9. Stereochemistry. Based on McMurry’s Organic Chemistry , 6 th edition. Stereochemistry. Some objects are not the same as their mirror images (technically, they have no plane of symmetry) A right-hand glove is different than a left-hand glove (See Figure 9.1)
McMurry’s Organic Chemistry, 6th edition
on a chirality center converts it to its
Only sp3 hybridized C atoms can
be chirality centers.
physical properties except for the
direction in which they rotate
the plane of polarized light.
A single enantiomer is said to be optically active.
Cholesterol has eight chirality centers
Morphine has five (9.17)
Reaction between two optically inactive (achiral) partners that produces a product with a center of chirality, always
leads to an optically inactive
product – either racemic or meso.
If you start out with optically inactive reactants, you will end up with optically inactive products.
Draw detailed mechanism and
consider stereochemistry of
addition of Br2 to cis and trans
As a general rule, reaction of a chiral reactant with an achiral reactant which introduces a new center of chirality, leads to unequal amounts of the distereometric products. If the chiral reactant is optically active theproduct will also be optically active.
Problem 9.23 What products are
formed from reaction of HBr
27-30, 32-34, 36-43, 45, 46,
48-50, 52, 53, 57, 59, 65-67, 73
Owl for Chapt 9 Nov 18
Test on Chapter 9 Nov 20