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Organic Chemistry I

Summer I 2019

Text:  www.ochem4free.info by Richard F. Daley & Sally J. Daley

Molecular models (either from the bookstore or from http://www.indigoinstruments.com, http://www.megamolecules.com, etc.) are allowed during exams but are not required.

Free organic chemistry drawing program for UTEP students:  ChemDraw.

A list of IUPAC nomenclature rules

A very nice NMR & IR site


Terms of Use:  You may not keep, redistribute, edit or link to the videos on this site.

I cannot guarantee video or audio for every lecture so please come to class!

Week Monday Tuesday Wednesday Thursday Friday
1-first hour June 10-Chapter 1-Video 11-Video 12-Video 13-Chapter 3-Video 14-Video
second hour Video Chapter 2-Video Video Video Chapter 4-Video
2-first hour 17-Review 1-Video 18-Exam 1 19-Chapter 5-Video 20-Video 21-Chapter 7-Video
second hour Video Video Video Chapter 6-Video Video
3-first hour 24-Review 2-Video 25-Exam 2-Video 26-Video 27-Video 28-Chapter 9-Video
second hour Video Chapter 8-Video Video Video Video
4-first hour July 1-Video 2-Exam 3 3-Video 4-Holiday-No Class! 5-Video
second hour Chapter 11-Video
Review 3 after class-Video
Video Chapter 10-Video Video
Review 4 after class-Video
5 July 8-Comprehensive Final 7-8:20 am,
Exam 4-8:25-9:45
July 9-Exam 4 Homework Due at 5 pm!      
Exam 1: Chapters 1-3
Exam 2: Chapters 4-6
Exam 3: Chapters 7-8
Exam 4: Chapters 9-11

Your grade for this course will consist of:

  1. the three best out of four regular 1 hour exams, 3 x 100 points. 
  2. comprehensive final, 100 points.
  3. exercises, 100 points

for a total of 500 points, A > 89.5 %, B > 79.5 %, C > 69.5 %, D > 59.5 % of these points.


  1. Clean un-mutilated scan-tron forms, #2 pencils and your UTEP ID are required for each exam.
  2. The scan-tron form will be your final in-class exam grade.
  3. Exam dates are tentative and subject to change!
  4. No makeup exams because everyone has the opportunity to drop one regular exam (not the final)!
  5. If you miss more than one exam you have greater concerns than this course and you should drop the course before you earn an "F". 
  6. Students are responsible for dropping from the course before the university drop deadline.  Per university policy, I cannot drop students after this deadline.
  7. If I suspect that you are cheating on an exam, I will recommend to the Dean of Students that the particular exam in question be dropped from your average.  The Dean of Students may suggest additional rehabilitation measures.
  8. No cell phones, audio equipment or caps during exams.

Exam Homework:

  1. Exams 1-4 may be assigned as homework if the class average is below 75 % on a particular in-class exam.
  2. The in-class exam and exam homework will be averaged to come up with your grade for a particular exam.
  3. Students are encouraged to work together on this homework but shall not consult with anyone else outside this class including the lecturer.
  4. Your exam grade will not go down if your exam homework is lower than your in-class exam grade.
  5. Always write your answers on your exam sheets so that you can do the homework and check your answers against the key.
  6. The Exams as homework will be submitted through http://organic.utep.edu/quiz on time, no excuses since the process is automated.
  7. The Exam key will be provided through http://organic.utep.edu/quiz after the Exam as homework due date and time.

Extra Credit:

  1. Extra credit will be used if the class average is below 75%. 
  2. The extra credit will consist of answering lecture questions via a laptop, tablet or phone.
  3. Please do not use your device to get distracted doing other things in class, e.g., videos, email, etc.
  4. Help for setting up wireless device can be found at http://wireless.utep.edu
  5. Twice as much credit will be given for correct over incorrect answers.
  6. Survey questions will not be graded and thus will receive only half credit.
  7. The extra-credit feedback will always be behind one graded answer. 
  8. The extra credit will not raise the class average above 75 %.
  9. The extra credit will be scaled to make the class average 75 %. 
  10. Because of the numerous opportunities to do well in this course and the extra credit, the grading scale will not change.
  11. If by random attendance you are found not to be answering extra-credit questions yourself, your extra credit account will be turned-off.
  12. I reserve the right to disregard answers that do not make sense to what is asked.


  1. It is your responsibility to attend every lecture (I reserve the right to use attendance as part of your grade!) and do as many problems possible from the chapters we cover.
  2. No excuses for missing exams or not completing exercises on time!  This course is your full-time job!
  3. This semester's automatic "W" drop deadline is ?  Because of the policy on the number of drops a students can have, please talk directly to the College of Science about dropping this course after this deadline.

Please look at the undergraduate catalog for policies pertaining to everything else.

Study Suggestions:

  1. Read before lecture but do not reread to the point of frustration.  Read to familiarize yourself with the location of subjects in each chapter.  Keep in mind that science textbooks are technical manuals not "easy reading".
  2. Do problems.  In fact do a section of problems without looking at the key and grade yourself  honestly.  If after you peek at the key you say "I could have gotten that", this is not a good indication that you will do well on an exam.  Look back only at those sections of the text that pertain to a problem to optimize your study time.
  3. It is not a bad idea or cheating to look at your textbook, notes, work with a friend, or ask your instructor for help on the exercises.  In fact I have no control how students do the exercises.  The exercises are really tutorials and not quizzes.  If after you get your 100 % you do not go back and do a particular exercise on your own, you are cheating yourself of the opportunity to evaluate yourself honestly.  Remember that you can repeat an exercise as many times as you like for the highest score before its due date and time.  Try to do the exercise days and not minutes before it is due so you can ask for some help.  Remember that it is the time you finish the lesson and the server's time that counts!


Exercises Due Dates

(All lessons and mechanisms due on the midnight (SMT) of the date given).

L# or M#


Video "Rosetta Stone"
Suggested Reading
Pages (Sections)
Due Date
L1 Normal or n-Alkanes Ö 79-81 (2.4-2.5) Sunday, June 16
L2 Iso and Neo Common Names Ö 72-79 (2.1-2.3)
L3 Common Names of Alkyl Radicals Ö 90-95 (2.7)
L4 Systematic Names of Alkyl Radicals Ö 95-97 (2.7)
L5 Branched Acyclic Alkanes: Systematic Nomenclature Ö 81-87(2.5)
L6 Smallest Example of a Functional Group Ö 97-100 (2.8)
L7 Cis and Trans on Monocyclic Alkanes Ö 146-156 (3.9-3.10)
L8 Mono Cyclic Alkanes Ö 87-90, 134-146, 156-159 (2.6, 3.5-3.8, 3.11)
L9 Cis and Trans on Bicyclic Alkanes:  Von-Baeyer Nomenclature Ö 159-167 (3.12-3.13) Sunday, June 23
L10 Endo, Exo, Syn and Anti on Bicyclic Alkanes Ö 839-846 (16.6)
L11 Acyclic Alkenes:  E-Z Nomenclature Ö 100-109,  678-679 (2.9-2.10, 13.7)
L12 Mono Cyclic Alkenes Ö 165 (3.13)
L13 Acyclic Alkanes with one Chiral Center:  R, S Nomenclature Ö 540-545 (11.2)
L14 Acyclic Alkanes with two or more Chiral Centers Ö 555-560 (11)
L15 Alkanes Review Ö
L16 Line Notation Ö 74 (2.1)
Physical Properties (4)
  Equilibrium of Acid Base Reactions   (5)  
L17 Acyclic Alcohols Ö 581-588 (12.1) Sunday, June 30
L18 Acyclic Aldehydes and Ketones Ö 298-300 (7.1)
M1 Mechanism:  The acid catalyzed synthesis of the ketal of cyclohexanone and ethane-1,2-diol Ö 310-319 (7.5)
M2 Mechanism:  The acid catalyzed synthesis of the enol ether of 3-methylbutanone and methanol   310-319 (7.5)
L19 Hydrates, Hemiacetals, Hemiketals, Acetals, Ketals, Enols, Enolates, Enol Ethers and Oxoniums Ö 310-319 (7.5)
L20 Imines, Enamines, Hydrazones, and Oximes Ö 319-324 (7.6)
M3 Mechanism:  The synthesis of the enamine of 2,2-dimethylcyclohexanone and pyrrolidine   319-324 (7.6)
M4 Mechanism:  The synthesis of triethylamine by reductive amination   319-324 (7.6)
L21 Reductive Addition to Aldehydes and Ketones Ö 326-338 (7.7-7.8)
M5 Mechanism:  The synthesis of pentan-3-ol from bromoethane and propanal   326-338 (7.7-7.8)
L22 The Wittig Reaction Ö 341-347 (7.10)
L23 Carboxylic Acids:  Common and Systematic Nomenclature Ö 300-303 (7.1)
M6 Mechanism: The Wittig reaction of iodomethane and cyclohexanone (#Ring Pi Electrons = 18)   341-347 (7.10)
M7 Mechanism: The synthesis of caprolactone by the acid catalyzed Fischer esterification of 6-hydroxyhexanoic acid   359-382, 399-402 (8.1-8.4, 8.7)
M8 Mechanism:  The reaction of propanoic acid and methanamine with DCC   1209 -1216 (23.6)
L24 Synthesis of Carboxylic Acid Derivatives from Carboxylic Acids Ö 359-382, 399-402 (8.1-8.4, 8.7)
M9 Mechanism:  The reduction of N,N-diethylethanamide with diisobutylaluminum hydride   382-391(8.5)
L25 Reduction of Carboxylic Acid Derivatives Ö 382-399 , 402-404 (8.5-8.6, 8.7)
M10 Mechanism:  The reduction of methyl propanoate with methyl magnesium chloride and hydronium workup   391-399 (8.6)
L26 Acyclic Alkyl Halides Ö (2) Saturday, July 6
L27 Acyclic Thiols Ö 581-588 (12.1)
L28 Amines and Ammonium Salts Ö 581-588 (12.1)
L29 Acyclic Ethers Ö 581-588 (12.1)
L30 IR of C4H8O2 Isomers Ö 436-461 (9.2-9.8)
L31 1H NMR of C6H14O Isomers Ö (10)
L32 13C NMR of Acyclic Alkanes Ö (10)




jsal at utep dot edu

PSCI 203C, 308

Telephone: (915) 747-5704

Office Hours: MF 10:30 am to noon or by appointment in PSCI 203C or 308