Week 4 problem set

1. The IR assignment for this quarter is due on Friday, April 25, 2008 at 5 pm in YH3077E. No late assignments will be accepted.

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1. A student acquires a GC spectrum for his final product from the reduction reaction.

Solvent: dichloromethane, Column: HP-5, l = 30 m, 0.25 mm, Temperature: T(initial)= 100 ^oC, T(final)= 180 ^oC, t = 4 min

Results:

Time (min)	Height (pA)	halfwidth (min)	Peak
1.40	20000	0.30	A
3.55	200	0.18	B
3.65	1200	0.30	C
3.75	200	0.15	D

a. Which peak belongs to which compound in the final product? How can he confirm these assignments?

b. Determine the percentage composition in terms of isoborneol and borneol in the final product that all three compounds have the same response factor.

c. How would the spectrum change if the run would be started at T(initial)=80 ^oC and ends at T(final)=200 ^oC with a run time of 6 min?

d. What would change (if anything) if the flow rate would be increased?

2. Review extraction theory (Survival Kit Reader, Mohrig, etc )and then take the Online Quiz

http://bacher.chem.ucla.edu/TakeQuiz/?id=c51ce410c124a10e0db5e4b97fc2af39

In order to take the quiz, you have to go through a UCLA ICP address. This means that you either have to use your Bruin-Online account or go through the VPN (Vitual Private Network, software can be found here: http://www.bol.ucla.edu/services/vpn/) to have this UCLA ICP address.

To log in, use your last name and your student ID. If you are experiencing problems, contact the instructor via email and include your full name (indicated which one is your last name), your student ID, section and TA. (Hint: Think very careful about each response since many of the questions have more than one answer to them!) Even though you can take the quiz until one hour prior to meeting 4 of your section, you should not delay taking it since there might be some problems with the server or the login. Also, there seem to be problems with MAC systems and Safari Browser. The best is using IE 7.0 or Firefox. After you submit the answers, your score should appear on your screen. If this does not happen, you will have to retake the quiz. (There will not be any possibility to retake the quiz weeks later!). The quiz is worth 10 points.

3. Referring to the phase transfer reaction carried out in the lab, answer the following questions.

a. What is the function of (NBu₄)(HSO₄) in his reaction? Could it be replaced with (NBu₄)Br?

b. What is the function of NaOCl in the reaction?

c. Why is it important that the reaction mixture is stirred vigorously?

d. The reaction mixture is extracted using sodium bicarbonate and water. Rationalize these steps.

e. A student decides to use ethanol as solvent for the column chromatography step. Which problem does this pose?

f. Why does benzil crystallized before benzoin during the recrystallization step?

g. The final product exhibits a fairly low carbonyl stretching mode. Explain briefly why.

PART II. (Reduction of Camphor, In-lab assignment)

This assignment is to be completed in the UCLA Science Learning Center computing labs during the lab period (or afterwards if you don't complete it in the allotted time). The assignment is due during meeting 5 and is worth 10 points.

Determine the dipole moment for borneol, camphor and isoborneol. (see below instructions). In the GC spectrum, camphor has the shortest retention time, then isoborneol and borneol last. Can you rationalize the GC results based on the calculated dipole moments of these compounds? (Note: The GC column is relatively non-polar.) Do not apply any constraints in this part!