C HEMISTRY   261:     O RGANIC   C HEMISTRY   I,   S PRING   2015
Section  001:  MWF  11:15-­‐12:05  in  Cp211
Section  002:  MWF  2:30-­‐3:20  in  Cp  201
Text:
Instructor:  Dr.  Jen  Krumper
Organic  Chemistry  (Bruice,  7 th   ed.)
Course  webpage:   sakai.unc.edu
Prerequisite:  a  grade  of  C-­‐  or  better  in  102
Other  Materials:  i>Clicker  brand  clicker  (required;  use  any  clicker  made  by  this  company),  subscription  to
ALEKS  (required;  available  online),  subscription  to  Mastering  Chemistry  (required;  available  online  or   bundled  with  your  text),  HGS  model  kit  (required),  student  solutions  manual  (optional).
C ONTACT   I NFORMATION   .    To  promote  personal  connection  and  efficiency  in  communication,  I  generally   refrain  from  corresponding  with  students  by  email.    Instead,  I  provide  many  opportunities  for  in-­‐person
conversation  (see  below).    Use  email  ( jkrumper@unc.edu
)  only  in  emergency  situations.
Questions  about  science:
M  8:30-­‐9:00  (drop  in  help  with  Dr.  K.:  Kenan  C143)
M  6:30-­‐7:30  (Q&A  session  with  Lan-­‐Anh  &  Martin:   TBD )
Tu  12:30-­‐1:30  (Q&A  session  with  Dr.  K.:  Kenan  C143)
Tu  6:30-­‐7:30  (Q&A  session  with  Ellen  &  Olivia:   TBD )
W  9:00-­‐9:30  (drop  in  help  with  Dr.  K.:  Kenan  C143)
W  3:00-­‐4:00  (Q&A  session  with  Daniel,  Sarah  &  Missy:   TBD )
Th  2:00-­‐3:00  (Q&A  session  with  Dr.  K.:   TBD )
Questions  about  logistics,  course  success  strategies,  or  just  to  say  hello:     Kenan  C147F
T U   2:30   –   3:00     Th  10:30   –   11:00   F  3:30-­‐4:00
If  you  wish  to  discuss  an   exam ,  bring:  1)  the  exam  you  wish  to  discuss,  2)  your  notes  +  practice  problems,  and
3)  a  completed  post-­‐exam  reflection  survey  (available  under  “Help  and  Extra  Resources”  on  sakai).
C OURSE   D ESCRIPTION
Chemistry  261  is  the  first  half  of  a  two  semester,   cumulative  overview  of  organic  chemistry.    We  will   cover  the  fundamental  tools  of  organic  chemistry  and  apply  these  to  the  reactions  of  alkanes,  alkenes,   alkynes,  alkyl  halides,  ethers,  and  alcohols.
You   may   find   this   course   unusual   for   a   science   class,   and   surprisingly   similar   to   acquiring   a   second   language.    You  will  only  be  asked  to  perform  simple  mathematical  operations,  but  you  will  learn  many   reagents   (nouns)   and   to   develop   a   feel   for   the   mechanisms   (verbs)   by   which   these   reagents   act.
Later,  you  will  approach  multi-­‐step  chemical  synthesis,  which  is  analogous  to  sentence  construction.
Becoming  fluent  in  the  language  of  organic  chemistry  requires  deep  learning  and  long-­‐term  retention   of  what  you’ve  learned.    This  can  be  achieved   only  by  working  a  wide  variety  of   practice  problems .    As   such,  expect  success  to  require   at  least  10  hours  per  week   of  intensive  practice  outside  of  class.
T HE   C HEMISTRY   261   C OMMUNITY
Our  class  emphasizes   teamwork  and  good  sportsmanship.    Grading  is  on  a  flat  scale,  not  a  curve.    In
Chemistry  261,  ultra-­‐competitive  behavior  is  not  only  unattractive;  it  is  also  unnecessary.
A CADEMIC   H ONESTY
Cheating   is   NOT   a   part   of   the   Chemistry   261   culture,   nor   does   it   benefit   the   cheater.     Academic   dishonesty  carries  heavy  consequences  ( http://instrument.unc.edu/instrument.text.html#IPreamble ).
All  students  know  what  it  means  to  cheat  on  an  exam,  and  you  all  know  how  to  NOT  do  this.      We  will
do  a  lot  of  collaborative  work  in  this  class,  however,  and  other  assignments  may  not  be  as  clear.    If  you   are  unsure  whether  a  task  is  intended  to  be  individual  or  group  work,  just  ASK!

C HEMISTRY   261  IS  AN   E NGAGED -­‐L EARNING   C LASS
You,  the  student,  are  the  master  of  your  own  destiny:  how  well  you  learn  in  every  class  depends   largely  on  your  choices:  do  you  engage  with  the  material  every  day,  or  do  you  cram  for  exams?    Do  you   think  deeply  about  what  you’re  learning,  or  do  you  skate  on  the  surface?    Do  you  have  the  courage  to
ask  for  help  when  you  need  it?    Do  you  help  others  when  they  ask?
To  succeed,  you  will  need  to   make  good  choices  and   work  hard .    To  support  you  this,  we  will  be   explicit  about  which  activities  best  support  learning,  and  we  will  reward  the  activities  with  class  points.
We  call  these   Daily  Work  Points ,  and  they  make  up  15%  of  your  grade.
To  earn  Daily  Work  Points,  you  will  prepare  for  each  class  period  with  a   pre-­‐class  assignment :  video   lectures,  an  ALEKS  activity,  and/or  selected  textbook  readings.  We  will  then  delve  into  more   challenging  skills  and  topics  with  in-­‐class   quizzes ,  discussions,  and   group  work .     Chemistry  261
mentors  and  I  will  rove  during  these  activities  help  you  build  these  skills  in  the  right  way.    After  class,   you  will  reinforce  your  skills  by  doing  textbook  problems  in  a  well-­‐organized   notebook .  Each  part  of   this  class  structure  has  been  shown  to  improve  success  in  chemistry.
D AILY   W ORK    AND   A TTENDANCE
Your  overall  Daily  Work  score  is   roughly  50%  based  on  in-­‐class  work.    Excellent  attendance  is  required.
While  you  may  not  earn  a  score  higher  than  100%  on  Daily  Work,  more  Daily  Work  points  will  be  offered   than  are  necessary  to  earn  a  100%  (see  Daily  Work  grading  chart  below).    This  means  it  will  be  relatively   easy  to  make  up  points  lost  by  a  missed  class  or  two.
ALEKS :
Course  Code  =  KGMH4-­‐TUXX9
We  will  use  an  online  learning  system  called   ALEKS   for  the  first  few  weeks  of  the  semester.    ALEKS  is   quite   different   from   other   online   homework   systems:   it   assesses   your   current   knowledge   state   and   assigns  specific  tasks  catered  to  you.    Your  experience  in  ALEKS  will  be  unique:  no  two  students  will   have  exactly  the  same  set  of  learning  tasks.    Work  individually  in  ALEKS.    The  program  is  designed  such   that  collaboration  of  any  kind  will  create  a  significant  amount  of   extra  work  for  you.  More  information   is  available  on  sakai.
P RE -­‐C LASS   A SSIGNMENTS
Video  lectures,  ALEKS  Objectives,  and/or  reading  will  be  assigned  prior  to  each  class.    The  content  in   these   Pre-­‐Class  Assignments  is  required:  it  will  be  tested  on  exams.    Typically,  however,  it  will  not  be   re-­‐presented  in  lecture-­‐format  in  class.    Instead,  we  will  use  class  time  to  expand  the  foundations  laid   by  this  preparatory  work.
C LICKER   Q UIZZES
You  will  be  given  a  short  individual  clicker  quiz  at  the  start  of  each  class  on  that  day’s   Pre-­‐Class
Assignment .  No  makeups  will  be  given.    (See  notes  on  Daily  Work  and  Attendance  above.)    You  may   use  notes  you  have  taken  on  the  Pre-­‐Class  Assignment  on  the  quiz,  but  no  other  materials.
C LICKER   A CTIVITIES
Throughout   class   period   we   will   learn   new   concepts   and   skills   in   lecture,   then   apply   these   to   real   organic  chemistry  problems.    You  will   work  together  with  a  team  to  master  these  tasks.    You  may  use   your  book  and  other  notes  to  work  the  problems.

M ASTERING C HEMISTRY :   C OURSE   C ODE     =   MCKRUMPER60422
Online   Self-­‐Tests  will  be  assigned  in  MasteringChemistry  at  the  end  of  each  chapter.    Self-­‐Test   problems  are  much  like  end-­‐of-­‐chapter  problems  from  the  textbook.    You  will  receive   five   submissions   per  question  and  the  entire  self  test  will  take   90  minutes .     Nota  bene :  in  order  to  earn  credit  for  your   work,  you  must  click  the  “give  up”  button  on  multi-­‐part  problems  where  you  do  not  achieve  the
correct  answer.
No  late  work  will  be  accepted  in  MasteringChemistry  for  any  reason.    The  MasteringChemistry  clock   will  be  used  to  determine  the  submission  date/time.    This  clock  may  differ  from  yours,  so  submit  your   work  well  in  advance.       You  may  use  your  book  or  other  resources,  but  all  MasteringChemistry   assignments  are  to  be  worked  independently.     Any  collaboration  or  discussion  of  MasteringChemistry   assignments  will  be  treated  as  a  violation  of  the  UNC  Honor  Code .
S URVEYS
You  will  complete  a  variety  of  polls  and  surveys  on  sakai  during  the  class.    These  will  help  you  get  to   know  your  colleagues,  will  prompt  you  to  assess  what  works  and  what  doesn’t  in  your  study  habits,   and  will  help  me  reflect  on  how  the  class  is  going.    These  surveys  and  a  few  others  administered  over   the  course  of  the  semester  will  be  worth  a  few  Daily  Work  Points.
E XAMS  AND   F INAL
See  schedule  for  dates  of  midterm  exams.   Unless  you  have  a  valid  medical,  emergency,  or  university   sanctioned  excuse,  a  missed  exam  will  be  scored  as  a  zero .   Such  excused  absences  must  be  validated   with  appropriate   documentation  and  alternative  arrangements  will  be  made .
If  you  know  will  need  to   miss   an   exam   in   advance   (e.g.   for   a   medical   procedure   or   University   field   trip),   you   may   arrange   to
take  the  exam  early.    Arrangements  must  be  made  at  least  two  weeks  in  advance.
G RADING
Item
Daily  Work  (more   info  below)
Midterms
Final  Exam
Total
Grade  Breakdown
Points  Possible
Daily  Work  %  score  is   scaled  to  75  points
300
(3  scores:  100  pts  each)
125
500
%  of  Grade
15%
60%
(3  scores:    20%  each)
25%
100%
Grade  thresholds  may  be  scaled  down  at  the  instructor’s  discretion,  but   guaranteed  minimum
Percentage   score   values  are  listed  below.  (e.g.  a  score  of  68%  is  guaranteed  a  C-­‐)
Course   grade
93.0  –  100   A
Percentage   score
Course   grade
87.0  –  89.9   B+
Percentage   score
75.0  –  79.9
Course   grade
C+
Percentage   score
60.0-­‐66.9
Course   grade
90.0  –  92.9   A-­‐
83.0  –  86.9   B
80.0  –  82.9   B-­‐
70.0  –  74.9   C
67.0  –  69.9   C-­‐
<  60.0
D
F

D AILY   W ORK   G RADING
Your  Daily  Work  %  score  will  be  calculated  as  a  %  of   275  Daily  Work  points.
More  than   300  points  of  Daily  Work  will  be  available,  but  your  score  may  not  exceed  100%.
Item
ALEKS  work
Points  ea.
60
Number
1
Min.  total  pts.
60
Clicker  Quizzes  (every  class  period)
Clicker  Group  Activities  (every  class  period)
Post  Exam  Reflection  Surveys  +  Other  Surveys
Mastering  Chemistry
3
2
2-­‐5
80
>  30
>  30
>  3
1
90
60
10
80
Minimum  Daily  Work  Points  Available       300
Maximum  Daily  Work  Points  Applicable  to  Final  %  score         275
H OW  TO   S UCCEED  IN   O RGANIC   C HEMISTRY
Be  a  good  class  citizen.
Smile  at  your  classmates  and  introduce  yourself  to  them.    Ask  someone  how   their  day  is  going.  Switch  off  all  electronic  devices  (phones,  computers,  etc.)  while  in  class.
Print   up   the   list   of   recommended   practice   problems   and   mark   your   progress   on   it.     Keep   a   spiral
notebook  for  your  practice  problems.
Do   some   organic   chemistry   every   day.
Complete   all   the   Pre-­‐Class   Assignments   before   coming   to   class.    Complete  all  the  recommended  practice  problems  in  your  notebook.    Stay  on  top  of  your  ALEKS   work  and  MasteringChemistry  Self  Tests.
A  good  study  session  feels  like  a  hard  workout;  expect  to  be  tired  afterwards.
Be  well  rested  when
you  start  studying  and  study  with  focus  +  determination.
Hand  write  the  majority  of  your  notes,   either  from  the  videos  or  in  class.    Keep  notes  organized,  and
take  notes  in  more  than  one  color.
Color-­‐coding  helps  a  great  deal  in  tracking  organic  reactions.
Attend  Q+A  sessions.
There  are  many  Q&A  sessions  offered  each  week,  hosted  both  by  mentors  and
by  Dr.K.    Attend  these  sessions.    Bring  your  questions  and/or  just  bring  your  desire  to  learn.
Form   a   study   group .
Working   with   a   study   group   outside   of   class   will   help   you   learn   the   material   deeply.     Your   in-­‐class   working   group   is   a   great   place   to   form   these   connections.     Exchange   contact   information  and  follow  up  –   call  others  and  ask  if  they  want  to  study  together .
Make  and  study  flash  cards .    These  are  especially  useful  for  developing  your  mental  encyclopedia  of
reactions  and  terminology.
Use  electronic  resources.
Mastering  Chemistry  offers  a  “study  area”  with  a  host  of  practice  multiple-­‐ choice  problems.  Google  can  provide  a  wealth  of  extra  practice  problems,  too.
Venues  for  extra  help  with  261 :
1) The  Learning  Center  coordinates  free  tutoring  by  appointment:   http://learningcenter.unc.edu/services/Math%20and%20Science/tutoring-­‐for-­‐math-­‐and-­‐sciences
2) The  chemistry  department  recommends  tutors  for  hire:   http://www.chem.unc.edu/undergrads/index.html?display=help___resources&content=tutoring

2/4
2/6
2/9
2/11
1/12
1/14
1/16
1/19
1/21
Tentative  Schedule
Date   Day   Topics/Skills
1/7
1/9
W
F
Chemistry  101  review:  electronic  structure,  electronegativity,   structural  formulae,  covalent  bonds,  Lewis  Structures
Relevant  Text  Sections/Events
1.0  –  1.4
Chemistry  101  review:  Lewis  Structures,  formal  charges,  resonance   1.4;  8.3  –  8.6;  1.5  –  1.8
1/23
1/26
1/28   W
1/30   F
2/2
M
W
F
M
W
F
M
M
Chemistry  101  review:  atomic  and  molecular  orbitals,  hybridization   1.9  –  1.13
Chemistry  101  review:  hybridization  &  molecular  geometry
Bronsted  and  Lewis  Acids
MLK  HOLIDAY:  No  Class
Bronsted  and  Lewis  Acids  ;  Alkane  Nomenclature;  Functional
Groups
Acyclic  alkane  conformations:  C-­‐C  bond  rotation
Cycloalkane  conformations;  Thermodynamics  of  equilibrium
Chirality,  enantiomers
R  and  S  naming,  Optical  activity,  and  enantiomeric  excess
Multiple  stereocenters
1.14  –  1.16;  2.1  –  2.5
2.6  –  2.9,  2.12
-­‐
3.1  –  3.6;  5.5;  3.7;  7.2
3.8  –  3.10
3.11  –  3.15;  pp.  206-­‐207
4.1  –  4.6  (skip  Fischer  projections)
4.7  –  4.10
4.11  –  4.14
2/13
2/16
2/18
2/20
2/23   M
2/25   W
2/27
3/2
3/4
3/6
3/9-­‐3/13
W
F
M
W
F
M
W
F
F
M
W
F
Time  permitting:  Resolution,  enantiomers  in  nature
Exam  1     alkene  structure,  stereochemistry,  curved  arrows ozonolysis,  hydrogenation,  alkene  stability   stereoselectivity  in  addition  rxns,  synthesis
Alkyne  reactivity,  Alkynes  +  HX,  X2
Alkyne  hydration  +  tautomerization,
kinetics,  +  thermodynamics  in  the  context  of  electrophilic  addition   of  HX  to  an  alkene,  cation  stability,  Hammond  Postulate
Markovnikov’s  Rule,  Addition  of  H
2 rearrangements
O  and  ROH,  carbocation   hydroboration,  X2  addition,  peroxyacid  oxidation
Addition  of  H2  to  alkynes,  Alkyne  deprotonation,  C-­‐C  bond   formation
Review  and  multistep  synthesis
Exam  2
Dienes
SPRING  BREAK:  No  Class
(4.15  –  4.16)
5.1  –  5.6
6.1  –  6.3  (Background:  5.7;  5.9  –
5.12  (skip  p.215))
6.4  –  6.7
6.8–  6.10
6.11  –  6.13
6.14  –  6.15,  6.18
7.1,  7.4  –7.6
7.7  –  7.8
7.9  –  7.11
7.12
8.17  –  8.18

3/16   M
3/18   W
3/20   F
3/23   M
3/25   W
3/27   F
3/30   M
4/1   W
4/3
4/6
F
M
4/8   W
4/10   F
4/13   M
4/15   W
4/17   F
4/20   M
4/22   W
4/24   F
5/05   Tu
5/05   Tu
Tentative  Schedule,  Continued
SN2
SN1
SN1/2  competition
Intramolecular  substitution  reactions  and  biological  examples
E2
E1
Stereochemistry  of  elimination
SN1/2  vs.  E1/2  and  synthesis
HOLIDAY  BREAK:  No  Class
Intro  to  alcohols
More  on  alcohols
Oxidation  of  alcohols,  ethers
Exam  3
Epoxides,  thiols
Intro  to  radical  halogenation
Reactivity  and  selectivity  in  halogenation;  radical  additions  to   alkenes
Allylic  and  benzyllic  halogenation;  synthesis  with  radicals
REVIEW
8:00  am:   Final  Exam  for  section  002
12:00  pm:  Final  Exam  for  section  001
9.1  –  9.2
9.3  –  9.4
9.5  –  9.6
9.8  –  9.9
10.1  –  10.2
10.3  –  10.5
10.6  –  10.7
10.9    –  10.10
11.1  –  11.2
11.3  –  11.4
11.5  –  11.6
11.7;  11.11  –  11.12
13.1  –  13.3
13.4  –  13.5,  13,7
13.8  –  13.10