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O
1. NaBH4
2. H3O+
Objectives:
distillation
filtration
Analysis
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)
H3C
CH3H
CH3
TODAYS REACTION
O
OH
4 (CH3)3CCCH3 + NaBH4
then H2O
4 (CH3)3CCCH3
H
Pinacolone
moles of
EXPERIMENTAL PROCEDURE
(Synthesis)
100
mL
EXPERIMENTAL PROCEDURE
(Purification and GC Analysis)
water out
water in
heating
mantle
iron ring
Table 20.1
Theoretical yield (g)
Table 20.2
Calculate based 3,3-dimethyl-2butanone and sodium borohydride ONLY!
Experimental
Atom Economy (%)
Eproduct
Cost per synthesis ($)
Cost per gram ($/g)
WASTE MANAGEMENT
o Place the solid boric acid waste from the filtration
into the container labeled SOLID WASTE
located in the waste hood.
o
SAFETY CONCERNS