Test 2
Dr. Bachrach
CHEM 2319-2
3/5/2008

1) Provide the IUPAC name for the following compounds.

2) Provide the appropriate reagent(s) to affect the following reactions.

a)

b)

3) Sketch the energy vs. reaction coordinate diagram for the reaction of 1‑butene with HCl. Make sure to indicate the structure of all reactants, intermediates and products. Draw a (*) at the position of any transition states.

Keep in mind that the H⁺ can add to ether C1 or C2, leading to two different intermediate a primary cation and a secondary cation. The diagram above accounts for both pathways!

4) The hydrogenation of compound A gives two diastereomeric products. Identify the products, indicate which is the major one, and explain you answer.

The addition of the hydrogens is cis but that leads to a methyl group and a saturated C4 atom – both of which are achiral sites. So how do we get two different products? The hydrogens can add from either face of the double bond. Keep in mind that the t-butyl wants to be in the equatorial position always, and locks the ring, keeping it from ring flipping. The hydrogen atoms can then be delivered from the top or bottom as shown below.

This gives us two products – the cis- and trans-1-t-butyl-4-methylcyclohexanes. The trans isomer is more stable because both substituents are in the more energetically favorable equatorial positions. The trans isomer is therefore the major product!

5) Predict the product(s) of the following reactions

a)

b)

c)

d)

6) Draw the structure of (4S)-4-ethyl-4-methylcyclooctyne

7) Starting with ethyne, any alkyl halide you like and any inorganic reagents, propose a synthesis of the following compound.