Professional Documents
Culture Documents
Brandon Conley
Harvard Extension School
October 2, 2017
(Online/Virtual)
Tuesdays 4-5 pm EST (Zoom)
2. scant heavy
cream, chopped
cilantro
Dinner
Organic Synthesis
Learning Reactions
• Focus first on a functional group. Can it act as a donor? With what orbitals?
Can it act as an acceptor? With what orbitals? Am I comfortable generalizing
this functional group in the context of larger structures?
H
Learning Reactions
• Focus next on transformations. What other functional groups can we prepare
starting from this functional group? Do we know any relevant oxidation and
reduction chemistry involving this functional group? Which mechanisms are
important for me to understand?
Learning Reactions
The Reaction Spreadsheet/Table/Chart
H+ cat.
Draw the starting materials and reagents necessary for preparation of each
of the compounds shown below.
5
O H+ cat. 1 O4 6
2 6
HO OH
4 2 O 7
1 3 5 7 3
Numbering carbons
is essential here!
What relevance do these have to learning how to solve organic synthesis
problems?
IDK
Provide the most appropriate reagent/conditions for accomplishing the
chemical transformation pictured below. No more than two steps will be
necessary. Briefly justify your decision.
O OH
MeO MeO
O O
OH O
HO H
Main issue: extent of reaction (how far do we want the reaction to go?)
Provide the most appropriate reagent/conditions for accomplishing the
chemical transformation pictured below. No more than four steps will be
necessary. Briefly justify your decision.
O Ph OH
Main issue: order of operations (will earlier reactions influence the course of
subsequent reactions?)
Aside: More Adventures in Selectivity with Conjugated Carbonyls
Reduction:
1. LiAlH4, Et2O
2. H+ workup
not
reliable;
just don't
Organometallic Additions:
1. RLi, Et2O
2. H+ workup
HO R
Recap: what relevance do these have to learning how to solve organic
synthesis problems?
Benadryl, a much older antihistamine, essentially “carpet-bombs” many types of receptors all over the
body indiscriminately, including in the CNS, which is why it has such a high incidence of side effects like
drowsiness, dry mouth, dry eye, etc. It is very nonselective. On the other hand, Zyrtec was designed to
be much more targeted and selective, which is why we don’t see patients experiencing the stereotypical
antihistamine side-effect profile on newer agents like Zyrtec and Allegra, which are more selective for
their receptor subtype.
The point is that whenever we can, we want to use selective and targeted reagents in preference to
perhaps stronger but nonselective ones!
Solving Organic Synthesis
Problems: Setup
Propose a reasonable synthetic pathway from the indicated starting materials to
the desired product below. You should need no more than seven synthetic steps
to complete this synthesis.
O Br Cl
H
Starting Materials
OH
Desired Product
Solving Organic Synthesis
Problems: Execution
Propose a reasonable synthetic pathway from the indicated starting materials to
the desired product below. You should need no more than seven synthetic steps
to complete this synthesis.
O Br Cl
H
Starting Materials
OH
Desired Product
Solving Organic Synthesis
Problems: Try This at Home!
Propose a reasonable synthetic pathway from the indicated starting materials to
the desired product below. You should need no more than five synthetic steps to
complete this synthesis.
OH
Br
Starting Materials
Mg
Br MgBr
Et2O
(making an organolithium would
also work perfectly well)
Desired Product
Supplement Slide*: Title Slide
Graphic
In case you’re wondering, the 3D molecule pictured on the title slide is a model
of camphor, a natural product with a characteristic fragrance.
*Content on Supplement Slides will not be tested explicitly on exams; however, it may help you gain a better
understanding of content that will be tested!