Organic Chemistry Lab I Final Exam Review

This exam has 37 multiple choice questions and three free response questions. Bring a ruler or straightedge so you can use a nomograph. This exam stresses basic calculations and concepts rather than
memorizing specific compounds or details of procedures. You will be provided with a periodic table, list of
characteristic IR frequencies and NMR shifts, and some equations.
Lab 1: Recrystallization and melting points
How does the second batch of crystals recovered from the mother liquor compare to the first batch
of crystals in a recrystallization?
How does the melting point of a pure compound compare to that of an impure compound?
What happens to the melting point of a pure compound if it still contains residual solvent?
What is the purpose of using a mixed melting point?
Can you do problems 1 - 3 on the lab write-up?
Lab 2 Extraction
How do you determine which is the upper or lower layer in a separatory funnel?
Why is aqueous NaOH used to extract carboxylic acid compounds from organic solvents?
How would you recover the original carboxylic acid after the extraction is complete?
Why is it more effective to extract a compound multiple times with small portions of solvent rather
than once with a large portion of solvent?
Lab 3: Distillation
Can you use the nomograph on page 37? See question 2 on the lab report.
Can you use the phase diagram on page 39? See question 3 on the lab report.
Can you calculate vapor composition using Raoults Law and the solution composition? See
problem 4 on the lab report.
When do you use a fractional distillation instead of a simple distillation?
What is a theoretical plate?
Lab 4: Molecular Modeling
Can you predict which conformers for substituted cyclohexanes are most stable?
Lab 5: Identifying an unknown Carboxylic Acid
Can you calculate the neutralization equivalent and relate it to the MW? You will not be provided
with an equation for this calculation.
What is the relationship between neutralization equivalent and molecular weight?
Have you memorized the three follow-up tests to sodium fusion?
1. What does a black precipitate from Pb2+ indicate?
2. What does a blue color from FeSO 4 /Fe3+ indicate?
3. What does a white, pale yellow or bright yellow precipitate from AgNO 3 indicate?
Lab 6 and 8: Gas Chromatography and TLC
Can you calculate the amount of components based on peak areas?
Can you determine which component is present by interpreting spiked samples?
Which compound exits the GC first, the lowest boiling or highest boiling?
Can you calculate the R f for a TLC?
What is the mobile phase and stationary phase for TLC and GC respectively?

Lab 7: Resolution and Polarimetry

What are racemers and mesomers and can you identify them?
Can you determine the absolute configuration of a chiral carbon (R,S)
Why did you make diasteroemeric salts in this experiment?
What kinds of compounds rotate plane-polarized light?
Can you calculate the percent purity of a sample based on its optical purity? Memorize equation.
Can you do question 1 and 2 on the lab report?
Why did you add K 2 CO 3 (potassium carbonate) to the dichloromethane layer after the extraction?
Lab 9: Spectroscopy
Have you memorized the coupling patterns for proton NMR resulting from adjacent CH n s? For
example, CH 3 -CH 2 -CH 2 O CH 3 would yield in this order a triplet, a multiplet, a triplet, and a
singlet respectively.
Can you calculate the index of hydrogen deficiency? This equation will not be provided.
What happens to an amine, alcohol or carboxylic 1H resonance in the presence of D 2 O?
Can you interpret a 1H NMR spectrum?
Lab 10: Identifying an unknown aldehyde or ketone
Have you memorized the three oxidation tests for aldehydes and ketones?
1. What does a silver mirror with the Tollens test indicate?
2. What does a blue/green color with chromic acid indicate?
3. What does a bright yellow precipitate with the iodoform indicate?
o What are the organic products of each of these reactions?
Lab 11: S N 1 vs S N 2 competing reactions
Have you understood what a substitution reaction is?
Do you know all the differences between SN1 and SN2 reaction? This includes differences in
mechanism, substrates, leaving groups, and solvent effects.
Do you understand the differences in the products from SN1 vs SN2 in regards to stereochemistry?