Skyline College A.J. Bates Professor of Chemistry

     Chemistry 235-238 - Organic Chemistry 2 - Fall 2014

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

Wednesday, December 24

  • Thank you for a fun and rewarding semester! Enjoy the Winter Break!


Sunday, December 14

  • CHEM 235:

    • Correction: Question 1A on the previous semester product should be the meta, not para product.


Thursday, December 9

  • CHEM 235:

    • Skyline College Classes are CANCELLED for Friday, December 12. I will answer questions by email tomorrow, but will not have much opportunity to respond to emails over the weekend. Feel free to send photos of problems or your work to make communication of your questions easier.

    • Please note that the FINAL EXAM is scheduled from 8:10 - 10:40 AM on
      Monday, December 15.
      It was incorrectly given as pm on the syllabus, but is correct on the online course calendar.

    • The EYH Mailing has been rescheduled. Your help is still needed! A few bonus points will be awarded for participation:
      • Tuesday, December 16
      • Place: 7-338 (CHEM Lab)
      • Time: 11am - 1pm



Tuesday, December 9


Monday, December 8


Wednesday, December 3


Sunday, November 23

  • CHEM 238: On Tuesday, we will complete the Aldol Experiment for those of you who still have work to do on that experiment. We will not begin another experiment this Tuesday. That will be our only activity for Tuesday's lab session.


Thursday, November 20

  • CHEM 235: The PS #8 Answer Key and an Extra Practice Worksheet with Answer Key are posted on the LECTURE page.


Tuesday, November 18

  • CHEM 235 Exam #4 Announcements & Review:

    • You may start the exam as early as 9:45 am, on Monday, November 24.
      The exam will end at 11 am.

    • Chapter 19
      • Acidity/basicity as it relates to organic combounds - carboxylic acids, phenols, amines, and solubility & separations.
      • Acidity/basicity and relationship to inductive effects and resonance effects.

    • Chapter 20
      • Metal Hydride Reactions: LAH, NaBH4, DiBAL-H,LiAlH(O-tBu)3
        • Reactivity & Mechanisms (including amide to amine reduction)
      • Grignard / Alkyl Lithium Reactions
        • Reactivity & Mechanisms
      • Protecting Groups
        • t-Bu ether as a protecting group (covered only in lecture)
        • Silyl ether as protecting group (please see the text)
      • OrganoCopper Reagents
      • Reactions of alpha-beta unsaturated carbonyls
        • Catalytic Hydrogenation & Organometalics
      • Retrosynthetic Analysis
        • Review Oxidations
        • Review PBr3 Reaction (alcohol to alkyl bromide)

    • Chapter 22
      • Esterification-Hydrolysis / Transesterification
        • Acid-catalyzed Mechanism & Reversability
      • Saponification (Base-promoted Hydrolysis)
      • Conversion of a carboxylic acid to acid chloride (SOCl2)
      • Reactions of Acid Chlorides & Anhydrides


Thursday, November 13

  • CHEM 235: PS#8 is posted. It will be due in lecture next Wednesday.


Wednesday, November 5


Thursday, October 30

  • CHEM 235:

    • As announced in lecture (and like our previous exams), you may start the exam as early as 9:45 am tomorrow, with it ending at 11 am.

    • Problem Set #7 Answer Key corrections:
      • Q1: One extra C is in the structure of the final product.
      • Q9: The final workup step should have HCl as the acid (instead of NaHCO3).
  • CHEM 238:

    • A few notes on the Formal Lab Report for p-nitroaniline:
      • Pay close attention to the mole table and stoichiometric analysis (as discussed).
      • The mechanism is one of the primary means by which you demonstrate your understanding of the theory behind the reaction. In the discussion, be sure that you pay close attention to all aspects of the mechanism:
        • Electrophile formation
        • EAS, including all resonance structures of the intermediate
        • Removal of the acetyl group from nitrogen
      • I will accept the lab report for full credit up to 4:30 pm on Wednesday, November 5.

      p-nitroaniline IR spectra (literature and student spectrum)
      • Please print and interpret these spectra as part of your report, instead of the one originally provided. It was a spectrum from a Nujol mull - a procedure we did not use.
      • Note: if you acquired your own specturm, interpret it in lieu of the student spectrum provided.

    • Grade posting
      • Grades are posted by your 5-digit code number. For lecture students, it is the same code number as for CHEM 235. For lab-only students, pease check your email account for the code in a message from me.

    • The lab exams are graded and may be picked up from me shortly before the CHEM 235 exam (which starts Friday at 9:45) or during my office hours (see the course calendar for times).


Thursday, October 23

  • CHEM 235:
    • Reminder: PS #6 is due tomorrow at the start of lecture.
    • Problem Set #5 Answer Key is posted.
    • Chapter 17 & 18 end-of-chapter problems are now assigned.
    • Problem Set #7 is also posted. It will not be collected, but you will receive 5 points for it.
  • CHEM 238:
    • Please see the course calendar for our lab activities next Tuesday.
    • Please print and bring the following to lab on Tuesday:
      • C-13 NMR Notes Handout
      • C-13 Peak Correlations Chart
      • NMR PS #3
      • The handout for Experiment #6: Grignard Reaction (from WEBACCESS)
        • We will discuss the experiment and clean & dry the glassware.


Monday, October 20


Monday, October 13


Wednesday, October 8

  • I am not feeling well today and will not be making it to campus. I am canceling classes for today, Wednesday, October 8, 2014.
  • The following reflects our current and upcoming lecture topics. End-of-chapter problems will also be posted in the next few days.
    • Chapter 17 - Aromatic Compounds
      • End-of-Section Problems: 3-5,8,10-13,16-19,21,22
    • Chapter 18 - Reactions of Aromatic Compounds
      • End-of-Section Problems: 1,3-12,14-25,30-33


Monday, October 6

  • CHEM 238:
    • Lab Test #1 will be administered in LAB on Tuesday, October 21.
    • The NMR PS#2 may be submitted up to 10:10 am on Friday, October 10.
    • Other due dates and lab plans remain unchanged.
    • The changes are reflected on the course calendar.


Thursday, October 2

  • CHEM 235 Reminder: As announced in class, you may start Exam 2 as early as 9:45 am on Friday, October 3. The exam will end at 11 am.


Thursday, September 25

  • CHEM 238:

    • Please submit the Diels-Alder report as a hardcopy or a highly readable, single electronic document by NOON tomorrow, Friday, September 26.

    • NMR PS #2 is posted. It will be due on October 7 at 1:10pm.
      • I recommend starting this assignment soon. The questions on this problem set are more challenging than on the first NMR problem set.

    • Next Tuesday, we will discuss the Relative Reactivities Experiment (Expt. #3). The mini-report will be due the following Tuesday (October 7) at 1:10pm.

    • Next Tuesday (Sept. 30), we will also carry out Experiment #4 (Friedel-Crafts Alkylation).


Friday, September 19

  • PS #4 is posted on the lecture page - it will be due next Friday at 10:10 am.
  • The Exam #1 answer key is posted on the lecture page.
  • Please note that my office hours have changed sightly for next week, including moving the Friday time to before lecture. See the calendar for specifics.
  • Please consider attending a lecture to be given this coming Monday! I am offering a bonus opportunity for this lecture. If you attend and write a half to full-page summary of the talk, you will earn 3 bonus points - a small incentive to attend, but it should be a very informative talk.
    • Dr. Ryan McOmber Cooper
    • Monday, September 22nd • 4:30–5:30pm • Room 7106
    • Background: Dr. Cooper went to India on an MIT fellowship program to work with a startup, under the Indian Institute of Informational Technology, to develop mobile devices, connected through smart phones to facilitate healthcare in the villages, which have little access to doctors. Key goals included ease of use, using technology available in India and at a price that would work with the Indian economy. Ryan will talk about this effort.
  • Gay-Straight Alliance: First meeting is on Tuesday, September 23. All members of the Skyline College community are welcome to attend. Please pass on the word to friends and groups at the college!

    GSA Flyer


Thursday, September 18

  • CHEM 235:

    • I will make the exams available to you as early as 9:45 am to allow you a short time to review before lecture. I will briefly discuss the exam statistics at the start of lecture, but we will use the lecture time to cover new material and to work on some sample problems from the textbook. I will be available in office hours following lecture to answer questions on the exam.

    • Please bring your textbook to class on Friday. If you have the loose-leaf version, please bring chapters 15&16. Bringing the answer book is not required, but you may find it helpful.

    • Book problems from Chapters 15 & 16 are posted.
      • In Chapter 15, we will be focusing on the sections on the reactions and mechanisms associated with radical halogenation, radical hydrohalogenation, and polyethylene derivative polymerizations. We will also consider the allyl radical structure and allylic bromination with NBS (mechanism not required). There will not be a significant focus on the ?H's associated with the various mechanistic steps for our course.
      • In Chapter 16, we will be covering the chapter in its entirety. Sections 16.1-16.5 are primarily review.


Tuesday, September 16

  • CHEM 238: I am not feeling well today and I have decided to cancel lab. I will be pushing back activities and due dates in the lab by 1 week.


Monday, September 8

  • CHEM 235: Problem Set #3 Correction - Please note that on three of the problems the compound potassium dichromate had the wrong formula. The formula should be K2Cr2O7. It was a typo, copied & pasted twice. It is a source of CrO3 oxidizing agent. The corrected problem set is posted. You are not required to reprint it.
  • CHEM 238: NMR Problem Set #1 Clarification - The second spectrum is for a compound with the formula C5H10O


Friday, September 5

  • CHEM 235 Review Session:
    • Monday, September 8, 8:45-9:30am in 7-304 (lecture room)
    • Will cover review topics from Organic Chemistry 1 - those particularly important to our Exam #1 and to the course generally.
    • Will be followed by regular office hours from 9:30-10 am (open to all classes), and then lecture at 10:10 am.


  • CHEM 235 Quiz #1 Information:
    • Quiz #1 Answer Key
    • Quiz #1 Average: 10/25 (40%)
    • Quiz #1 Standard Deviation: 5/25 (20%)
    • Quiz #1 Score Adjustment:
      • If the percentage you score on Exam #1 is higher than your Quiz #1 percentage, then your Quiz #1 percentage will be replaced by your Exam #1 percentage.
      • This applies only to Quiz #1 and is not likely to be repeated on any future quiz or exam.
      • If you did not do as well on Quiz #1 as you had hoped, make adjustments to the way that you are preparing for the course, so that you will be prepared for Exam #1. The score adjustment offered on Quiz #1 means that a low grade on it will not hurt your overall grade if you make necessary improvements for Exam #1.
      • If you did well, make sure that you are contnuing to properly prepare for the Exam, including newer material. As the semester progresses, you may find that it will take more preparation outside of class to continue to master the concepts.
  • CHEM 235: An extra practice worksheet is posted on the LECTURE page. An answer key and additional extra practice will be posted in the coming days.
  • CHEM 235: Exams from Fall 2007 and Exam #1 from Fall 2008 are posted on the website. Please note that these reflect a different ordering of material in the course. They are provided primarily to give you a sense of the style of the exams that will be given in the course.


Wednesday, September 3

  • CHEM 235: Problem Set #3 • Due Tuesday, September 9 by 1:10 pm
    • Hardcopy or electronic submission is OK.
    • You may slide hardcopies under the door of my office or hand them into me in lecture or the start of lab on Tuesday.
    • For electronic submissions, be sure that the files are easily readable. I recommend scanning in B&W or grayscale. For smartphone or tablet photos, be sure to brightly light your paper and photograph such that the line of sight is as close to perpendicular to the page as possible.


Friday, August 29

  • CHEM 235: Reminder - Quiz #1 will be given in lecture on Wednesday, September 3. Topics will include:
    • Organic Chemistry 1 Review:
      • Substitution, Elimination, and Addition Reactions and Mechanisms
      • Basic Chemical Structure, including orbital diagrams, resonance, and stereochemistry
    • Lecture topics, readings, and problems relating to Chapter 12, Sections 12.1-12.9A.
  • Chapter 12 End-of-Chapter Problems are posted.


Thursday, August 28

  • CHEM 238 Students: Please see the laboratory page for the Eliminations Experiment Class GC Data and the notes handouts and reference materials for the upcoming lab lecture on NMR (next Tuesday). Reminder: Your prelab for the Diels-Alder experiment and the lab report for the Eliminations Reactions and GC Analysis experiment will be due next Tuesday.
  • Students ONLY enrolled in CHEM 235: NMR is an indepedent study topic for the lecture course. It is strongly recommended that you attend the lab sessions where NMR will be lectured. If that is not possible, the textbook reading in Chapter 14 gives a good introduction to the topic. You should also review the lecture notes and example problems on the web page. The first NMR lecture in the lab will be next Tuesday at 1:10 pm ~2:30 pm.


August 22, 2014


August 21, 2014

  • The GC Technique handout and prelab questions are now posted on WebAccess.
    • Note: The PRELAB questions to answer (#1,2,4) are in a separate file from the technique.


August 19, 2014

  • CHEM 238 Laboratory will start at 1:30 pm today. We will clarify the start time for future lab sessions today.


August 2014

  • Welcome to Organic Chemistry 2 for Science Majors - CHEM 235 / 238
  • CHEM 235: Our first lecture will be on Monday, August 18 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 19 at 1:10pm in 7-341. We will cover safety, have our first lab lecture, and check into lab drawers on this day.
  • Review & Getting started:
    • I recommend that you review the textbook chapters relating to CHEM 234 topics (1-11), paying close attention to the reactions studied. You can find Extra Practice Worksheets titled REACTIONS on the LECTURE page from CHEM 234 for Spring 2013.
    • You may also want to review earlier material related to bonding, nomenclature, stereochemistry, and related topics if it has been some time since you completed the first semester course. Additional worksheets relating to those areas are also available on the CHEM 234 lecture page.
  • 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.