Skyline College A.J. Bates Professor of Chemistry

     Chemistry 235-238 - Organic Chemistry 2 - Fall 2015

Chem 210 - General Chemistry 1Chem 235-238 - Organic Chemistry 2
Chem 220 - Lab Manual & Extra Practice ProblemsScience Lecture Series
Gay Straight Alliance

Announcements & Important Course Information

Tuesday, November 24

  • CHEM 235 & CHEM 238: Additional updates may be made to the website through Wednesday evening.
  • CHEM 238:
    • Please see the course calendar for updated due dates (as discussed in lab)
    • For Experiment #9 (Aldol Condensation), Please prepare an abbreviated report:
      • Mole Table Analysis (including percent yield)
      • Melting Point Analysis
      • IR Spectrum and Analysis
      • Post-Lab Questions: 2,4,5 only


Thursday, November 19

  • CHEM 235:


Monday, November 16


Sunday, November 15

  • CHEM 235: A new Sapling Problem Set is posted. It will be due Monday, November 23 at 9pm.


Saturday, November 14


Friday, November 13

  • CHEM 238:

    • Please check back over the weekend for updates, including the current grade posting.

  • CHEM 235:

    • Slides for Chapter 21 - Part B
    • The Chapter 21 Problem Assignment is now posted on the lecture page.

    • Exam #3 Answer Key

    • Current Grade Posting
      • This posting reflects the grade you have earned so far, and provides an ESTIMATE of what your grade would be with a low exam score grade adjustment that will be applied to calculate your final grade in the course:
        • Your lowest lecture exam score will be replaced by the average of your lowest lecture exam score and your two highest lecture exam scores, OR by the average of your lowest lecture exam score and your final exam score, whichever is better.

    • Please check back this evening or tomorrow for the next Sapling problem set assignment.

    • Additional powerpoint notes slide will be posted by Monday morning.


Thursday, November 5

  • Class is cancelled for tomorrow, Friday, November 6.
  • I will make some updates to the website over the weekend.
  • Also remember that Monday is a holiday and there will be no classes.


Wednesday, November 4

  • CHEM 235: Please check back tomorrow for updates to the website.
  • CHEM 238: Please check back tomorrow for additional updates to the website.

    • Experiment #7 (Synthesis of p-nitroaniline) will be completed in lab next Tuesday (11/10). Please prepare a standard report for the experiment. It will be due Friday, November 20.

    • We will not be starting a new lab next week, so no prelab will be due.

    • Experiment #6 (Friedel-Crafts) Report is DUE in lab next Tuesday (11/10).
      • This is a postponement of the original Friday DUE date.
      • Notes related to the report requirements are posted on the course lab page.

    • Experiment #8 (Wittig Reaction)
      • The experiment handout is now posted. Please note that this is a different order than was originally planned. We will perform this experiment on 11/17, when its prelab will be due.

    • Lab Test #2 is postponed to Tuesday, December 8.

    • I have updated the lab schedule through the end of the semester.


Sunday, November 1

  • CHEM 235: Slides for Chapter 21 - Part A


Friday, October 30

  • CHEM 235:
    • As announced in lecture today, there will be an Exam #3 Review Session on Monday (11/2) at 9:25 am in the regular lecture room.
    • A new note set will be posted for Chapter 21 by Sunday evening.


Tuesday, October 27

  • CHEM 235:
    • On Reactions 8, the last question should read:
      • Provide an explanation (including structures) to explain why bromobenzene is less reactive than benzene to EAS, but is still an ortho/para director.
    • The answer key to Reactions 8 is now complete.
  • CHEM 238:
    • Experiment #6 (Friedel-Crafts Reaction)
      • Please prepare a standard laboratory report.
        • Note that the Discussion Questions in the lab handout direct you to do much the typical data analysis. Be sure include the mole table, complete IR analysis (including the out-of-plane bending mode analysis- see the table in the handout), melting point analysis, and a discussion of the experiment, including the reaction and a complete arrow-pushing mechanism for one of the alkylation steps.
        • In the mechanism, be sure to include the formation of the electrophile and all important resonance structures for the intermediate and the arrows to move from one to the next.
        • Please answer the Questions at the end of the handout as Post-Lab Questions.

    • Experiment #7 (Synthesis of p-nitroaniline) is now posted on WebAccess. Please prepare a standard prelab for this experiment, including the MOLE TABLE that you will use in the experiment. The prelab is due next Tuesday at the start of lab.


Monday, October 26

  • CHEM 238:
    • The Experiment #5 Report (Relative Reactivities) will be due on Friday, October 30 by 1pm.
    • The Prelab for Experiment #6 (Friedel-Crafts) is due tomorrow in Lab (Oct. 27).
  • CHEM 235:

    • Exam #3 has been postponed to Wednesday, November 4 in lecture.

    • Problem Set #8 will now be due by 6pm on Saturday, October 31.

    • Please see the LECTURE page for worksheet answer key updates.

    • There is an IMPORTANT CORRECTION to the Reactions 6 #1F. The structures for the answer were inadvertaently drawn with the double bond in the wrong position. It is now corrected:
    • Please note that the reagent on the second reaction on last slide of the Ch. 18 Note Set Part B should be corrected to a reagent of butyryl chloride. (Previously the Cl had been left off). This correction was made in lecture today.


Saturday, October 24


Friday, October 23


Tuesday, October 20

  • CHEM 238 Announcments & Information:

    • Lab Test #1 Answer Key

    • Experiment #5 (Relative Reactivities):
      • Class Data
      • Important Note: Acetophenone is usually deactivating relative to toluene; however the class consistently observed that it was activating in our experiment. For question 7 & 8 of the revised Discussion & Conclusions questions, treat it as a deactivating meta- directing group, as would be expected.
      • The Lab Report should consist of your data, the class data with your generalizations, and answers to the Revised Discussion & Conclusions and Post-Lab Questions (handout provided in lab). It is due next Wednesday (10/28) by 3pm. If it is turned in by the start of lab on Tuesday (10/27), I will be able to provide feedback to you prior to next Friday's lecture exam.

    • Experiment #6 (Friedel-Crafts Reaction) is now posted on WebAccess. Please prepare a standard prelab for this experiment, including the MOLE TABLE that you will use in the experiment. The prelab is due next Tuesday at the start of lab.


Sunday, October 18

  • Please see the calendar for my office hours this week. Due to various meetings and other obligations, I have had to move some times around, including my Tuesday morning office hours.
  • CHEM 235 - New notes links:
    • Chapter 18 - Aromatic Reactions


Wednesday, October 14

  • CHEM 238 LAB:
    • Reminder: A standard prelab - Heading, Purpose, Reaction (general - just one for the whole experiment), Procedure, and Data Table; no prelab questions - will be due for next week's experiment on the Relative Reactivities of Some Aromatic Compounds.


Wednesday, October 7


Tuesday, September 29

  • CHEM 238 LAB: Lab is cancelled today due to instructor illness.
  • CHEM 235 LECTURE: I do plan to be back to campus tomorrow and we will hold the review session at 9:15-10am in the lecture room before lecture at 10:10am.
  • CHEM 235 LECTURE: Please see the LECTURE page for the answers to the Extra Practice Worksheets posted yesterday. I have also posted notes relating to two of the questions on the Reactions 4 worksheet.
  • CHEM 238 LAB: NMR Problem Set #2
    • Note: In the case of alcohols on these problems, the alcohol proton is NOT coupled to the H’s on adjacent C’s due to H-bonding. Therefore the O-H proton does not participate in the splitting pattern, and itself appears as a broad singlet.

    • Example: Ethanol (CH3CH2OH):
      • The O-H proton is NOT coupled to the -CH2- protons in the structure
      • The signal for the proton on the oxygen is a broad singlet.
      • The methyl and methylene group give the typical splitting pattern of an ethyl group, showing no influence of the OH proton.


Monday, September 28

  • Please see the LECTURE page for additional worksheet postings.
  • Exam #2 Review Session: Wednesday, Sept. 30 at 9:15 in the lecture room (7-304)
  • Exam #2 Topics:
    • Cr(VI) oxidation reactions
    • NaBH4 Reductions
    • LiAlH4 Reductions (including alkyl halides and epoxides - discussed prior to Exam #1)
    • DIBAL-H and Li(t-BuO)3AlH Reductions
    • Grignard and Alkyl Lithium Reactions
    • Protecting Groups
    • Organocuprate reactions including a 1,4 addition
    • Radical Stability (including allyl radical and resonance)
    • Radical Halogenation of an Alkane
    • Radical Hydrohalogenation of an Alkene
      • Contrast to Acidic Hydrohalogenation of an Alkene


Saturday, September 26

  • Please see the LECTURE page for Ch. 17 & 18 Notes posting.
  • The answer key to the Grignard worksheet is now posted.
  • PS #5 is posted on Sapling Learning.


Wednesday, September 23

  • Please see the LECTURE page for a new practice worksheet on Grignard reactions.


Friday, September 18


Wednesday, September 9


Monday, September 7

  • CHEM 235 Students:

    • Exam #1 Reactions Sheet
      • For Exam #1 this Friday, you will be provided with the above handout, a pKa chart, and a Periodic Table

    • As announced, you are welcome to attend lectures on NMR and other spectroscopic interpretations that will be presented in the lab (room 7-341). The first will be tomorrow in lab at 1:10 pm. It will be an overview of NMR. The second lecture will be the following Tuesday at the same time and will focus on spectral interpretation. See the lab page for the notes handouts.
  • CHEM 238 Students:
    • Reminder: As discussed next week, lab will be meeting from 10am-3pm.
      The breakdown of time for activities in lab is as follows:
      • Experiment #2 (Diels-Alder) Completion: 10am-1pm - IR and MP analyses
      • Lab Lecture: 1:10-3pm
        • Introduction to NMR Spectroscopy (See the lab page for the notes handouts)
        • Experiment #3 - NaBH4 Reduction


Sunday, August 30

  • CHEM 235 Students:
    • A new problem set is posted on Sapling Learning.
    • On the lecture page, I have posted links to many review and newer reaction animations / computer models that should be helpful as you try to visualize reaction mechanisms.
  • CHEM 238 Students:
    • Student GC data for the Elimination Reactions experiment is posted on the course website.
    • The lab report will be due no later than 4pm on Wednesday, September 2. This will give you an opportunity to ask any final questions you might have on the class data interpretation on Tuesday in lab.
    • WebAccess: The Diels-Alder Theory worksheet is now properly linked. Two links to computer models of pertinent Diels-Alder reactions were added.
    • The prelab for the Diels-Alder experiment is due at the start of lab on Tuesday.


Friday, August 28


Tuesday, August 25

  • CHEM 235 Students:

    • As announced yesterday in lecture, we will not be meeting in class on Wednesday, August 26.

    • Please use this time to review the powerpoint slides for Chapter 11 on Alkynes and the start of the Chapter 12 notes on the hydrogenations of alkenes and alkynes (slides 1-14).


Friday, August 21

  • Sapling Learning Problem Set #2 will be posted today.
  • The review worksheet key is available on the lecture page.
  • A number of tutorial and animation reviews are posted on the lecture page.


Pre-semester Announcements

  • Welcome to Organic Chemistry 2 for Science Majors - CHEM 235 / 238
  • CHEM 235: Our first lecture will be on Monday, August 17 at 10:10am in 7-304. We will briefly cover course requirements on the syllabus and begin our first lecture/discussion.
  • CHEM 238: Our first laboratory meeting will be on Tuesday, August 18 at 1:10 pm in 7-341. We will cover safety, have our first lab lecture, and check into lab drawers on this day.
  • Required Lecture Textbook (CHEM 235): The required course text, Organic Chemistry, 4th ed. by Janice Gorzynski Smith, is available as a custom edition in the Skyline College Bookstore. It is bundled with the Study Guide and Solutions Manual. I highly recommend buying this set. The solutions manual includes complete solutions to all of the questions in the text. The reading and questions assigned from the text will be one of your key means of study and preparation for the course and exams.
  • Laboratory Manual (CHEM 238): The CHEM 238 Laboratory Manual will be available online through the WebAccess site for the course. A direct link is available on the LABORATORY page.
  • Review & Getting Started:
    • The lecture course will start with an intensive review of Organic Chemistry 1:

      • We will review substitution, elimination, addition, and acid-base reactions with a focus on mechanisms, predicting products, stereochemistry, regioselectivity, and retrosythetic analyses.

      • Please see the LECTURE page (link to the left) for reading assignments and book problems from Chapter 9,10, and 11. These chapters will be the focus of our review. You may want to get a jump start for the class by reviewing these chapters and working the assigned problems from the reading sections.

    • I recommend that you review the other textbook chapters relating to CHEM 234 topics (1-8) to review bonding and molecular structure, nomenclature, stereochemistry, and acid-base chemistry.

    • For additional review and practice, you can find Extra Practice Worksheets on the LECTURE page from CHEM 234 for Spring 2015.

  • Sapling Learning Online Homework System (CHEM 235)

    • Please Register for the Sapling Learning Online Homework System for CHEM 235.
      Graded problem sets will be assigned on this service.

    • A Training Problem Set is posted under the Introduction section. It is not required, but I think you will find it helpful, especially for using the chemical structure drawing functions.
      • Questions 1-12 - General use of Sapling Learning
      • Questions 13-22 - Use of the chemical structure drawing functions
    • The first Graded Problem Set is posted under the Problem Sets section. See the course calendar and/or Sapling site for the due date/time.
      • For this problem set, you have UNLIMITED attempts to answer each question with NO POINT DEDUCTION.

  • Please visit the links to the left for other information related to the courses. The website will be the primary way that I will provide materials and communicate information to you outside of class time. Check back regularly - there will be frequent updates.


Academic Integrity

  • Academic integrity is an important issue in all academic settings, and will be taken very seriously by the instructor of this course, and the college generally. This topic will be addressed in detail in the first week of classes in lecture and in lab.

  • I recognize that most students conduct themselves with honesty and integrity. I also recognize that the actions of a few dishonest students and the impact of those actions on the academic process necessitate a frank and ongoing discussion of this issue.

  • Please review the Student Handbook information on Academic Integrity.