Chem 201 Homework Solutions

Elements of Organic Chemistry, CHM 201
Dr. Laurie Starkey, Cal Poly Pomona

Dr. Starkey's Organic Chemistry Day 1 - What to Expect (& student testimonials) | How to Earn an A | OLC rosters | Blackboard journals (instructions)

Syllabus (Current or most recent, see Kahoot syllabus quiz for Day 2) and Dr. Starkey's current schedule

Online Homework - | Instructions | tech support email:

Got CHM 250L Lab? Visit Dr. Starkey's lab homepage for useful resources (technique tutorials, reagent table calculations, etc.)

Online lectures at

  • see Dr. Starkey for instructions on how to sign up
  • free access is limited to only those students who are registered in Dr. Starkey's course this quarter

Virtual Office hours:

  • Monday, 4/17, 9:30-10:30 pm: Exam I session recording (it is 1 hour, 6 minutes long so you can use navigation bar at bottom to jump ahead)
  • Wednesday, 5/10, 9:30-10:30 pm: Exam II session recording (1:12)
  • Wednesday, 6/7, 9:30-10:30 pm: Final Exam session recording (55 minutes)

Clicker Questions:

Metacognitive Resources:

Handouts/Answer Keys (for current quarter)

  • Chapter 1 handout (Bonding & Molecular Shapes)
  • Line drawing examples website
  • OLC week 1 - get to know each other! Introduce yourselves, exchange contact information, and compare schedules to find good meeting times. Share with the group: do you have a favorite memory/experience from a science class?
  • 3-D sketch homework (due Thursday, 4/6) , answer key and video of solution: sketch 1 | sketch 2 | sketch 3 | sketch 4 (includes an advanced bonus structure!). Notes about how homework credit works.
  • OLC week 2 suggested assignment: Work on the following textbook problems 1.11 add curved arrows and rank/explain (rank the given resonance forms by considering: which forms contribute more to the hybrid? which contribute less? explain), 1.47 T/F compare answers and discuss, 1.50b, 1.50d, 1.50f - draw resonance forms and rank/explain, 1.70b - draw resonance forms and rank/explain
  • Chapter 2 handout (Acid-Base)
  • Acid Strength homework (due Tuesday, 4/11) and answer key
  • Chapter 3 handout (Alkanes & Cycloalkanes)
  • Nomenclature practice websites for alkanes & cycloalkanes: Boise State | Chemware | Doc Brown | Michigan State U (1st two sections only) | Univ. of Guelph (Quiz 1 only)
  • Conformation videos: cyclohexanepart 1 (3D structure), part 2 (drawing a chair), part 3 (doing a chair "flip") || ethanemodels & energies || butanemodels
  • OLC week 3 suggested assignment: "Putting it Together" Chapters 1-3 - great Exam I review and worth +1 extra credit point on Exam I (do problems 1-19, but skip 11e, 14e, 15 and 16, and then trade papers with your group members and grade with red ink using this answer key. Turn in graded review on day of exam for extra credit.). If you are not in an OLC, you can self-grade this assignment and still earn extra credit!
  • Exam I: Blank Exam and Answer Key (histogram and Extra Credit Reflection/Survey)
  • If you are wondering "I studied SO much for this exam...why did I bomb it?!" then click here for some advice on studying!
  • OLC week 4 suggested assignment: Watch the Derek Sivers TED talk together and discuss.  Think about a “fantastic struggle” you’ve had in your own life that resulted in a successful accomplishment (e.g., learning an instrument, playing a sport, learning a new routine/skill, succeeding in a difficult course, etc.).  Share your story with your group.  Why was this goal important to you?  Were you ever close to giving up?  What motivated you to persist?  Where did you go for guidance when you needed help?  Why do you think you ultimately succeeded?

  • Chapter 4/5 handout
  • Reaction Mechanism (arrow-pushing) homework (due Thursday, 4/27) and answer key
  • Chapter 6 handout
  • Stereochemistry practice (R/S, E/Z): Virtual Textbook (Reusch)
  • OLC week 5/6 suggested assignment: B&P textbook problems 4.18 (compare/discuss IUPAC names | key) and 5.57 (provide mechanism, explain, discuss)
  • Real-world implications of stereochemistry (one enantiomer of racemic mixture caused the devastating problems) and the importance of government regulations: the story of Thalidomide (video 12.5 minutes long)

  • Chapter 7 handout
  • OLC week 6/7 suggested assignment: try to prepare your own chapter summaries (outline of Ch. 4/5/6/7) by writing down everything you know about each topic. Compare with group members, go through lecture notes and add details.
  • Clicker credit: +1 point will be given on Exam II for anyone who is using a clicker in CHM 201 this quarter. Please click on this survey link to "register" your clicker for this class (you will need to enter your Bronco name/password to access the form). Have your clicker handy when you do the survey because I will ask for your clicker number. If you can't read your barcode number, enter "none" for the code and please show me your clicker next week.

    Reaction Mechanism Animations
  • Chapter 7 Predict the Product answer key
  • Exam II, Blank Exam and Answer Key (histogram)

  • Chapter 8 handout
  • Dehydration Mechanism homework (due Thursday, 5/19) and answer key
  • Cool demo:potassium + water = BOOM! (e.g., an explosive way to make hydroxide from water, or an alkoxide from an alcohol)
  • Chapter 12 handout
  • OLC week 8/9 suggested assignment: work on Grignard/Hydride homework
  • Grignard and Hydride homework (due Thursday, 5/26) and answer key
  • Chapters 13/14 handout
  • Carboxylic Acids, Esters, Ketones & Aldehydes Nomenclature practice problems and answer key
  • Carboxylic Acid Derivatives Predict the Product practice problems and answer key (see narrated version on YouTube!)
  • OLC week 10 suggested assignment: work on "Final Review Practice" thirty bonus clicker questions listed above. Try each on your own and then compare answers and discuss. Answer Key is also provided above.

  • Suggested Textbook Problems (Brown & Poon 5th or 6th edition)

    Chapter 1 Bonding and Molecular Shapes (lecture handout): 1–12, Quick Quiz (skip Functional Group questions), 17–51 (odd only), 63, 65, 67.

    Chapter 2 Acids and Bases (lecture handout): 1–6, Quick Quiz, 7–33 (odd only, skip 23) (NOTE: you should be able to do the following Ch. 2 problems WITHOUT using a pKa table: 3b, 4, 15, 19d, 25d, 33a, 33c)

    Chapter 3 Alkanes and Cycloalkanes (lecture handout): 1-5, 7-12, Quick Quiz, 13–53 (odd only, skip 23, 29, 45). "Putting it Together" Chapters 1-3 - great Exam I review and worth +1 extra credit point on Exam I (do problems 1-19, but skip 11e, 14e, 15 and 16, and then trade papers with your group members and grade with red ink using this answer key. Turn in graded review on day of exam for extra credit.).

    ========================== Exam I, Tuesday April 18 ================================

    Chapter 4 Alkene and Alkyne Nomenclature & Structure, Study of Chemical Reaction (Ch 4/5 lecture handout): ALL in-chapter problems 1-6, Quick Quiz and odd end-of-chapter problems 7-45 (SKIP section 4.4 and SKIP problems 35 and 43, and 6th edition SKIP problem 4.4d)

    Chapter 5 Reactions of Alkenes and Alkynes: in-chapter problems 1-6 and 8, Quick Quiz (SKIP 2, 3, 7, 8, 13, 16, 17, 26) and odd end-of-chapter problems 11-49 (SKIP sections 5.3C, 5.5 and 5.7 and SKIP problems 21, 23, 31, 33, 39, 41, 43, 45d, 47a, 49d and 6th edition SKIP problem 5.45f)

    Chapter 6 Stereochemistry (lecture handout): ALL in-chapter problems 1-6, Quick Quiz and odd end-of-chapter problems 7-45 (SKIP problems 23b, 25bd, 41 and 6th edition SKIP problem 6.2b). "Putting it Together" Chapters 4-6 (good practice, not extra credit this time...check your work with this answer key: page 1 and page 2): do problems 1, 2, 4, 5, 7, 12, 13, 18, 21bcdef, 22 (like hydration of an alkene - start by protonating the pi bond, rearranging the carbocation, and then do an intramolecular attack of a nucleophile...).

    Chapter 7 Substitution Reactions of Alkyl Halides (RX) (sections 7.1 - 7.6 only, lecture handout):
    in-chapter problems 1-5, Quick Quiz (SKIP 4, 5, 7, 16, 19, 20) and odd end-of-chapter problems 9-35, 41ac, 43abef

    ========================== Exam II, Thursday May 11================================

    Chapter 8 Alcohols (ROH) (8.1, 8.2 and 8.3A-C only lecture handout): in-chapter problems 1-8, Quick Quiz (SKIP 2, 3, 10, 11) and odd end-of-chapter problems 13-45 (SKIP sections 8.3-8.6 and SKIP problems 27, 33, 41c, 43h, 45def)

    Chapter 12 Aldehydes & Ketones (lecture handout):
    in-chapter problems 1-6, 10, 12, Quick Quiz (skip 15, 20), and end of chapter problems 13-27 (odd), 35, 39a-g, 43ac, 45bcd, 53 (SKIP problem 13d, 17e and sections 12.7 and 12.9).

    Chapter 13 Carboxylic Acids (Ch 13/14 lecture handout):
    in-chapter problems 1-6, Quick Quiz (skip 2, 15), and end of chapter problems 9-39 (odd, skip 9ad) and 47abcefil (SKIP sections 13.7 and 13.8).

    Chapter 14 Carboxylic Acid Derivatives:
    in-chapter problems 1-8, Quick Quiz, and end of chapter problems 9-35 (odd) and 39ab.

    =====================Final Exam, Thursday, 6/8 (11:30 am - 1:30 pm)=======================

    • Cumulative final exam, Chapters 1-8, 12-14
    • Final exam is all multiple-choice (bring Scantron)

    Sample Exams (Why are there no answer keys? What is the best way to study for an exam? Click here to find out!)

    Last updated June 7, 2017.

    The following does not apply to Fall 2017. Please visit the Moodle pages for all Chem 201 course info.


    There will be two kinds of in-class exams: five short quizzes (20-35 minutes) and one multi-hour final exam. In addition, each in-class quiz will be accompanied by a take-home quiz (due 24 hours after the in-class quiz). This page contains ground rules for all exams, in-class and take-home. It also contains a tentative exam schedule and sample exams from 2015 (with answers).

    QUIZZES. Each quiz focuses on material from the 4-5 classes that most recently preceded the quiz (about 2.5 chapters in Sorrell). However, Chem 201 is a cumulative course. You should expect all quizzes to draw on material from all earlier parts of the course.

    Each quiz is administered twice, once as an in-class quiz and then immediately following that as a take-home quiz. The take-home version will be due 24 hours following the start of the in-class quiz, i.e., if you are in the WF section, your take-home will be due at 3:10 PM the next day, and if you are in the TuTh section, your take-home will be due at 10:30 AM the next day. The in-class and take-home versions of the quiz are identical, but different policies will govern how you take them and how they are graded. These policies are spelled out below.

    FINAL EXAM. The final exam covers the entire course: classes 1-25 + spectroscopic identification of molecular structures (Sorrell, chapters 13-14).

    Ground rules for all IN-CLASS quizzes & exams:

    • All in-class exams are closed book, homework, and notes.
    • Electronic devices, including listening devices (music players, cell phones, etc.) and calculators, are not permitted (see Model kits for iPad/iPhone/iPod exception).
      • Model kits. Students may bring a model kit to each exam. The instructor will also try to provide a small number of plastic models during the exam. Students may use a plastic model kit or they may use the iSpartan molecular modeling app (available for iPad, iPhone, and iPod touch), but exam use of iSpartan is limitedto sketching models, converting them to 3D, and rotating the models. You may not use the information buttons, change the appearance to space-filling or R/S, or perform conformation searches.
    • Data tables and charts, including the periodic table, are not permitted, except for those provided by the instructor (instructor-provided materials are limited to tables of characteristic IR/NMR spectroscopic parameters; periodic tables will not be provided.)
    • All work must be performed by each student working independently. You may not share answers, drawings, ideas, tables or models. Conversations are not allowed during the exam.
      • Honor note: the same in-class exams will be given to both lecture sections so the content of exams must not be discussed publicly until all students have completed the exams.
    • The exam must be taken during class in E314 unless special arrangements have been made with the instructor in advance.
    • Special accommodations will be made for students with documented needs. This documentation needs to be provided at least 48 hours in advance of the exam, and discussed with the instructor in person, so that the necessary arrangements can be made.
    • Academic honor system. All academic and laboratory work in Chem 201 is covered by Reed’s academic honor system. This means that all work that you present to the instructor (exams, homework, lab notebooks and reports, and so on) is understood to be 1) your own work, 2) work that has been completed under the ground rules established by the instructor, and 3) work that has been performed with full understanding of these ground rules. If questions arise in your mind as to the meaning of any ground rules, it is your responsibility to bring these questions to the instructor before you perform the work involved.

    Ground rules for all TAKE-HOME quizzes:

    • Take-home quizzes are optional. They are intended to give students who have trouble with recall, problem-solving, or test anxiety, a second-chance at demonstrating what they have learned. If you are happy with your performance on the in-class quiz, you can rest on that score (see Grading of take-home quizzes below).
    • Materials and information sources
      • You may refer to all of our class materials, including your textbook, solutions manual, and learning activities, and also your personal notes.
      • All other materials are off-limits. This includes web pages, library books, charts and tables (beyond those found in the ‘class materials’ listed above), books from the Chem student lounge/DoJo, and so on.
    • Group work
      • You may discuss problems and answers only with classmates from the same lecture session. This means WF students can work together and share ideas, drawings, answers. The same applies to TuTh students. Group work and sharing must not occur across different lecture sessions.
      • Because group work is limited to classmates, you may not discuss any part of a take-home quiz with tutors, DoJo staff, students from outside the course, or faculty not associated with Chem 201.
    • Due dates
      • As stated above, take-home quizzes are due 24 hours after the beginning of the class in which the in-class quiz was given. So, if you took a quiz during the W class, your take-home quiz is due Th at 3:10 PM.
      • Quizzes can be turned in to Kathy Kennedy, C303, or to Alan Shusterman, C408 (slide the quiz under our door if we are not present to receive the quiz). Take-home quizzes left in Eliot/Chem mailboxes or sent through the mail (US/campus) will not be accepted. Electronic copies of quizzes will not be accepted except in an emergency.
      • Because the quizzes are short (20-35 minutes in-class) and because accommodations are provided where needed on the in-class version, no time/space accommodations will be provided for the take-home version. You should have more than enough time to work on a take-home quiz and you are free to work on the quiz in any location/environment that suits your needs and is consistent with the policies outlined above.
    • Grading of take-home quizzes
      • Partial credit is routinely awarded where appropriate on in-class quizzes. As a rule, partial credit will not be awarded to answers on take-home quizzes. Take the time to make sure that your take-home answers are complete, carefully expressed, and correct to the best of your knowledge.
      • In-class and take-home quizzes will be scored separately. You will never be penalized for a low take-home quiz score. In other words,
        • If your take-home quiz earns a lower score than your in-class quiz, you will receive the score from the in-class quiz, i.e., the higher of the two scores.
        • If the take-home quiz receives a higher score than the in-class quiz, you will receive the score on the take-home quiz subject to one limitation: you can recover up to, but no more than, 50% of the points you lost on the in-class quiz. Examples:
          1. You earn 80% on the in-class quiz (20% lost) and 15% on the take-home quiz. Your score for this quiz will be 80%. You cannot receive a score lower than your in-class score.
          2. You earn 80% on the in-class quiz (20% lost) and 85% on the take-home quiz. Your score for this quiz will be 85%. In general, you will receive the higher of the two scores.
          3. You earn 70% on the in-class quiz (30% lost) and 90% on the take-home quiz. Your score for this quiz is only 85%. Although the higher quiz score is 90%, the maximum you can recover via the take-home is 15%, i.e., half of what was lost on the in-class quiz. 70 + 15 = 85%.

    Quiz & Exam schedule (tentative – changes will be announced in class & by email)


    Quiz #1 – T, 9/13 & W, 9/14 – covers classes 1-4 – answers
    Quiz #2 – T, 10/4 & W, 10/5 – emphasizes classes 5-9 (models especially useful here) – answers
    Quiz #3 – R, 10/27 & F, 10/28 – emphasizes classes 10-14 – answers
    Quiz #4 – T, 11/15 & W, 11/16 – emphasizes classes 15-19 – answers
    Quiz #5 – T, 12/6 & W, 12/7 – emphasizes classes 20-23 + NMR (Sorrell 13)* + IR (Sorrell 14.3)* – answers

    *NMR + IR will be covered in lab. Students who are enrolled in just the lecture portion of the class should attend selected lab sessions (contact Alan for more info)

    Final examFinals Week (Wed, Dec. 14, Vollum Lecture Hall, 6-9 pm) – (bring models) – covers classes 1-25 + NMR/IR + phenomena/theories employed in lab – answers

    Sample 2015 exams

    The following files provide blank exams from 2015 and exam answers.

    Quiz #1 – covered classes 1-4 (Ch. 1-2 partial) | answers
    Quiz #2 – covered classes 5-9 (Ch. 2-4) | answers
    Quiz #3 – covered classes 10-14 (Ch. 5-7 partial) | answers
    Quiz #4 – covered classes 15-19 (Ch. 7-9) | answers
    Quiz #5 – covered classes 20-23 + spectroscopy (Ch. 10-11, 13-14) | answers
    Final Exam – covered classes 1-25 + spectroscopy (Ch. 1-14) | answers

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