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Exam 4 review: Ch.8
GO TO SLIDESHARE POWERED BY LINKEDIN AND SEARCH
“DANIELEISENSTEIN1”
Alkene fun facts
 C=C bond
 Sp2 hybridized = trigonal planar
 Pi and sigma bond
 Don’t conform
Alkene Stability
Practice
Leaving Group Ability
Nucleophilicity (correction)
 Increases with negative charge
 Increases as steric hinderance decreases
 The following slide shows the periodic trend
Beta carbons
 Beta carbons are around the functional group
 Finding beta carbons is the first step
 Find Beta carbons and draw all Elimination products
 This is 8.1 in solution manual
Its all about that base!
 Basicity increases as it gets negative
 Basicity is not as dependent on steric hinderance as
nucleophiles
 A sterically hindered base is called a nonnucleophilic base
 B: is the symbol for a base
Trend for basicity
Elimination reaction
 Forms alkene
 We need a strong base
 We need a Leaving Group
 As number of R groups increase, rate of
reaction increases
This Photo by Unknown Author is licensed under CC BY-SA-NC
E2 reaction
 Rate= k[substrate][base]
 Bimolecular
 Concerted
 Strong base
 Mechanism
 Requires anti periplanar geometry
 Trans-diaxial on a ring
This Photo by Unknown Author is licensed under
CC BY-SA-NC
Practice
practice
practice
Major vs. Minor products
 We want the most stable product
 Follows Zaitsev’s rule
 The less stable product can be favored
 Hoffmann product
 Due to steric effects
This Photo by Unknown Author is licensed under CC BY-SA-NC
Practice (8.12)
What alkenes are
formed?
Follow zaittsev rule
E1 reaction
 Weak base
 Unimolecular
 Involves carbocation intermediate
 Two-step reaction
 Rate= k[substrate]
 Mechanism
This Photo by Unknown Author is licensed under CC BY-NC
E1 vs. E2
E1 vs. E2 vs. Sn1 vs. Sn2
 BIG DADDY FLOW CHART
 This is not mine
 This is the work of clutchprep
 If you are having trouble in this
course or in organic chemistry 2, I
highly recommend them
This Photo by Unknown Author is licensed under CC BY-NC-ND
Practice (8.16)
Questions I like
 8.1, 8.3, 8.5, 8.6, 8.7, 8.8, 8.9, 8.10, 8.11, 8.12, 8.13, 8.14, 8.15, 8.18, 8.19
 You know what, I Iike all of them

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Chapter 8 exam 4 review

  • 1. Exam 4 review: Ch.8 GO TO SLIDESHARE POWERED BY LINKEDIN AND SEARCH “DANIELEISENSTEIN1”
  • 2. Alkene fun facts  C=C bond  Sp2 hybridized = trigonal planar  Pi and sigma bond  Don’t conform
  • 6. Nucleophilicity (correction)  Increases with negative charge  Increases as steric hinderance decreases  The following slide shows the periodic trend
  • 7.
  • 8. Beta carbons  Beta carbons are around the functional group  Finding beta carbons is the first step  Find Beta carbons and draw all Elimination products  This is 8.1 in solution manual
  • 9. Its all about that base!  Basicity increases as it gets negative  Basicity is not as dependent on steric hinderance as nucleophiles  A sterically hindered base is called a nonnucleophilic base  B: is the symbol for a base
  • 11. Elimination reaction  Forms alkene  We need a strong base  We need a Leaving Group  As number of R groups increase, rate of reaction increases This Photo by Unknown Author is licensed under CC BY-SA-NC
  • 12. E2 reaction  Rate= k[substrate][base]  Bimolecular  Concerted  Strong base  Mechanism  Requires anti periplanar geometry  Trans-diaxial on a ring This Photo by Unknown Author is licensed under CC BY-SA-NC
  • 16. Major vs. Minor products  We want the most stable product  Follows Zaitsev’s rule  The less stable product can be favored  Hoffmann product  Due to steric effects This Photo by Unknown Author is licensed under CC BY-SA-NC
  • 17. Practice (8.12) What alkenes are formed? Follow zaittsev rule
  • 18. E1 reaction  Weak base  Unimolecular  Involves carbocation intermediate  Two-step reaction  Rate= k[substrate]  Mechanism This Photo by Unknown Author is licensed under CC BY-NC
  • 20. E1 vs. E2 vs. Sn1 vs. Sn2  BIG DADDY FLOW CHART  This is not mine  This is the work of clutchprep  If you are having trouble in this course or in organic chemistry 2, I highly recommend them This Photo by Unknown Author is licensed under CC BY-NC-ND
  • 22. Questions I like  8.1, 8.3, 8.5, 8.6, 8.7, 8.8, 8.9, 8.10, 8.11, 8.12, 8.13, 8.14, 8.15, 8.18, 8.19  You know what, I Iike all of them

Editor's Notes

  1. Can you confirm if the gem-disubstituted alkene is
  2. Make sure to take out before I go into next semester
  3. In powerpoint there is DBN and DBU. Do we need to teach this?