Chemistry 216

Aldol Worksheet Part B

Instructions:
1. You are to complete the following on your own.
2. Download this word document.
3. Fill in your answers in italic font below the corresponding question. Answers should be
brief and concise. Your responses should be grammatically correct. Be sure to use spell
checker.
4. Your answers should be your own. Plagiarism will result in a zero for the assignment.
5. Worksheets part B are due Friday by 5 pm after the completion of the experiment.

Your Name: Reem Kashlan

1. Create a table below to concisely communicate the important results from your
experiment (this may include important IR peaks, Rf values by TLC, approximate
reaction time, percent yield or anything else that you think is important). Do these
results support your hypothesis? Why or why not.
Aldehyde Percent Yield Rf Values (Aldehyde,
Ketone, & Product)
Aldehyde and
Alkene peaks (cm-1)
4-
Chlorobenzaldehyde
95.6% 0.451, 0.412, 0.373 2858 & 3057
Benzaldehyde 6.62% 0.691, 0.709, 0.582 2818 & 3058
Tolualdehyde 22.57% 0.78, 0.76, 0.53 2732 & NA
Methoxybenzaldehy
de
0% - - - -


The percent yields are the most important set of data obtained throughout the experiment.
They justify our hypothesis that the more electronegative the R group on the aldehyde,
the bigger the percent yield is going to be. The most electronegative R group in the
various aldehydes used was the chlorine which had the highest percent yield of 95.6%,
the next most electronegative R group was the methoxide, however the
methoxybenzaldehyde reaction didnt produce any product due to the contaminated base.
For this reason, the results of the methoxybenzaldehyde results will be ignored. After the
methoxybenzaldehyde the tolualdehyde is the next most electronegative and that reaction
produced 22.6 percent yield. The aldehyde containing the least electronegative R group,
benzaldehyde, produced the least amount of product with about a 6.62 percent yield.
These results support our hypothesis and indicate that the electronegativity of the R
group does affect the success of the experiment. All the Rf values indicate that the ketone
and aldehyde were similar in structure because they have similar Rf values. The product
Rf values are different than the aldehyde and ketone which indicates that the product has
a different polarity than the starting material. However, the product Rf values should've
been the highest but they were the lowest which indicates that there were some impurities
in the product even though the experiment was successful. I know the experiment was


successful because of the IR peaks between the starting aldehyde and the product. All the
starting material contain a peak pertaining to the aldehyde and all the products contain a
alkene peak except the tolualdehyde. The transfer of peaks indicates the success of the
experiment, and the lack of a alkene peak in the tolualdehyde product indicates some
impurities in the product which could have affected the overall results of the experiment.


2. If your initial hypothesis is not supported above, form a new hypothesis and write
it as a single sentence. If your hypothesis was supported, form a new alternative
hypothesis that might support a different interpretation of the data (or alternate
explanation for what you observed) and write it as a single sentence.

As the electronegativity of the R group increases the rate of reaction increases as well.

3. Explain your new hypothesis.

The less electron density present at the carbon at the aldehyde the more reactive the
aldehyde is. Therefore the more electronegative the R group, the more electron
withdrawing it is which relieves the carbonyl carbon from its electron density making it
more readily reactive with the ketone. The more readily the aldehyde reacts with the
ketone the faster the reaction will proceed. The data from the experiment supports this
hypothesis because the chlorobenzaldehyde took under a minute while the tolualdehyde
took 5 minutes and the benzaldhyde took over an hour.

4. Compare the behavior of the different aldehydes (or ketones) that you used in the
Aldol reaction. Did they differ in terms of their solubility in the reaction solvent
(95% ethanol)? Were their corresponding products more difficult to purify? If so,
why? Rationalize your observations in terms of the structural differences of each.

All alternate aldehydes involved in the aldol condensation process behaved similarly to
each other throughout the process of the experiment. All different aldehydes were able to
dissolve in the reaction solvents with equal efficiency. However, during the
recrytallization process the chlorobenzaldehyde product was the easiest and fastest to
purify compared to the tolualdehyde and benzaldehyde products. The benzaldehyde
product was the most difficult to purify. This is probably because the eluting agent used
was ethanol and the more polar the substance the more readily it will dissolve and rid
itself of impurities. The benzaldehyde product has a hydrogen which makes it more
susceptible to difficulties during purification than its polar counterpart,
chlorobenzaldehyde, which has a chlorine.

5. If you had more time to explore the Aldol reaction what would be your objective?
For example, for this experiment our objective was to examine the Aldol reaction
with a series of aldehydes and ketones. Think of a new experimental objective
that could reasonably be explored by a CH216 student and describe it briefly
below. Why would this be interesting and appropriate for CH216?



An alternate objective that could be expanded upon is the rate of reaction. We weren't
able to test the effect of different factors on rate of reaction but that would be beneficial
to the lab and environment if you could make efficient fast experiments that are good for
the environment and produce sufficient yield.



Group Experiment Peer Review

Please rate your group members in the space provided below. Your GSI will use this to
determine GSI points for the lab sessions during this experiment. When you are done fold
the paper in half (writing side in) and turn it in to your GSI. Remember you can change
groups one time per term. Talk to your GSI if you want to find more productive group
members.

Group Member 1 Name:_____________________________________

Rate this group member on their overall contribution to this experiment including
worksheet A preparation and contribution during the lab session (circle one):

0 = didnt contribute 1 = minimal contribution 2 = average contribution
3 = good contribution 4 = outstanding contribution

Briefly explain your rating:




Group Member 2 Name:_____________________________________

Rate this group member on their overall contribution to this experiment including
worksheet A preparation and contribution during the lab session (circle one):

0 = didnt contribute 1 = minimal contribution 2 = average contribution
3 = good contribution 4 = outstanding contribution

Briefly explain your rating:




Group Member 3 Name:_____________________________________

Rate this group member on their overall contribution to this experiment including
worksheet A preparation and contribution during the lab session (circle one):

0 = didnt contribute 1 = minimal contribution 2 = average contribution
3 = good contribution 4 = outstanding contribution

Briefly explain your rating: