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Exam 4 Review

The document is a review guide for Exam 4, covering topics such as conjugation, heat of hydrogenation, resonance, and stability of benzene. It discusses the differences between stereoisomers and conformers, as well as the Diels-Alder reaction and its rules. Key concepts include the effects of conjugation on acidity (lower pKa), bond lengths, and the stability of reaction intermediates and products.

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52 views79 pages

Exam 4 Review

The document is a review guide for Exam 4, covering topics such as conjugation, heat of hydrogenation, resonance, and stability of benzene. It discusses the differences between stereoisomers and conformers, as well as the Diels-Alder reaction and its rules. Key concepts include the effects of conjugation on acidity (lower pKa), bond lengths, and the stability of reaction intermediates and products.

Uploaded by

cade.b.brink
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Exam 4 Review

Ben Ivins
Conjugation
Conjugation vs. Isolation
Conjugated vs. Isolated
Heat of Hydrogenation
Remember, Conjugated systems are more stable = Lower starting energy
MO Theory for basic conjugation (1,3 Dienes and
carbocations)
Overlapping P-Orbitals lead to delocalization of electrons.
Common Resonance Forms
Effect of Conjugation on PKA
Know the Trends!!!!

● Resonance makes the conjugate base more stable = easier to lose a


hydrogen = More Acidic = LOWER PKA!!
● Resonance = LOWER PKA
Stability of Benzene
Bond Lengths
● More S Character = Shorter Bond Length!!!
○ SP3>SP2>SP
Resonance on Carbonyls
Pay Attention to Resonance Structures
Conjugated Dienes
Remember Definitions of Stereoisomers vs Conformers

● Stereoisomers must break a bond to interconvert


● Conformers interconvert freely

Pay attention to Cis vs Trans Alkenes (Z or E),

When Rotating around a single bond you can form the S-Trans or S-Cis
Conformation of a diene
Conjugated Dienes
E/Z vs Cis/Trans
● Cis and Trans are only used to classify alkenes when they have two
substituents, on opposite sides of the alkene.
● E and Z can be used when there are one or more substituents on
opposite sides that are different
○ Highest priority substituents on the same side = Z
○ Highest Priority substituents on opposite sides = E
1,2 vs 1,4 addition to 1,3 Dienes
2 things to think about:
● Which is the most stable intermediate?
○ Substitution of carbocation

● Which is the most stable product


○ Substitution of Alkene
Notes:
Think about an Energy Diagram:

● Kinetic Product has a lower


activation energy, and therefore
dominates at a lower temperature
● Thermodynamic Product is overall
more stable, but has a higher
activation energy and therefore will
dominate at a higher temperature
Other Notes about 1,2 vs 1,4 addition
1,2 isn’t always kinetic, and 1,4 isn’t always thermodynamic:

● Pay attention to specific molecules! You should be able to reason your


way through based off of stability of intermediates and stability of final
products
Diels Alder Reactions!!
Electron Withdrawing Groups
How to draw the product of a Diels-Alder Reaction:
How to Draw the reactants of a Diels alder Reaction
● Find the single alkene
bond and number the
carbons
● Remember it is a 4 + 2
addition
Rules:
● Diene must be in the S - Cis Conformation
Endo vs. Exo
Endo is Favored!
Cyclopentadiene dimer
● Cyclopentadiene (what you will use in 353 to perform a diels alder
reaction) is very reactive with itself. Results in an Endo dimer. Can be
separated with heat.
Diels Alder Practice:
Other Chapter 12 Practice Problems:
Chapter 10 Review
Things to Remember
What is the PKA
of an Alkyne?
Remember the synthesis of Disparlure
Chapter 11
Ozonolysis
What does Zn or (CH3SCH3) do?

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