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Alison Nguyen

Partner: Nancy Lee


7/24/17
1. Title- Lab 9 Sodium Borohydride reduction of a chiral ketone

2. Purpose- The purpose of this lab is to use sodium borohydride to reduce the ketone of 2-
methylcyclohexanone to an alcohol.

3. Reactions-
Reduction of 2-Methyl-cyclohexanone

4. Mechanisms-

5. Reagent Table-

2-Methyl- Sodium Methanol Sodium Dichloromethane 2-Methyl-


cyclohexanone Borohydride Hydroxide cyclohexanol
(3M)
MW 112.17 37.83 32.04 40.0 84.93 114.19
(g/mol)
Mp (C) -- 300 -98 -- -97 --
Bp (C) 162-163 -- 64.7 -- 40 --
Density 0.92 -- 0.79 -- 1.33 --
(g/mL)
Grams 0.3 0.053 -- -- -- 0.305
mL 0.326 -- 1.25 1.25 1.0 --
Mol 0.00267 0.001401 -- -- -- 0.00267
equiv 2 1 -- -- -- 2
Chem 273L manual & Pubchem
Alison Nguyen
Partner: Nancy Lee
7/24/17
6. Experimental-
1.25 mL of methanol in reaction tube
add 0.33 mL of 2-methyl-cyclohexane
cooled in ice bath and mix with agitation
250 mL beaker with water on hot plate
once methanol solution cooled, 0.053 g of NaBH4 added in three portions in one
minute intervalssolution began to bubble vigorously
solution was cooled until vigorous bubbling slowed down
reaction removed from ice bath and cooled to RT for 10 minutes
boiling stick placed into rxn tube and mixture boiled on water bath until half the
volume remained, tube cooled to RT
1.2 mL of 3M NaOH added to the reaction tube
1 mL of water added to tube, solution became cloudy
clear upper layer formed
aqueous layer (bottom) removed and transferred to separate tube
extraction was done with 0.5 mL of 1:5 dichloromethane hexanes (repeated once
more)
bottom layer was removed (organic) and placed into first reaction tube
first test tube washed with 1 mL of water and aqueous layer removed (2x)
1 mL of brine added to organic layer and agitated two layers formed
organic layer removed and placed into third reaction tube, dried with sodium sulfate
liquid removed and placed into pre-weighed tube
little sample taken and TLC analysis done with 1:5 DCM hexanes solvent (drawn
below)

DCM removed by boiling


Flask weighed with product and IR reading of product taken

7. Data-

Mass of 10 mL flask: 16.394 g


Mass of flask with product: 16.425 g

Mass of product 0.031 g


Alison Nguyen
Partner: Nancy Lee
7/24/17

8. Results-
Reduction of 2-Methyl-cyclohexanone

0.326 mL x 0.92 g/mL = 0.00267 moles of 2-Methyl-cyclohexanone


112.17 g/mol

0.053 g = 0.001401 moles of Sodium Borohydride


37.83 g/mol

Limiting Reagent: 2-Methyl-cyclohexanone


*Sodium Borohydride has 4 protons that can continuously react therefore is not limiting
reagent

Theoretical Yield:
0.00267 moles x 114.19 g/mol = 0.305 g of 2-Methyl-cyclohexanol

Percent Yield:
0.031g x 100 = 10.2%
0.305 g

9. Discussion-

Sodium Borohydride is an important reagent in organic chemistry because it is used to


reduce aldehydes and ketones to alcohols. In this experiment, 2-methyl-cyclohexanone was
reduced by sodium borohydride to produce 2-methyl-cyclohexanol. Due to the chiral center
in the 2-methyl-cyclohexanone, the product contains 2 diastereomers with different physical
properties. The limiting reagent in this reaction was the 2-methyl-cyclohexanone. Although
the molar amount of sodium borohydride used was less, sodium borohydride has 4 hydrides
that can react with several molecules of the ketone, therefore it cannot be considered the
limiting reagent in the reaction.
The percent of this yield was 10.2%. Possible reasons for this low yield is due to an
experimental error. Instead of adding only dichloromethane and doing subsequent
extractions, 1:5 DCM hexanes solvent was used instead. The use of the wrong reagent may
have affected the retrieval of the layers that were supposed to be extracted and as a result,
less product was recovered. The IR spectrum displays a broad, strong signal at around 3355,
indicating the presence of an OH group. (Figure 1) This is an indication that the reaction
went through successfully since the product is an alcohol. Theoretically, there should have
been two spots that were close in value on the TLC plate, however, only one spot was seen.
This is due to the fact that the diastereomers have Rf values that are very close in proximity,
therefore it is likely that they overlapped when they eluted.
Alison Nguyen
Partner: Nancy Lee
7/24/17

10. Post-Lab Questions


1)

2) The conformer where the methyl group is equatorial is preferred over the conformer
with the axial methyl group due to van der waals repulsions. In the axial position, the
methyl group encounters repulsions with other axial hydrogens. The molecule with
the axial methyl requires more energy to be formed, therefore the conformer with the
equatorial methyl is preferred since it does not encounter these repulsions.
3)

4) The product which is preferred in this reaction is the 2-Methyl-cyclohexanol where


the alcohol and the methyl groups are in a trans configuration. This diastereomer is
preferred because when the nucleophile attacks the position with the carbonyl carbon
from the top face of the molecule there is less stearic hindrance than if the
nucleophile were to come in from the bottom. The nucleophile therefore attacks the
carbon from the top face, giving the trans product in the reaction.