Organic Chemistry I
Maryam Fardpour
Write structural formulas for all the products
that would be obtained when each of the
following alkyl halides is heated with
sodium ethoxide in ethanol.
Give the products that would be formed
when each of the following alcohols is
subjected to acid-catalyzed dehydration.
 Acid-catalyzed
dehydration of either 2-methyl-1-butanol
or 3-methyl-1-butanol gives 2-methyl-2-butene as the
major product. Write plausible mechanisms that explain
these results.
Give the IUPAC names for each of the
following:
Starting with 1-methylcyclohexene and using
any other needed reagents, outline a
synthesis of the following deuterium-labeled
compound:

We notice that the deuterium atoms are cis to each other, and
we conclude, therefore, that we need to choose a method that
will cause a syn addition of deuterium. One way would be to use
D2 and a metal catalyst.
Outline a synthesis of phenylethyne
from each of the following
 Write
a three-dimensional representation
for the transition state structure leading to
formation of 2-methyl-2-butene from
reaction of 2-bromo-2-methylbutane with
sodium ethoxide.