Organic Chemistry I


Adjust your thinking here to embrace the



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Adjust your thinking here to embrace the
broader scope
of acids and bases in an organic chemistry
context.
Here, we will take the reaction between acetone and H
+
as an example, to understand the reaction deeply by
exploring the
reaction mechanism,
and learn how to use the curved arrows to show it.
A reaction mechanism
is the step-by-step electron transfer process that converts reactants to products.
Curved arrows
are used to illustrate the reaction mechanism. Curved arrows should always start at the
electrons, and end in the spot that is receiving the electrons. The curved arrows used here are similar to those
for resonance structures (
section 1.4
), but are not exactly same though. Please note that in resonance
structures, the curved arrows are used to show how the electrons are transferred
within
the molecule, leading
to another resonance structure. For mechanism purposes, there must be arrows that connect
between
species.
3.2 Organic Acids and Bases and Organic Reaction Mechanism | 89


Notes for the above mechanism:

For the acid-base reaction between C=O group and the proton, the arrow starts from the
electron pair on O, and points to the H
+
that is receiving the electron pair. A new O-H bond is
formed as a result of this electron pair movement.

In this acid-base reaction, ketone is protonated by H
+
, so this reaction can also be called the

protonation of ketone
”.

The product of the protonation is called an “oxonium ion”, which is stabilized with another
resonance structure, carbocation.

Alkene (C=C): Although there are no lone pair electrons in the C=C bond of alkene, the π electrons of
the C=C double bond are able to accept proton and act as base. For example:
Example: Organic acid and base reaction
Predict and draw the products of following reaction and use curved arrow to show the mechanism.

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