Teaching Guides Query



Academic Year: 2024/25

592 -

18870 - ORGANIC CHEMISTRY

This is a non-sworn machine translation intended to provide students with general information about the course. As the translation from Spanish to English has not been post-edited, it may be inaccurate and potentially contain errors. We do not accept any liability for errors of this kind. The course guides for the subjects taught in English have been translated by their teaching teams


Teaching Plan Information

Code - Course title:
18870 - ORGANIC CHEMISTRY
Degree:
592 -
Faculty:
104 - Facultad de Ciencias
Academic year:
2024/25

1. Course details

1.1. Content area

ORGANIC CHEMISTRY

1.2. Course nature

Optional

1.3. Course level

Grado

1.4. Year of study

XX

1.5. Semester

First semester

1.6. ECTS Credit allotment

6.0

1.7. Language of instruction

English

1.8. Prerequisites

BU students must have taken at least one of the following options:

 

Option 1: CH101 (General Chemistry 1) and CH102 (General Chemistry 2).

Option 2: CH101 (General Chemistry 1) and CH110 (General and Quantitative Analytical Chemistry).

Option 3: CH111 (Intensive General and Quantitative Analytical Chemistry 1) and CH112 (Intensive General and Quantitative Analytical Chemistry 2).

 

UAM students must have taken any of the following courses:

 

16476 (Química -Grado en Ciencias Ambientales-)

16535 (Química -Grado en Ingeniería Química-)

16575 (Química -Grado en Ciencias de la Alimentación-)

18201 (Química -Grado en Bioquímica-)

18422 (Química General –Grado en Nutrición, Biología o Física-)

1.9. Recommendations

-

1.10. Minimum attendance requirement

Attendance to classes is strongly recommended. We hope that all students will remain healthy throughout the semester and are able to fully engage and participate in the course. If you did unfortunately become ill, we require that you follow the protocols mandated by the University under those circumstances. The course attendance and engagement policies already reflect substantial flexibility to allow for absences of short to moderate length due to illness. Please make sure to contact your instructor immediately about any absences. In the case of a prolonged illness that is not already covered by the course absence policies, we will work with the CAS Dean's office to determine the best course of action for any given student. To receive full credit a student must document the reason for their absence (for example a signed and stamped doctor’s note). Please note that having scheduled exams in another subject is not a valid excuse. Attendance to seminars courses is mandatory; absences must be justified and will be analyzed for each particular case.

Students must always attend their own scheduled lab session. Punctuality is crucial as special instructions may be given at the start of the lab. Attendance will be taken at the start of the lab, if you are 5 minutes or more late to your lab section, you will be asked to leave. Lab is an integral part of the course. Anyone not completing the laboratory portion of the course will receive a failing grade in the course.

1.11. Subject coordinator

Ramon Jesus Gomez Arrayas

1.12. Competences and learning outcomes

1.12.1. Competences / Results of the training and learning outcomes

-

1.12.2. Learning outcomes

Outcome 1 – Core Concepts and Theoretical Tools in Quantitative Reasoning. This will be particularly prominent in understanding spectroscopy, as well in the laboratory wherein molar equivalency, concentrations, and yield calculations are critical. Understanding stoichiometry of organic reactions also requires quantitative reasoning, as due the balance of kinetics and thermodynamics, particularly as they apply to reaction outcome (kinetic vs thermodynamic control). Kind of mirrors life in the sense of impulsive reactions (kinetics) vs long term reasoning (thermodynamics).

Outcome 2 – Interpretation of Quantitative Models. This outcome is especially important in spectral interpretation. Students will learn how spectroscopic adsorption of energy from the electromagnetic spectrum (i.e. how molecules interact with these energies) are signatures of specific structural features, and hence can be used to deduce structures. For kinetics vs thermodynamics - reaction coordinate diagrams are a commonly employed graphic representation that students will learn. Accurate drawing of molecular structures is also critical.

Outcome 3 – Communication of Quantitative Information. This outcome will be relevant in the lab reports the students write for each lab experiment. Students will also learn to present reaction mechanisms in a meaningful manner.

Outcome 4 – Recognize and Articulate Capacity and Limitations. Understanding the origin of experimental error, and what is reasonable error, and what is not, is always a component of the laboratory experience. Students will understand what is acceptable variation, and what is not. Especially emphasized is the understanding of significant figures.

1.12.3. Course objectives

TIFICACION y CAMBIO EN LA GUIA) Esta sección debe quedar del siguiente modo:

The primary goal of this course is to learn the fundamental principles of organic chemistry while developing analytical skills to think about solutions to organic chemistry problems. In this class, the emphasis will be on organic structure and the consequences of structure, reactivity, and reaction mechanisms.

Units and Tools

Scientific Inquiry: Students will identify and apply the major concepts of organic chemistry to explain phenomena in the biological and material world, and devise applications of organic chemistry for addressing real-world needs. This includes introductions to the way that scientists explain complex systems such as living organisms, drug discovery, polymer design, and explore the fundamental organic chemistry that lies behind the preparation, structure, and other characterization of important organic molecules.

These fundamentals will enable the understanding of more complex systems in biochemistry, strategies in drug discovery, polymer design, and explore the fundamental organic chemistry that lies behind the preparation, structure, and other characterization of important organic molecules. Students will probe deeply into the physical basis of organic chemistry-based phenomena.

Quantitative Reasoning. Many fundamental principles of organic chemistry are based on the laws of physics, which can be expressed mathematically. Students will learn how to apply these laws, both in lecture and in the laboratory, for quantitative explanation of observations, and also to make quantitative predictions as applied to reaction kinetics, thermodynamics, spectroscopy, stoichiometry and catalysis.

Important learning goals that the student will wish to achieve are:

(1) Understanding the implications of the covalent bond in the structure of organic compounds

(2) Learning how to name organic compounds systematically

(3) Ability to deduce the structures of organic molecules by interpreting their nuclear magnetic resonance spectra

(4) Developing an appreciation for the interplay of an organic molecule’s three-dimensional structure and that molecule’s chemical properties

(5) Ability to predict the properties and reactivity of organic compounds

 

1.13. Course contents

 

Lecture contents and tentative schedule:

 

Week # /Date

Lecture topics

End of chapter questions

1

Sept

Intro 1.1-1.2

Shorthand Notation 1.12

Dash/Wedge Notation 2.2

Lewis Structures/Formal Charge 1.5-1.6, 1.9 Polar covalent bonds 1.7

Resonance structures 1.10-1.11 Functional Groups Ch 1.13

 

Not covered in lecture but review: Ch 1.3-1.4, 1.8

Ch 1.1-1.41

2

Sept

Nomenclature of Alkanes A.1-A.7 Naming of Alkenes and Alkynes B.1-B.2 VSEPR Theory 2.1

Valence Bond Theory and MO Theory: 3.1-3.11 Hybridization and Resonance

Acyclic conformational analysis 4.1-4.3

 

Read on your own: 2.3, 2.4

A.19-1.22, A.24, 2.1-2.13, B.9,

B.14, Ch. 3.1-3.15, 3.20, 3.21,

3.23, 3.24, 3.41, 3.43, 4.1-4.11

3

Sept

Ring Strain 4.3

Conformers: Cyclohexane and chair flips 4.5 Substituted cyclohexanes: 4.7-4.9

Constitutional isomers 4.10-4.12 Defining Configurational Isomers 5.1

Diastereomers: Double bond configurations 3.7/5.8

 

Ch 5.1-5.16

4

Oct

Enantiomers 5.2-5.3

Chirality 5.4

Chiral Centers 5.5

R/S 5.6

Mid-Term-Exam 1 Review

 

Mid-Term-Exam 1

Ch 5.1-5.16

5

Oct

Drawing Stereoisomers 5.9 Examples

Physical and Chemical Properties 5.12 Separating Configurational Isomers 5.13 Optical Activity 5.14

Chirality of Biomolecules 5.15-5.16 Intro to NMR 17.1-17.2

NMR: Unique signals, shielding 17.3 Time scale of NMR 17.4

Chemical Shift: 17.5 Predicting chemical shift 17.6 Integration 17.8

Ch, 5.43-5.51, 5.54, 5.57, 5.58,

5.60, 5.61, 5.64-5.66

Ch. 17.1 (a, d-i), 17.2-17.12,

17.20-17.22

6

Oct

Monday, holiday, Substitute Monday on Tuesday, October 11. All Tuesday classes canceled.

Simple splitting 17.9

Coupling Constants and Complex Splitting 17.10 Signal Resolution 17.11

Diastereotopic protons

Elucidating molecular structure from NMR 17.14

Ch. 17.23-28, 17.36-17.49

7

Oct

Introduction to Reaction Mechanisms 6.1

Proton Transfer Outcomes 6.2

Chemical Equilibrium 6.3 Gibbs Free Energy 6.4-6.5

Functional Groups and Acidity 6.6

Relative strengths of charged and uncharged acids 6.7

Ch 6.1-6.8, 6.12, 6.15-6.28

8

Nov

Relative Acidities of Protons on Atoms with like Charges 6.8

Strategies for Ranking Acids and Bases 6.9

Electron Donating and Withdrawing groups Mechanism: proton transfer 7.1

Electrophiles/Nucleophiles

Mid-Term-Exam 2 Review

 

Mid-Term-Exam 2

Ch. 6.29-6.42, 6.49-6.67

9

Nov

SN2 Mechanism 7.2

Bond breaking and making 7.3

Nucleophilic Addition/Elimination 7.4

E2 Mechanism 7.5

Electrophilic Addition/Elimination 7.6

Carbocation Rearrangements 7.7

Driving Force for Chemical Reactions 7.8

Carbocations and charge stability 7.9

MO Theory behind Chemical Reactions C.1-2

Reasonableness of a Mechanism 8.6

SN1 Mechanism 8.1

SN2 Mechanism Revisited

Ch. 7.1-7.15 Ch.7.16-7.39, C.1- C.9

10

Nov

E1 Mechanism 8.2

E2 Mechanism Revisited Kinetics 8.3-8.4

Stereochemistry 8.5

 

 

Ch. 8.1-8.48

11

Nov

Resonance-Delocalized intermediates 8.7

Competition between SN2, SN1, E2 and E1 9.1-9.12

Reactions of Alcohols and Strong Acid

Mid-Term-Exam 3 Review

 

Mid-Term-Exam 3

Ch. 9.1-9.37, 9.42-9.50

12

Dec

LABORATORY SESSIONS

 

LAB-Exam

 

13

Dec

Organic Synthesis 10.1-10.3

Ether Formation 10.4

Formation of Epoxides by Nucleophilic Substitution 10.8

Amines and Quaternary Ammonium salts from Alkyne alkylation

Alkylation of Alpha carbon 11.4 Epoxides as substrates 10.7

Opening of Epoxides with carbon nucleophiles 11.2

Converting Alcohols to alkyl halides 10.5 Halogenation of Alpha carbons 10.6

Ch. 10.1-10.59, 11

Ch. 11.9-11.15, 11.27-11.32

14

Dec

Synthetic traps 11.4

Strategies for Success in Synthesis 11.5

 

FINAL EXAM Review

FINAL EXAM

Ch. 11.1-11.8, 11.16-11.19,

11.34-11.40

 

 

Experimental techniques:

• Acid-base extraction using a separatory funnel.

• Thin-Layer-Chromatography (TLC).

• Purification techniques: column chromatography, recrystallization & distillation

• Enantiomeric purity and specific optical rotation values.

• Use of a rotary evaporator.

• Filtration methods

• Synthesis using a reflux apparatus.

1.14. Course bibliography

Required materials:

  1. Textbook: Karty, Joel; Organic Chemistry Principles and Mechanisms, 3rd ed. Norton Publishing.
  2. Introduction to Organic Laboratory Techniques. A Microscale Approach, 3rd Ed. – BU custom edition, W.B. Saunders, 2000.
  3. Molecular models (optional, highly suggested): Many suitable styles (e.g., space-filling, ball-and-stick, framework) are available. Recommended: Duluth’s MM-005 set.
  4. Lab coat, notebook and safety goggles (for laboratory sessions).

 

2. Teaching-and-learning methodologies and student workload

2.1. Contact hours

Office hours will be arranged upon request

2.2. List of training activities

LECTURES. Before you come to lecture you are expected to complete a carefully reading of the sections from the text. This allows you to review material you might already know. You will also have an idea about what material is coming. You will know what information is in the book - and you won't have to write it all down in class. You may even be able to generate a few questions. You can pay special attention to any unclear parts during lecture. In-class tests of quizzes about the topic of the lecture can be given by teachers to students in seminar sessions with or without prior notice.

It is also recommended that you do practice questions/problems from the text and lectures. These questions serve to reinforce concepts learned in lecture and from reading the text. They also show how those concepts can be applied to problems. As such, they will help to prepare you for the in-class tests and final exam.

SEMINARS/DISCUSSION SECTIONS. Studying organic chemistry means doing problems. The students will be given a problem set (seminar worksheets) homework assignment and asked to apply the concepts provided in the text and lectures in ways other than the text or lecture do. Organic chemistry involves a problem-solving method that many of you may not have seen before. The unique feature of OC problems is that sometimes the problems can be solved forwards; sometimes they have to be solved backwards! Sometimes there is no single way to solve a problem; often solving Organic Chemistry problems is a challenge! However, while working on the problems, you will learn how to organize a lot of sometimes seemingly disparate pieces of information and figure out which one you need. You do not have to memorize concepts, working on the problems you became familiar with these concepts by using them and understanding their context.  If you can learn to do organic chemistry, you will acquire valuable problem-solving skills.

The assigned problems will serve as the primary focus of the discussion sessions. During the discussion sessions, the instructor and students discuss about problem-solving strategies to improve student capabilities. All students will participate in the scheduled discussion section. Do not look at the answer until you have given the problem a serious try. Work the in-chapter problems pertaining to the assigned sections in the text, do as many end-of-chapter problems needed to gain mastery of the material. Some of the end of the chapter questions will be on your exams.

Recall that there is also mandatory homework due every week.

Attendance is mandatory. Students are expected to arrive on time and to actively participate in all of the lecture and discussion sections. A portion of your course grade will be awarded based on your discussion work, including (on-time) attendance and engagement (in group work and class-wide exercises) in discussion. If you actively and consistently participate in lectures and seminars, if your grade in the class is on a grade border you will be boosted to the higher grade. Working on homework assignments during discussion is not allowed.

HELP OUTSIDE OF CLASS. Please, arrange a meeting and come to office hours. Please keep current with the lecture material: cramming the night before an exam usually fails to produce adequate results because most students cannot effectively absorb the subject matter in a short amount of time.

CONCERNS. If you are experiencing difficulty, please contact your course instructor without delay. If dropping the course appears to be in your best interest, we still would like to work through the decision with you. We are also happy to advise you on appropriate choices for your academic program.

 

LAB ASSIGNMENTS:

1) Prelab Questions. Prelab questions for each lab can be found on LAB MANUAL before the procedure. These questions must be answered before you come to lab.

2) Lab Notebook. A most important skill is the ability to record clearly the phenomena observed in the course of the experiment since these frequently are a sign of important chemical events. Examples of observations to be noted are color changes, the evolution of heat, the liberation of gas, the physical state and appearance of starting materials, intermediate reaction mixtures, and crude and purified products, etc. Set up your lab notebook so that observations can be recorded on the same page as the portion of the experimental procedure which is being observed. Data will be largely quantitative in nature and should be recorded with appropriate units. Examples include melting and boiling point ranges, quantities of materials used and products obtained, percent yields, reaction times, spectroscopic absorption maxima, Rf values, retention times, etc. All information should be recorded in your lab notebook.

3) Post-lab questions. (results/discussion/spectral data).

 

Activity

# hours

Lectures

50

Seminars/practical sessions

20

Laboratory

25

Exams

10

Office hous

5

 

3. Evaluation procedures and weight of components in the final grade

3.1. Regular assessment

 

  • MID-TERM EXAMS (MTE): Three 80-minute exams are administered along the course (location to be announced at least two weeks in advance) in additional time to the lecture meeting time. All MTE are cumulative. MTE are graded on a 10-point basis. Your lowest MTE score will be assigned a lower percentage to the final grade. No make-up lecture exams are given for any reason (only in exceptional circumstances); please do not ask to take a make-up lecture exam nor ask to take a lecture exam at other than the scheduled date and time. Do not make travel plans that conflict with the lecture exams.
  • IN-CLASS TESTS OF QUIZZES. Four 15-20 minute in-class tests with a problem about the topic of the lecture will be given by teachers to students in some seminar sessions along the course. All in-class tests are cumulative and graded on a 10-point basis. Your lowest in-class test score will be dropped in calculating your course grade.
  • FINAL EXAM (FE): A cumulative 2.5-3-hour final exam will be administered at the end of the course (exact time and location to be announced at least two weeks in advance). FE is graded on a 10-point basis.

There are no make-up exams whatsoever. Incomplete grades are not accepted in this abroad program, as you will be leaving the site at the end of the semester.

3.1.1. List of evaluation activities

 

Evaluable activity

Percentage

MTE

15%

MTE

15%

MTE (lowest score)

7.5%

FE

40%

IN-CLASS TESTS

7.5%

LABORATORY

15%

 

Course grades are calculated by the following formula:

CH203 Grade = MTE · 0.15 + MTE · 0.15 + MTE · 0.075 (lowest score)+ FE · 0.4 + In-class test · 0.075 + Lab ·0.15

where MTE1 andMTE2 are the scores of your two highest of three MID-TERM-EXAMS, FE is the score of your FINAL EXAM, SEMINARS is the score of seminars and discussion sessions, and LABORATORY is your lab score. All individual scores are based on 10 points. The maximum score is 10. The minimum score to pass is 5.0.

Spanish grade ranges are:

  • Lowest (no pass): 0-4,9: Suspenso (SS).
  • Fair (pass): 5,0-6,9: Aprobado (AP).
  • Intermediate-High: 7,0-8,9: Notable (NT).
  • Highest: 9,0-10: Sobresaliente (SB).

There are no extra-credit projects to offset poor performance on exams/seminars. Please do not ask to have the course grade you earn raised gratuitously because you fail to satisfy the GPA requirements of your program of study, scholarship, etc.

3.2. Resit

 

 

3.2.1. List of evaluation activities

-

4. Proposed workplan

-


Curso Académico: 2024/25

592 - Asignaturas transversales

18870 - ORGANIC CHEMISTRY


Información del Plan Docente

Código - Nombre:
18870 - ORGANIC CHEMISTRY
Titulación:
592 - Asignaturas transversales
Centro:
104 - Facultad de Ciencias
Curso Académico:
2024/25

1. Detalles de la asignatura

1.1. Materia

-

1.2. Carácter

Optativa

1.3. Nivel

Grado

1.4. Curso

XX

1.5. Semestre

Primer semestre

1.6. Número de créditos ECTS

6.0

1.7. Idioma

English

1.8. Requisitos previos

-

1.9. Recomendaciones

-

1.10. Requisitos mínimos de asistencia

Attendance to classes is strongly recommended. We hope that all students will remain healthy throughout the semester and are able to fully engage and participate in the course. If you did unfortunately become ill, we require that you follow the protocols mandated by the University under those circumstances. The course attendance and engagement policies already reflect substantial flexibility to allow for absences of short to moderate length due to illness. Please make sure to contact your instructor immediately about any absences. In the case of a prolonged illness that is not already covered by the course absence policies, we will work with the CAS Dean's office to determine the best course of action for any given student. To receive full credit a student must document the reason for their absence (for example a signed and stamped doctor’s note). Please note that having scheduled exams in another subject is not a valid excuse. Attendance to seminars courses is mandatory; absences must be justified and will be analyzed for each particular case.

Students must always attend their own scheduled lab session. Punctuality is crucial as special instructions may be given at the start of the lab. Attendance will be taken at the start of the lab, if you are 5 minutes or more late to your lab section, you will be asked to leave. Lab is an integral part of the course. Anyone not completing the laboratory portion of the course will receive a failing grade in the course.

1.11. Coordinador/a de la asignatura

Ramon Jesus Gomez Arrayas

1.12. Competencias y resultados del aprendizaje

1.12.1. Competencias / Resultados del proceso de formación y aprendizaje

-

1.12.2. Resultados de aprendizaje

Outcome 1 – Core Concepts and Theoretical Tools in Quantitative Reasoning. This will be particularly prominent in understanding spectroscopy, as well in the laboratory wherein molar equivalency, concentrations, and yield calculations are critical. Understanding stoichiometry of organic reactions also requires quantitative reasoning, as due the balance of kinetics and thermodynamics, particularly as they apply to reaction outcome (kinetic vs thermodynamic control). Kind of mirrors life in the sense of impulsive reactions (kinetics) vs long term reasoning (thermodynamics).

Outcome 2 – Interpretation of Quantitative Models. This outcome is especially important in spectral interpretation. Students will learn how spectroscopic adsorption of energy from the electromagnetic spectrum (i.e. how molecules interact with these energies) are signatures of specific structural features, and hence can be used to deduce structures. For kinetics vs thermodynamics - reaction coordinate diagrams are a commonly employed graphic representation that students will learn. Accurate drawing of molecular structures is also critical.

Outcome 3 – Communication of Quantitative Information. This outcome will be relevant in the lab reports the students write for each lab experiment. Students will also learn to present reaction mechanisms in a meaningful manner.

Outcome 4 – Recognize and Articulate Capacity and Limitations. Understanding the origin of experimental error, and what is reasonable error, and what is not, is always a component of the laboratory experience. Students will understand what is acceptable variation, and what is not. Especially emphasized is the understanding of significant figures.

1.12.3. Objetivos de la asignatura

The primary goal of this course is to learn the fundamental principles of organic chemistry while developing analytical skills to think about solutions to organic chemistry problems. In this class, the emphasis will be on organic structure and the consequences of structure, reactivity, and reaction mechanisms.

Units and Tools

Scientific Inquiry: Students will identify and apply the major concepts of organic chemistry to explain phenomena in the biological and material world, and devise applications of organic chemistry for addressing real-world needs. This includes introductions to the way that scientists explain complex systems such as living organisms, drug discovery, polymer design, and explore the fundamental organic chemistry that lies behind the preparation, structure, and other characterization of important organic molecules.

These fundamentals will enable the understanding of more complex systems in biochemistry, strategies in drug discovery, polymer design, and explore the fundamental organic chemistry that lies behind the preparation, structure, and other characterization of important organic molecules. Students will probe deeply into the physical basis of organic chemistry-based phenomena.

Quantitative Reasoning. Many fundamental principles of organic chemistry are based on the laws of physics, which can be expressed mathematically. Students will learn how to apply these laws, both in lecture and in the laboratory, for quantitative explanation of observations, and also to make quantitative predictions as applied to reaction kinetics, thermodynamics, spectroscopy, stoichiometry and catalysis.

Important learning goals that the student will wish to achieve are:

(1) Understanding the implications of the covalent bond in the structure of organic compounds

(2) Learning how to name organic compounds systematically

(3) Ability to deduce the structures of organic molecules by interpreting their nuclear magnetic resonance spectra

(4) Developing an appreciation for the interplay of an organic molecule’s three-dimensional structure and that molecule’s chemical properties

(5) Ability to predict the properties and reactivity of organic compounds

 

1.13. Contenidos del programa

Lecture contents and tentative schedule:

 

Week # /Date

Lecture topics

End of chapter questions

1

Sept

Intro 1.1-1.2

Shorthand Notation 1.12

Dash/Wedge Notation 2.2

Lewis Structures/Formal Charge 1.5-1.6, 1.9 Polar covalent bonds 1.7

Resonance structures 1.10-1.11 Functional Groups Ch 1.13

 

Not covered in lecture but review: Ch 1.3-1.4, 1.8

Ch 1.1-1.41

2

Sept

Nomenclature of Alkanes A.1-A.7 Naming of Alkenes and Alkynes B.1-B.2 VSEPR Theory 2.1

Valence Bond Theory and MO Theory: 3.1-3.11 Hybridization and Resonance

Acyclic conformational analysis 4.1-4.3

 

Read on your own: 2.3, 2.4

A.19-1.22, A.24, 2.1-2.13, B.9,

B.14, Ch. 3.1-3.15, 3.20, 3.21,

3.23, 3.24, 3.41, 3.43, 4.1-4.11

3

Sept

Ring Strain 4.3

Conformers: Cyclohexane and chair flips 4.5 Substituted cyclohexanes: 4.7-4.9

Constitutional isomers 4.10-4.12 Defining Configurational Isomers 5.1

Diastereomers: Double bond configurations 3.7/5.8

 

Ch 5.1-5.16

4

Oct

Enantiomers 5.2-5.3

Chirality 5.4

Chiral Centers 5.5

R/S 5.6

Mid-Term-Exam 1 Review

 

Mid-Term-Exam 1

Ch 5.1-5.16

5

Oct

Drawing Stereoisomers 5.9 Examples

Physical and Chemical Properties 5.12 Separating Configurational Isomers 5.13 Optical Activity 5.14

Chirality of Biomolecules 5.15-5.16 Intro to NMR 17.1-17.2

NMR: Unique signals, shielding 17.3 Time scale of NMR 17.4

Chemical Shift: 17.5 Predicting chemical shift 17.6 Integration 17.8

Ch, 5.43-5.51, 5.54, 5.57, 5.58,

5.60, 5.61, 5.64-5.66

Ch. 17.1 (a, d-i), 17.2-17.12,

17.20-17.22

6

Oct

Monday, holiday, Substitute Monday on Tuesday, October 11. All Tuesday classes canceled.

Simple splitting 17.9

Coupling Constants and Complex Splitting 17.10 Signal Resolution 17.11

Diastereotopic protons

Elucidating molecular structure from NMR 17.14

Ch. 17.23-28, 17.36-17.49

7

Oct

Introduction to Reaction Mechanisms 6.1

Proton Transfer Outcomes 6.2

Chemical Equilibrium 6.3 Gibbs Free Energy 6.4-6.5

Functional Groups and Acidity 6.6

Relative strengths of charged and uncharged acids 6.7

Ch 6.1-6.8, 6.12, 6.15-6.28

8

Nov

Relative Acidities of Protons on Atoms with like Charges 6.8

Strategies for Ranking Acids and Bases 6.9

Electron Donating and Withdrawing groups Mechanism: proton transfer 7.1

Electrophiles/Nucleophiles

Mid-Term-Exam 2 Review

 

Mid-Term-Exam 2

Ch. 6.29-6.42, 6.49-6.67

9

Nov

SN2 Mechanism 7.2

Bond breaking and making 7.3

Nucleophilic Addition/Elimination 7.4

E2 Mechanism 7.5

Electrophilic Addition/Elimination 7.6

Carbocation Rearrangements 7.7

Driving Force for Chemical Reactions 7.8

Carbocations and charge stability 7.9

MO Theory behind Chemical Reactions C.1-2

Reasonableness of a Mechanism 8.6

SN1 Mechanism 8.1

SN2 Mechanism Revisited

Ch. 7.1-7.15 Ch.7.16-7.39, C.1- C.9

10

Nov

E1 Mechanism 8.2

E2 Mechanism Revisited Kinetics 8.3-8.4

Stereochemistry 8.5

 

 

Ch. 8.1-8.48

11

Nov

Resonance-Delocalized intermediates 8.7

Competition between SN2, SN1, E2 and E1 9.1-9.12

Reactions of Alcohols and Strong Acid

Mid-Term-Exam 3 Review

 

Mid-Term-Exam 3

Ch. 9.1-9.37, 9.42-9.50

12

Dec

LABORATORY SESSIONS

 

LAB-Exam

 

13

Dec

Organic Synthesis 10.1-10.3

Ether Formation 10.4

Formation of Epoxides by Nucleophilic Substitution 10.8

Amines and Quaternary Ammonium salts from Alkyne alkylation

Alkylation of Alpha carbon 11.4 Epoxides as substrates 10.7

Opening of Epoxides with carbon nucleophiles 11.2

Converting Alcohols to alkyl halides 10.5 Halogenation of Alpha carbons 10.6

Ch. 10.1-10.59, 11

Ch. 11.9-11.15, 11.27-11.32

14

Dec

Synthetic traps 11.4

Strategies for Success in Synthesis 11.5

 

FINAL EXAM Review

FINAL EXAM

Ch. 11.1-11.8, 11.16-11.19,

11.34-11.40

 

 

Experimental techniques:

• Acid-base extraction using a separatory funnel.

• Thin-Layer-Chromatography (TLC).

• Purification techniques: column chromatography, recrystallization & distillation

• Enantiomeric purity and specific optical rotation values.

• Use of a rotary evaporator.

• Filtration methods

• Synthesis using a reflux apparatus.

 

1.14. Referencias de consulta

Required materials:

  1. Textbook: Karty, Joel; Organic Chemistry Principles and Mechanisms, 3rd ed. Norton Publishing.
  2. Introduction to Organic Laboratory Techniques. A Microscale Approach, 3rd Ed. – BU custom edition, W.B. Saunders, 2000.
  3. Molecular models (optional, highly suggested): Many suitable styles (e.g., space-filling, ball-and-stick, framework) are available. Recommended: Duluth’s MM-005 set.
  4. Lab coat, notebook and safety goggles (for laboratory sessions).

 

2. Metodologías docentes y tiempo de trabajo del estudiante

2.1. Presencialidad

 

 

2.2. Relación de actividades formativas

LECTURES. Before you come to lecture you are expected to complete a carefully reading of the sections from the text. This allows you to review material you might already know. You will also have an idea about what material is coming. You will know what information is in the book - and you won't have to write it all down in class. You may even be able to generate a few questions. You can pay special attention to any unclear parts during lecture. In-class tests of quizzes about the topic of the lecture can be given by teachers to students in seminar sessions with or without prior notice.

It is also recommended that you do practice questions/problems from the text and lectures. These questions serve to reinforce concepts learned in lecture and from reading the text. They also show how those concepts can be applied to problems. As such, they will help to prepare you for the in-class tests and final exam.

SEMINARS/DISCUSSION SECTIONS. Studying organic chemistry means doing problems. The students will be given a problem set (seminar worksheets) homework assignment and asked to apply the concepts provided in the text and lectures in ways other than the text or lecture do. Organic chemistry involves a problem-solving method that many of you may not have seen before. The unique feature of OC problems is that sometimes the problems can be solved forwards; sometimes they have to be solved backwards! Sometimes there is no single way to solve a problem; often solving Organic Chemistry problems is a challenge! However, while working on the problems, you will learn how to organize a lot of sometimes seemingly disparate pieces of information and figure out which one you need. You do not have to memorize concepts, working on the problems you became familiar with these concepts by using them and understanding their context.  If you can learn to do organic chemistry, you will acquire valuable problem-solving skills.

The assigned problems will serve as the primary focus of the discussion sessions. During the discussion sessions, the instructor and students discuss about problem-solving strategies to improve student capabilities. All students will participate in the scheduled discussion section. Do not look at the answer until you have given the problem a serious try. Work the in-chapter problems pertaining to the assigned sections in the text, do as many end-of-chapter problems needed to gain mastery of the material. Some of the end of the chapter questions will be on your exams.

Recall that there is also mandatory homework due every week.

Attendance is mandatory. Students are expected to arrive on time and to actively participate in all of the lecture and discussion sections. A portion of your course grade will be awarded based on your discussion work, including (on-time) attendance and engagement (in group work and class-wide exercises) in discussion. If you actively and consistently participate in lectures and seminars, if your grade in the class is on a grade border you will be boosted to the higher grade. Working on homework assignments during discussion is not allowed.

HELP OUTSIDE OF CLASS. Please, arrange a meeting and come to office hours. Please keep current with the lecture material: cramming the night before an exam usually fails to produce adequate results because most students cannot effectively absorb the subject matter in a short amount of time.

CONCERNS. If you are experiencing difficulty, please contact your course instructor without delay. If dropping the course appears to be in your best interest, we still would like to work through the decision with you. We are also happy to advise you on appropriate choices for your academic program.

 

LAB ASSIGNMENTS:

1) Prelab Questions. Prelab questions for each lab can be found on LAB MANUAL before the procedure. These questions must be answered before you come to lab.

2) Lab Notebook. A most important skill is the ability to record clearly the phenomena observed in the course of the experiment since these frequently are a sign of important chemical events. Examples of observations to be noted are color changes, the evolution of heat, the liberation of gas, the physical state and appearance of starting materials, intermediate reaction mixtures, and crude and purified products, etc. Set up your lab notebook so that observations can be recorded on the same page as the portion of the experimental procedure which is being observed. Data will be largely quantitative in nature and should be recorded with appropriate units. Examples include melting and boiling point ranges, quantities of materials used and products obtained, percent yields, reaction times, spectroscopic absorption maxima, Rf values, retention times, etc. All information should be recorded in your lab notebook.

3) Post-lab questions. (results/discussion/spectral data).

 

Activity

# hours

Lectures

50

Seminars/practical sessions

20

Laboratory

25

Exams

10

Office hous

5

3. Sistemas de evaluación y porcentaje en la calificación final

3.1. Convocatoria ordinaria

  • MID-TERM EXAMS (MTE): Three 80-minute exams are administered along the course (location to be announced at least two weeks in advance) in additional time to the lecture meeting time. All MTE are cumulative. MTE are graded on a 10-point basis. Your lowest MTE score will be assigned a lower percentage to the final grade. No make-up lecture exams are given for any reason (only in exceptional circumstances); please do not ask to take a make-up lecture exam nor ask to take a lecture exam at other than the scheduled date and time. Do not make travel plans that conflict with the lecture exams.
  • IN-CLASS TESTS OF QUIZZES. Four 15-20 minute in-class tests with a problem about the topic of the lecture will be given by teachers to students in some seminar sessions along the course. All in-class tests are cumulative and graded on a 10-point basis. Your lowest in-class test score will be dropped in calculating your course grade.
  • FINAL EXAM (FE): A cumulative 2.5-3-hour final exam will be administered at the end of the course (exact time and location to be announced at least two weeks in advance). FE is graded on a 10-point basis.

There are no make-up exams whatsoever. Incomplete grades are not accepted in this abroad program, as you will be leaving the site at the end of the semester.

3.1.1. Relación actividades de evaluación

  

 

Evaluable activity

Percentage

MTE

15%

MTE

15%

MTE (lowest score)

7.5%

FE

40%

IN-CLASS TESTS

7.5%

LABORATORY

15%

 

Course grades are calculated by the following formula:

CH203 Grade = MTE · 0.15 + MTE · 0.15 + MTE · 0.075 (lowest score)+ FE · 0.4 + In-class test · 0.075 + Lab ·0.15

where MTE1 andMTE2 are the scores of your two highest of three MID-TERM-EXAMS, FE is the score of your FINAL EXAM, SEMINARS is the score of seminars and discussion sessions, and LABORATORY is your lab score. All individual scores are based on 10 points. The maximum score is 10. The minimum score to pass is 5.0.

Spanish grade ranges are:

  • Lowest (no pass): 0-4,9: Suspenso (SS).
  • Fair (pass): 5,0-6,9: Aprobado (AP).
  • Intermediate-High: 7,0-8,9: Notable (NT).
  • Highest: 9,0-10: Sobresaliente (SB).

There are no extra-credit projects to offset poor performance on exams/seminars. Please do not ask to have the course grade you earn raised gratuitously because you fail to satisfy the GPA requirements of your program of study, scholarship, etc.

3.2. Convocatoria extraordinaria

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3.2.1. Relación actividades de evaluación

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4. Cronograma orientativo

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