Quiz 1

1. Sketch the 2px and 2py orbitals (around the same nucleus, please).

2.

a. Write the electron configuration of carbon.

b. Are the p electrons in the same orbital? Why or why not?

3. What element is represented by the following ground state electron

configuration?

1s22s22p63s23p63d2

4. Answer the following questions about NH3 (ammonia):

a. What type of bond is formed between nitrogen and hydrogen?

b. Draw a Lewis structure for ammonia.

c. What shape is the smallest unit of ammonia? (Name the shape and draw a
structure.)
 Quiz 2
Draw reasonable Lewis structures for the following:

1. CO2

2. (CO3)2-
 Quiz 3
1. Draw reasonable Lewis structures for the compound below:

CSHCl

2. Calculate the formal charges of each atom except for hydrogen in these
compounds:

a.

b.
 Quiz 4
1. Draw two more resonance contributors. Label the major and minor
resonance contributors.

2. Draw as many resonance contributors as you can for:

3. Write the condensed forumla for:

4. Write the line angel forumla for:

Quiz 5
1. Which is the stronger acid, HF or HBr (EN of F = 4.0, EN of Br = 3.0)?

2. Place the following compounds in order of increasing acidity (1=least acidic,

5=most acidic).

3. In the following reaction leavel each reactant as a Lewis acid or a Lewis base and
provide curved arrows to indicate bond making and bond breaking (i.e., provide the
mechanism). Be sure to indicate all movements of electrons with curved arrows.

4. Does the following equilibrium lie to the left or the right?

Quiz 6
1. Indicate the hybridization of all atoms except hydrogen in the compounds
below.

a.

b.

2. Draw the resonance contributor(s) for the structure below. Label the
major and minor contributor. Indicate the hybridization of all atoms except
hydrogen.

Quiz 7
1. Draw as many structural isomers as possible for C5H11Br.

2. Label the molecules below as polar (P) or nonpolar (N).

Electronegativities:

C - 2.5
F - 4.0
H - 2.2
Cl - 3.2
Al - 1.6
 Quiz 8
1. Place the molecules below in order of increasing boiling point (1=lowest,
6=highest).

2. Give the IUPAC name for the compound below.

a.

b. (CH3)2CH(CH2)3CH(CH3)2
 Quiz 9
1. Draw the least stable conformation of pentane using a Newman projection of
the view along the C2-C3 bond.

2. Using the table of strain energies below, arrange the conformations of 2-

methylbutane in order of increasing stability (1=least stable, 3=most stable).
What is the difference in energy between the most stable and the least stable
confotmation?

Strain energies:
H-H eclipsing = 1 kcal/mol
CH3-H eclipsing = 1.3 kcal/mol
CH3-CH3 eclipsing = 3.0 kcal/mol
CH3-CH3 gauche = 0.9 kcal/mol
 Quiz 10
1. Draw the two chair conformations of trans-1-t-butyl-3-
methylcyclohexane. Circle the more stable conformation.

2. Draw the two chair conformations of trans-1-t-butyl-4-

methylcyclohexane. Circle the more stable conformation.

3. Which isomer is more stable? Why?

 Quiz 11
1. For each of the following reactions, calculate ∆ H0 and label as exothermic or
endothermic.

a)

b)

2. a) An industrial synthesis of diethyl ether involves the high temperature, acid

catalyzed condensation of two ethanol molecules. This process is shown below.
Draw all of the transition states and label the intermediates (I, II, III, etc.).

b) Assuming that this process is exothermic overall, and that step 2 is the rate
determining step and step 1 is faster than step 3, draw an enerygy profile for this
process.
 Quiz 12
1. Place the following compounds in order of increasing bond dissociation energy
for the indicated bond (1=lowest BDE, 3=highest BDE).

2. Place the following radicals in order of increasing stability (1=least, 4=most

stable).

Quiz 13
1. Place the following carbocations in order of increasing stability (1=least, 3=most
stable).

2. Place the following carbanions in order of increasing stability (1=least, 4=most

stable).

3. Label each of the following pairs of compounds as identical, structural isomers,

enantiomers, or diastereomers.
 Quiz 14
1. Provide an IUPAC name for the following compound.

2. Label each of the following pairs as identical, structural isomers, conformational

isomers, enantiomers or diastereomers.
 Quiz 15
Label each of the following pairs as identical, structural isomers,
conformational isomers, enantiomers or diastereomers.

a)

b)

c)
 Quiz 16
1. Give a detailed mechanism for the following solvolysis reaction. Show the
movement of all electron pairs with curved arrows and show all formal charges. Be
sure to account for the stereochemistry of each product.

2.Give the organic products of the following reactions:

a)

b)

c)
 Quiz 17
State whether Reaction A or Reaction B has the faster rate. If both reactions have the
same rate, place SAME in the box.
 Quiz 18
Give the major product of each of the following reactions. Be sure to indicate
the proper stereochemistry when appropriate.

1.

2.

3.

4.
5.

Quiz 19
1. The reaction below presently falls in the "Hey! I have never seen this before!
No Fair!" category.Using what you DO know about electrophiles and
nucleophiles and other important species, please provide a mechanism that
explains the formation of each product. Remember to use curved arrows to
properly indicate electron flow and to show all formal charges.

2. From the Fall 2001 Exam: From cyclohexane and any inorganic reagents,
synthesize the compound below.
 Quiz 20
1. Give the compound below an acceptable IUPAC name.

2. Place the following alkenes in increasing order of stability (1=least, 4=most stable).

3. Label the compounds below as stable or unstable.

4.

5.
 Quiz 21
1.

2.

3.
 Quiz 22
1.

2.

3.
 Quiz 23
1.

2.

3.

4.

5.
6. Explain the formation of each product of the following reaction with a
mechanism.
Use curved arrows to indicate electron flow, and show all intermediates
and formal charges.

Quiz 24
1.

2.

3.

4.

5. Synthesize the following compound from alkanes of no more than two

carbons, any peroxyacids, and any inorganic reagents.

6.

7.

8.

9.

10. Synthesize the following compound from alkanes of no more than two
carbons and any peroxyacids and inorganic reagents. Pay attention to
stereochemistry.
 Quiz 25
1.

2.

3.

4. Synthesize the compound below from alkanes of three carbons or less,

any aldehydes or ketones of three carbons or less, and any inorganic
reagents.

5. Provide a mechanism to explain the formation of the two products in the

reaction below. Be sure to indicate the movement of all electrons with
curved arrows, to show all intermediates and to show all formal charges.
 Quiz 26
1.

2.

3.

4.
 Quiz 27
1.

2.

3.

4.
5. Synthesize the compound below from alcohols of two carbons or less, any
oxidizing or reducingagents, any peroxyacids, and any inorganic reagents.

6. Synthesize the compound below from cyclohexane, any alkanes of two

carbons or less, any oxidizing or reducing agents, any peroxyacids, or any
inorganic reagents.
 Quiz 28
All protons in the same magnetic environment are referred to as an equivalent set of protons. Each equivalent set
produces a signal in the 1H NMR spectrum. Label each equivalent set of protons (a, b, etc.) in the compounds below.
Circle the set that would appear most downfield in the 1H NMR of each compound.

A.

B.

C.

D.

E.

Determine the number of nonequivalent sets of protons and label each set (a, b, etc.). Predict the multiplicity of each
signal (i. e., how many peaks is each signal split into) for each set of protons in the 1H NMR of each compound.

A.
B.

C.

D.

E.
Quiz 29