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by JA MES
in OR G AN IC CH E MIS TRY 1 , OR G AN IC RE AC TIO N S
The previous four posts on acidbase, substitution, addition, and elimination covered
the 4 main reactions in organic chemistry I. Now its time
to go beyond those mainstays to introduce a few of the
less common (but still important) reactions you learn in
organic chemistry 1. They will be rearrangements,
radical substitution, and cleavage (oxidative cleavage).
Lets look at rearrangements in this post. As with
everything in this series, the point is not to
understand why just yet, but to be able to see from the
diagrams what bonds are broken and formed. You need
to understand how to read line diagrams. But other than
that no further skills are required. The point here is to be
able to follow the plot to see what is happening. A
later series of posts will go into more detail as
to why things happen, but it takes time to build up that
knowledge.
Rearrangement reactions are really interesting. They
can accompany many of the reactions weve previously
covered such as substitution, addition, and elimination
reactions. In fact, if you dont look closely, sometimes
you can miss the fact that a rearrangement reaction has
occurred. Lets look at a substitution reaction first.
in AL CO H OL S , A LK YL HA LI DE S , O R GA NI C C HE MI S TRY 1 , O R GA NI C R EA C TI O NS
The big question is, whats going on? How did this
happen?
As it turns out, reactions that go through
carbocations can sometimes undergo
rearrangements. And looking back at substitution
reactions, recall that theSN1 reaction goes through a
carbocation intermediate. In this post well go through
when youll expect to see a rearrangement reaction.
Lets think back to carbocations. Theyre carbon atoms
with six electrons bearing a positive charge. In other
words, theyre electron deficient 2 electrons short of a
full octet. So it would make sense that carbocations
become more stable as you increase the number of
electron donating groups attached to them. Alkyl
groups are a perfect example. Thats why carbocation
stability increases as you go from primary to secondary
to tertiary.
in OR G AN IC CH E MIS TRY 1
Molecular Rearrangement
https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/Questions/Rearang/rng
prb1.htm
Six reactions in which molecular rearrangement takes place are shown below. Formulas and some
other information about the products are provided. Draw a structural formula for each of the
designated products.
To draw a formula use the Drawing Window on the right below. Do not draw hydrogen atoms, and
do not attempt to indicate stereochemical configurations. When you are finished, check your answer
by pressing the appropriate Check Product button.