Experiment 3

Expt 31B: An Oxidation-Reduction

Scheme: Borneol, Camphor,
Isoborneol

XiaoYing Lu
Date of Experiment: 9 September 2016
CHEM 3522 Friday Lab
Section FQ9
Prof. Gail Horowitz

POST-LAB REPORT
XiaoYing Lu
Lab 3: Camphor
Redn
9/9/2016
Observations:
1. The solution was not cloudy anymore when 0.5 g of granular
anhydrous sodium sulfate was added to it. This is significant because it
indicates that the product isoborneol is successfully isolated from
solution.
2. The white solid was formed after the 0.25 g of sodium borohydride was
added to 0.25 g of camphor along with 1.5 mL methanol. This is
significant because it indicates that the sodium borohydride
successfully reduced the camphor to isoborneol.
Data:
Melting point: 206C - 207C
Preweighed flask = 38.124 g
Preweighed flask + product = 38.312 g
Product weight (isoborneol) = 0.188 g
0.25 g camphor + 0.25 g NaBH4 isoborneol
0.25 g camphor x 152.23 g/ mol = 1.64 x 10^-3 mol
0.25 g NaBH4 x 37.83 g/ mol = 6.60 x 10^-3 mol, so camphor is the limiting
reagent
Theoretical yield of product = 1.64 x 10^-3 mol x 1mol isoborneol

= 0.2533 g
% Yield = (actual yield/theoretical yield) * 100
= (0.188/ 0.2533) * 100 = 74.2 %

Post-lab Question:
1. Interpret the major absorption bands in the infrared spectra of
camphor, borneol, and isoborneol.

The IR spectra for camphor is 1750-1800cm^-1 because of its sharp

peak which indicates the present of its carbonyl functional group C=O
stretching; The IR spectra for borneol and isoborneol is 3200 - 3600
cm^-1 because of its board peak which indicates the reduction of its
carbonyl group and the present of its alcohol O-H stretching
2. Explain why the gem-dimethyl groups appear as separate peaks in the
proton NMR
spectrum of isoborneol while they are an unresolved singlet in borneol.
Gem-dimethyl group refers to two methyl groups of the same carbon atom.

The hydroxyl group of borneol is on the opposite side to the gem-dimethyl

group, so it doesn't matter which methyl group is closer to the OH group; In
Isoborneol, the OH group is on the same side to the gem-dimethyl group,
now its matter which methyl group interacts more with the OH group.
3. A sample of isoborneol prepared by reduction of camphor was analyzed by infrared
spectroscopy and showed a band at 1780 cm-1. This result was unexpected. Why?
If the IR of isoborneol was 1780 cm-1 which is as same as camphor, that indicates the present of
carbonyl group C=O. This is unexpected because isoborneol has no carbonyl group. The present
of carbonyl group means the camphor was not completely reduced to this isoborneol.
4. The observed melting point of camphor is often low. Look up the molal freezing-pointdepression constant K for camphor and calculate the expected depression of the
melting point of a quantity of camphor that contains 0.5 molal impurity. Hint: Look in
a general chemistry book under freezing-point depression or colligative properties
of solution.

Tf = Kf mB; Tf = (39.7 C/molal) (0.5 molal) = 19.85 C.

To- Tf = 19.85,
179 - Tf = 19.85 while the melt point of pure camphor is 179 C; Therefore,
Tf= 159C
5.

The peak assignments are shown on the carbon-13 NMR spectrum of

camphor. Using
these assgnments as a guide, assign as many peaks as possible in the
carbon-13 spectra
of borneol and isoborneol.