Chemistry 212
Fall 2010
Carbonyl Reactions - 9
Mechanisms for Substitution for an -Atom group in Carbonyl Compounds: (continued)
j.
O
O
f.
CH3
C
NH2
+
H3O
+
-> WHAT OVERALL CHANGE OCCURS (Bonds made and
broken)? Illustrate on the given structures.
CH3
->
+
C
H
O
+
NH4
WHERE ARE THE HIGHEST ENERGY ELECTRONS?
Circle on original structures.
-> HOW CAN THE HIGHEST ENERGY ELECTRONS BE USED IN A SIMPLE REACTION STEP TO BEGIN THE CONVERSION
OF THE REACTANTS TOWARD THE PRODUCTS? Propose a reaction step with original structures using arrows. Write
intermediate product structures below:
-> NOW WHERE ARE THE HIGHEST ENERGY ELECTRONS? Circle on your new structures.
-> HOW CAN THESE HIGHEST ENERGY ELECTRONS BE USED IN A SIMPLE REACTION STEP TO MAKE AND BREAK
BONDS THAT WILL MOVE THE INTERMEDIATE STRUCTURES TOWARD THE PRODUCTS? Propose a reaction step with
your new structures using arrows. Write next intermediate product structures below:
Continue until you have reached the products.
Carbonyl Reactions-9
2
Reflector’s Report Discussion:
Identify the most important concepts you learned from this activity:
What questions remain?
Strategy Analyst’s Report Discussion:
We had considerable discussion about identifying the HEE in reaction f. Using grammatically correct English sentences, present the final claim
as to the tow possible sites for initial HEE and a warrant supporting the choice of the HEE used for the first reaction step.
3
Carbonyl Reactions-9
Out of Class Applications for Carbonyl reactions-9
A. Read: CGWW
pp. 277-291, 292-294 & 723-735
B. Try to apply your mechanism(s) to example p of substitutions for carbonyl oxygen introduced in Carbonyl Rxns-1 and reproduced below.
p.
O
O
H3 O +
H +
OH
+ H2 O
O
O
-> WHAT OVERALL CHANGE OCCURS?
->
WHERE ARE THE HIGHEST ENERGY ELECTRONS?
-> WHAT CAN THE HIGHEST ENERGY ELECTRONS DO TO AID IN THE NEEDED BOND MAKING AND BREAKING?
-> NOW WHERE ARE THE HIGHEST ENERGY ELECTRONS?
-> WHAT CAN THEY DO TO AID IN THE NEEDED BOND MAKING AND BREAKING?
Continue until you have reached the products.
C. Text Applications:
Appropriate Questions:
CGWW
P. 302-: Problems
2, 4 & 6