Chemistry 331 - Fall 1996

Exam 1 - Chapters 1 - 3

Answers

1. (15 points) Write a complete IUPAC name for each of the following compounds, including designation of stereochemistry if it is specifically shown:

a)

4-t-butylcyclopentene


b)

trans- or (E)-2-ethyl-3-methyl-1,4-hexadiene


c)

4-bromo-1,1-dimethylcyclohexane


2. (10 points) Examine the pairs of compounds below and identify their relationship to one another. Use the letter codes below:

A - cis-trans isomers
B - conformational isomers
C - resonance forms
D - identical structures
E - none of the above


a)

D


b)

D


c)

E


d)

B


e)

A


3. (10 points) Same as the previous problem set:

A - cis-trans isomers
B - conformational isomers
C - resonance forms
D - identical structures
E - none of the above


a)

D


b)

A


c)

C


d)

B


e)

E


4. (10 points) For the compound shown below:

Write an accurate three-dimensional structure that shows all bonds and their proper orientation.

Write an accurate line structure.


5. (10 points) The pKa values for ethanol (CH3CH2OH) and ammonium ion (NH4+) are 16 and 10, respectively.

Using these compounds and their conjugate bases, write a balanced acid-base equilibrium reaction that would be favorable as written to the right.

CH3CH2OH <====> CH3CH2O- + H+ pKa = 16
weaker acid / stronger base

NH4+ <====> NH3 + H+ pKa = 10
stronger acid / weaker base

NH4+ + CH3CH2O- <====> NH3 + CH3CH2OH
equilibrium favored to the right


6. (15 points) Shown below are incomplete structures. Add the missing substituents to show the proper structure appropriate for the name.

To help you keep organized, the preferred location of the carbon with the methyl substituent is always located with a dot.

trans-1-bromo-4-methylcyclohexane (both chair conformations)


cis-1-bromo-4-methylcyclohexane (both chair conformations)

The structure shown below should correspond to one of your completed structures above.

Is it A, B, C, or D?

C

Write the corresponding Newman diagram for its other chair conformation.

see above


7. (20 points) The addition of HCl to ethene occurs in a two-step mechanism.

Clearly write each of the two steps, including all of the following for each step:

all the bonds in the reactants and the products

the specific bonds that are broken and made

identification of nucleophiles and electrophiles

electron-pushing arrows that show the electron flow

a likely transition state structure

Step 1:

the bonds broken are the C=C pi bond and the H-Cl bond
the new bond made is the C-H bond

Step 2:

no bonds are broken
the new bond made is the C-Cl bond


8. (10 points) Write an approximate reaction energy diagram for the two-step mechanism you wrote in the previous problem. Clearly indicate all of the following on your diagram:

the axis labels

the reactants and products

the transition states

the intermediate

activation energy for each step

H for each step

overall Ea and H

Use the following values for energies (in kcal/mole):

Ea1 = 25, Ea2 = 2, H1 = +20, H2 = -30

overall Ea is the same as Ea1