pentene
5. Alkene X of unknown structure gives the following products after treatment with ozone
followed by aqueous H2O2. What is the structure of X?
6. Propose a structure for the unknown compound given the following data:
7. What alkene of molecular formula C7H14, when treated with ozone followed by zinc and
acetic acid will give propanal and 2-methylpropanal.
8. Starting from acetylene and any alkyl halide needed, synthesize
a) 2-Chlorobutane b) 4-Methyl-2-pentanol
9. Predict whether each of the following substitution reaction is likely to be SN1 or SN2:
Product a) would occur via SN1 mechanism, because the chlorine is substituted on a
benzylic carbon and so the reaction path passes via stable benzylic carbocation. On theother
hand the initial compound is secondary halide and the phenyl group is a bulky groups that
blocks the backside attack, this favors SN1 in preferance to SN2.
However product b) would favor through SN2 mechanism, because the initial material is
primary bromide and so the incoming nucleophile has a greater chance to attack the back
side of the carbon holding bromine.
10. Tell whether each of the following reactions is likely to be SN1, SN2, El, or E2 and
predict the product of each.
11. Predict the major alkene product of the following E1 reaction and show the mechanism.
12. How can you explain the fact that trans-1-bromo-2-methylcyclohexane yields the non-
Zaitsev elimination product 3-methylcyclohexane on treatment with base?
It is generally known that, a base peak up the proton which is aligned anti and periplanar
to the leaving groups (usually halide) for E2 reaction mechanism, and the proton which is
expected to give Zaitsev elimination product is aligned syn which is not the right
stereochemistry for E2 reaction mechanism. This is why non-Zaitsev elimination product
was furnished.
13. Explain why each alkyl halide stereoisomer gives a different alkene in the E2 reaction
mechanism shown below.
The first reaction compound gave the highly substituted double bond product via E2,
because the proton at the ring junction is anti and periplanar to bromine that made the
right chemistry for incoming base to pick up the proton on the carbon adjacent to the
carbon holding bromine, whereas carbon-carbon double bond is formed and carbon-
bromine bond was broken via single and concerted step.
However, in the second compound the proton on the junction which is expected to give
Zaitsev E2 product is aligned syn, which is not the right chemistry for E2 mechanism.
Due to this the base prefers to pick up the terminal proton which is aligned ant and
periplanar to the bromine to establish non-Zaitsev elimination product.