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1 Give the final product of the following reaction. Give your answer as a text answer. If more than one species is correct, put your answers in alphabetical order. HNO3 H2SO4 A B C D E F G Q1 H
2 Give the final product of the following reaction. Give your answer as a text answer. If more than one species is correct, put your answers in alphabetical order. HNO3 H2SO4 A B C D E F G Q1 H
3 Exam 1 Time: Tuesday, September 20: 7:00 9:00PM OR Wednesday, September 21: 7:00 9:00PM OR Thursday, September 22: 7:00 10:00PM Location Soc/Anthro Testing Center Chapters will be covered in this order: Chapter 11, 14, 15, 19, 13 Practice Exams are Posted B A Practice Exam 1A B B Practice Exam 1B Deadline for alternate arrangements is Monday, 9/19/2016 at 4:30 PM (i.e., close of business) An oral make-up exam will be required for making up the exam for all students not taking the exam on the above dates or having already made prior arrangements
4 Order of Coverage (Exam 1) Homework Assignment Due Date 1 B IR Functional Groups (wdeadline) Tuesday, August 23 2 B Mass Spec - Molecular Ion (wdeadline) Wednesday, August 24 3 B Mass Spec - Isotope Effects (wdeadline) Thursday, August 25 4 B Number of Peaks 1H NMR Spectra (wdeadline) Friday, August 26 5 B Number of Peaks 13C NMR (wdeadline) Saturday, August 27 6 B Theoretical NMR Chemical Shift (wdeadline) Sunday, August 28 7 B Theoretical NMR Integration (wdeadline) Monday, August 29 8 B Theor. NMR Spin-Spin Splitting (wdeadline) Tuesday, August 30 9 B NMR Spectroscopy Problems (wdeadline) Wednesday, August B C NMR Structure ID (wdeadline) Thursday, September 1 11 B A Nomenclature Alkyl Halides (wdeadline) Friday, September 2 12 B B Alkyl Halide Nomenclature (wdeadline) Saturday, September 3 13 B A Halogenation of Alkanes (wdeadline) Sunday, September 4 14 B B Halogenation of Alkanes (wdeadline) Monday, September 5
5 Order of Coverage (Exam 1) Homework Assignment Due Date 15 B A Oxidation and Anti-oxidants (wdeadline) Tuesday, September 6 16 B Aromaticity (wdeadline) Wednesday, September 7 17 B B Arene Nomenclature (wdeadline) Thursday, September 8 18 B A Halogenation of Arenes (wdeadline) Friday, September 9 19 B B Halogenation of Arenes (wdeadline) Friday, September 9 20 B A Arene Rxns Inorganic Acids (wdeadline) Saturday, September B B Arene Rxns Inorganic Acids (wdeadline) Saturday, September B A Friedel-Crafts (wdeadline) Sunday, September B B Friedel-Crafts (wdeadline) Sunday, September B Arene Mechanistic Issues (wdeadline) Wednesday, September B B Arene Mechanisms (wdeadline) Wednesday, September B A Nucleophilic Aromatic Subs (wdeadline) Thursday, September B B Nucleophilic Aromatic Subs (wdeadline) Friday, September 14 Exam 1 September 20, 21, 22
6 Regiochemistry of the Halogenation Cl2 FeCl3 FeCl4 -
7 Regiochemistry of the Halogenation Cl2 FeCl3 FeCl4 -
8 Regiochemistry of the Halogenation Cl2 FeCl3 FeCl4 - The circled groups are more stable than the other resonance structures.
9 Regiochemistry of the Halogenation Cl 2 FeCl 3 FeCl 4 - Groups that stabilize a carbocation lead to o,p-direction
10 Regiochemistry of the Halogenation Cl2 FeCl3 FeCl4 -
11 Regiochemistry of the Halogenation Cl2 FeCl3 FeCl4 - The circled groups are less stable than the other resonance structures.
12 Regiochemistry of the Halogenation Cl 2 FeCl 3 FeCl 4 - Groups that destabilize a carbocation lead to m-direction
13 Regiochemistry Ortho, Para-Directors Groups that stabilize a carbocation Usually alkyl groups Meta-Directors Groups that destabilize a carbocation RC=O, CN
14 Cl2 FeCl3 FeCl4 -
15 Cl 2 FeCl 3 FeCl 4-4 Resonance Structures are better than 3 Resonance Structures!
16 Regiochemistry Ortho, Para-Directors Groups that stabilize a carbocation Usually alkyl groups Groups with lone pair electrons O N Meta-Directors Groups that destabilize a carbocation RC=O, CN
17 Steric Hindrance Issues Para > Ortho Para > Ortho Para = Ortho No steric hindrance to approach at paraposition while there is steric hindrance to approach at the ortho-position. No steric hindrance to approach at paraposition while there is steric hindrance to approach at the ortho-position. No steric hindrance to approach at paraposition while there is only a little steric hindrance to approach at the ortho-position.
18 Activated vs Deactivated Reference Activated Deactivated Reacts faster Less needed Reacts slower More needed
19 Activated vs Deactivated Reference Activated Deactivated Reacts faster Less needed Cl 2 or Br 2 Reacts slower More needed Reacts at room temperature without catalyst Need FeX 3, Need FeX 3, Need FeX 3,
20 Halogens Electronegativity Destabilizes carbocations π-electron Resonance Stabilizes carbocations
21 Halogens Electronegativity Destabilizes carbocations π-electron Resonance Stabilizes carbocations In general, resonance beats electronegativity Halogens are o,p-directing, but are deactivated
22 Regiochemistry Ortho, Para-Directors Groups that stabilize a carbocation Usually alkyl groups Groups with lone pair electrons O N Halogen Meta-Directors Groups that destabilize a carbocation RC=O, CN
23 Oxygen vs Nitrogen Oxygen Does not bond well to acids (H + ) or catalysts Activated and always o,pdirecting Nitrogen Bonds well and fast to acids (H+) or catalysts Acids meta-directing No acids o,p-directing
24 Regiochemistry Ortho, Para-Directors Groups that stabilize a carbocation Usually alkyl groups Groups with lone pair electrons O N (NOT in acid (H + ) or with a catalyst) Halogen Meta-Directors Groups that destabilize a carbocation RC=O, CN N with acid (H + ) or a catalyst
25 Which of the following resonance structures are correct for the p- bromination of aniline? A B C D E F Q2
26 Which of the following resonance structures are correct for the p- bromination of aniline? A B C D E F Q2
27 Give the next major organic intermediate(s) of the following reaction. Br 2 FeBr Q3 A B C D E F
28 Give the next major organic intermediate(s) of the following reaction. Br 2 FeBr Q3 A B C D E F
29 Give the major product(s) of the following reaction. A HNO 3 H 2 SO 4 B Q4 E. There is no reaction or the correct product is not listed here. C D
30 Give the major product(s) of the following reaction. A HNO 3 H 2 SO 4 B Q4 E. There is no reaction or the correct product is not listed here. C D
Give the major product(s) of the following reaction.
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