Key

Name: ___________________________________________________________ Period: _________

Lecture 50
Introduction to Organic Reaction Mechanisms with Acids and Bases
Student Notes

Learning Objective(s)
• Distinguish between Bronsted-Lowry acid-base reaction mechanism and Lewis acid-base reaction mechanisms
• Determine the structure of the products of an acid-base reaction given the curved arrow mechanism
• Draw curved arrow mechanisms for acid-base reactions given the products of the reaction.

Inorganic vs Organic Acids and Bases

The acids we have learned about previously were mostly inorganic acids: HCl,
H2SO4 and HF.

organic
Acids that contain carbon in their structure are called _____________
acids
__________and donate ______________.
just like inorganic acids, they ___________ protons
Carboxylic acids are the most common organic acids. Acetic acid (CH3COOH),
the active ingredient in vinegar, is a weak organic acid.

protons Organic bases may involve a variety of different

accept ___________.
A base is a species that is able to ____________
structures, but they must all share the common feature of having electron pairs that are able to accept protons. The

pale
electron pairs could be ________ ________ electrons
pair _________________on a neutral or negatively charged species or
it electron
__________________________. Organic bases are in line with the Lewis definition of bases as electron pair donors.

•In OH-, the electron pair is a lone pair of electrons

on a negatively charged species

•In methanol, the electron pair is a lone pair of

electrons on a neutral species
•In ethene, the electron pair is the π electron

For the functional groups containing oxygen atoms: carbonyl group C=O, alcohol R-OH, and ether R-O-R, the
electrons on
love pair _________________
________________ _______________ ______________to
oxugerin these groups are able to be donated
accept ____________________,
the protons so functional groups like aldehyde, ketone, alcohol and ether are all
organic bases
_______________________or Lewis __________.
___________ bases

· O
Often, lone pairs are omitted from
structural formulas.
o
Draw the lone pairs on the oxygen
· · atoms in each of the following
structures shown on the left.
 Organic Reaction Mechanisms
electron transfer
A reaction mechanism is the step-by-step ________________ process
______________ ______________that converts reactants
curved ____________are
to products. ___________ arrows used to illustrate the reaction mechanism. Curved arrows should
always start at
_____________________ _________ electrons and end in the spot that is receiving the electrons.
the _______________,

within a ______________to
Note: Curved arrows are often also used to show how electrons move ______________ molecule form
structures
resonance _________________.
_________________
Remember, resonance structures would always be represented with a double headed arrow and the arrows will
show the movement of electrons within the molecule!

carbocation is a carbon with a _____________

2nd Note: a ____________________ formal ____________.
positive ____________ charge

As previously mentioned, the electrons in a π bond can be

donated so the curved arrow in a mechanism can also begin
from a double or triple bond

Recall that Lewis acid-base reactions involve an

Recall that Bronsted Lowry acid-base reactions involves a electron
_______________ ________ donor
pair __________(base) and
proton __________and
____________ donor proton
a ___________ electron
_______________ ________ acceptor
pair ________________(acid).
acceptor
_______________. In the reaction mechanism for a
...
Bronsted-Lowry acid base reaction, the curved arrow
end with_____________(H).
should ____________ a proton
F I
-
H

G
= B- E:
:..
-

* ⑦
:
H -- +: The mechanism above represents a Lewis acid base
reaction (electron pair donor and electron pair
it acceptor)

Note: All Bronsted-Lowry acid base reactions are

The mechanism above would represent a Bronsted-Lowry
also Lewis acid base reactions but not all Lewis acid-
acid base reaction because the base is accepting a proton.
base reactions are also Bronsted-Lowry acid-base
reactions. The mechanism above cannot also be a
It is also a Lewis acid-base reaction because the base no
Bronsted-Lowry reaction because there is _____
donates an electron pair in order to accept the proton.
transfer
proton_______________.
___________
For each of the following reaction mechanisms:

1. Draw the product structure. Include non-zero formal charges in your product structure

2. Determine if the mechanism represents a Bronsted-Lowry acid-base reaction or a Lewis acid-base reaction

3. Label the acid and the base on the reactant side

-N-0
:
⑦

-
⑦ -
-
+:
0

o
: ②

-H
Il Il
:
5-8
.

H-0-
+
Hz(-4p -

H
!
-

0:

-- +
Il
-
H

:
0
Il

H 13- -j
,+
Hin -

#-
H30 -
- CH3
I
H
 O
Il
:
C-
-- = CH3
Asc i
+ CH3-CH2-8. -
H

=
-
I
⑦ : 0
-

:
-B-
-
:

Gi
:

-
- ↓ : + - In-
10

I
I
H

Hoc/-OCH
Hs)
① + H- H
-

-
CEC :
i

X
I

H -
c
-

H +

it
 1
LI ①
⑪ NHz

F
H
↓
I
C-
Hyd - n =

↑ I

Boron must attach to CH3

this carbon to avoid 5 bonds
on the other carbon
For each of the following reaction mechanisms:

1. Determine if the mechanism represents a Bronsted-Lowry acid-base reaction or a Lewis acid-base reaction

2. Add the curved arrows that would accomplish the transformation

3. Label the acid and the base on the reactant side

↑
1

M
 -

&

ta