Experiment 20

SODIUM BOROHYDRIDE REDUCTION

OF A KETONE
OH

O
1. NaBH4
2. H3O+

Objectives:

To synthesize a tertiary alcohol from a

ketone using a sodium borohydride
reduction.
To purify the product using fractional
distillation.
To analyze the purity of the product using
GC.
To characterize the reactants and
products using NMR and IR spectroscopy.

Before coming to lab

Review these techniques:

Fractional
Vacuum
GC

distillation

filtration

Analysis

REDUCTION USING NaBH4

NaBH4 (sodium borohydride) is a versatile

and useful reducing agent in organic
chemistry.
A reducing agent causes a reaction (a
reduction) in which the product has more
bonds from carbon to hydrogen (or fewer
bond to oxygen)

OH

O
4 R C

R' + 1 NaBH4

4 R C
then H2O

R'

MECHANISM

CH3O
H3C

CH3

CH3

NaBH4

H
(from
NaBH4)

NaBH4 transfers a
hydride ion to the
carbonyl carbon.

CH3O
H3C

CH3H

CH3

CH3OH
H

(from
6M HCl)

The oxygen anion

eventually removes a
proton from water.

H3C

CH3H

CH3

TODAYS REACTION
O

OH

4 (CH3)3CCCH3 + NaBH4

then H2O

4 (CH3)3CCCH3
H

Pinacolone

Pinacolone is reduced using sodium borohydride.

Note that
ketone.

mole of NaBH4 will reduce

moles of

EXPERIMENTAL PROCEDURE
(Synthesis)

Add 3,3-dimethyl-2-butanone and

methanol to 100 mL beaker.
Place in ice water bath.
Add NaBH4 while stirring with glass rod.

100
mL

Continue to react at 0oC for 5min, then

10 min more at RT.
Add 6M HCl dropwise.
Suction filter to remove separate solid
from liquid filtrate.
Transfer to 50 mL round bottom flask.
50
mL

EXPERIMENTAL PROCEDURE
(Purification and GC Analysis)

Set up fractional distillation

apparatus.
Apply heat and collect distillate
below 70oC in a small flask.
Switch to 25 mL round bottom
flask and collect distillate
between 70-85oC.
Cool flask, reweigh.
Prepare GC sample.
to
voltage
regulator

water out

water in

heating
mantle

iron ring

Table 20.1
Theoretical yield (g)

Calculated based on limiting

reactant

Actual yield (g)

Percent yield
Distillation Range (oC)
Product Appearance

(Actual yield/Theoretical yield)

X 100
Give Ti-Tf of distillate
collected in 25 mL round bottom
flask
Give physical state and color of
product

Table 20.2
Calculate based 3,3-dimethyl-2butanone and sodium borohydride ONLY!

Atom Economy (%)

Experimental
Atom Economy (%)
Eproduct
Cost per synthesis ($)
Cost per gram ($/g)

o Review Experiment 13 for calculations!

WASTE MANAGEMENT
o Place the solid boric acid waste from the filtration
into the container labeled SOLID WASTE
located in the waste hood.
o

Place all liquid waste into the container labeled

LIQUID WASTE.

SAFETY CONCERNS

3,3-dimethyl-2-butanone, 3,3dimethyl-2-butanol, methanol and

sodium borohydride are all FLAMMABLE
materials.
Methanol and sodium borohydride are
TOXIC in large concentrations.
Hydrochloric acid is CORROSIVE.