Reaction Summary

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Reaction Summary
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Mech
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Mech (for keto to enol trans.)
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Concepts
Chapter 1

• octet rule - writing Lewis structures
• electronegativity trends
• formal charges - computing them
• resonance - drawing structures
• drawing condensed/line formulas
• Brønsted acidity/bascity - trends
• Lewis acidity/basicity

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Chapter 2
1. s versus p bonds 2. hybrids number
angle sp3 4 109.5
sp2 3 120 sp
2 180 3. stereoisomers a.
constitutional isomers b. geometric isomers 4.
intermolecular forces 5. functional groups and
names
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Chapter 3

• 1. Structure of alkanes - staggered, eclipsed,
  gauche,
• Newman diagrams
• 2. Structure of cycloalkanes
• cyclohexane - axial versus equatorial, ring flips
• mono and disubstituted cyclohexanes

Chapter 4

• 1. kinetics
• a. rate constants
• b. activation energies (DG, DH, DS)
• c. rate determining step
• 2. thermodynamics
• a. equilibrium constants
• b. energies (DG, DH, DS)
• c. endothermic/ exothermic

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• 3. linear free energy relationships
• reactivity versus selectivity
• the Hammond principle

• 4. mechanism of halogenation reactions
• a. initiation, propagation, termination events
• b. energetics - how to compute them from BDEs
• c. selectivity - reactivity

5. reactive intermediates a. carbocations,
carbanions, radicals b. stabilities - resonance,
inductive effects c. drawing resonance
structures, allyl, benzyl, etc. d. carbenes
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Chapter 5

• Definitions
• a. chiral/ achiral
• b. diastereomer/ enantiomer
• c. configuration/ conformation
• d. mirror plane/ center of inversion
• 2. Absolute configuration know
  Cahn-Ingold-Prelog rules
• a. determine priority of groups around chiral
  center
• b. determine R, S configuration
• 3. More than one center of chirality
• a. Fischer projections
• i) manipulations, ie inverting, flipping,
  rotating
• ii) determining R, S
• b. Diastereomers - resolution of enantiomers

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Chapter 6
1. Nucleophilic substitution a. mechanisms of
SN1 and SN2 b. rate laws and stereochemistry c
. variation of nucleophile, structure of R group,
solvent and leaving group, L on reaction
rates d. rearrangements in carbocations 2.
Elimination reactions a. mechanisms of E1, E2
and E1cB b. stereochemistry and rate laws c.
orientation - Saytzeff versus Hofmann d. effect
of base, leaving group and alkyl group 3.
Factors favoring substitution versus
elimination
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Chapter 7
1. Know how to calculate elements of
unsaturation. 2. What the p bond in olefins is
and does - relative stability. 3. Nomenclature
cis/trans and E/Z names
Chapter 8

• Markovnikov versus anti-Markovnikov addition
• Syn versus anti addition

Chapter 9
1. Acidity of terminal alkynes
Chapter 10
1. Property of alcohols - lone pairs acidic H
Chapter 11
1. Techniques in multistep synthesis - pp. 489
-492 2. How to figure out reaction mechanisms -
pp. 480 -484