1fall, 2009 chem305 organic chemistry i introduction dr. ralph c. gatrone department of chemistry...

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1 Fall, 2009 Fall, 2009 CHEM305 CHEM305 Organic Chemistry I Organic Chemistry I Introduction Introduction Dr. Ralph C. Gatrone Dr. Ralph C. Gatrone Department of Chemistry and Department of Chemistry and Physics Physics Virginia State University Virginia State University Fall, 2009 Fall, 2009

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11Fall, 2009Fall, 2009

CHEM305 CHEM305 Organic Chemistry IOrganic Chemistry I

IntroductionIntroduction

Dr. Ralph C. GatroneDr. Ralph C. GatroneDepartment of Chemistry and PhysicsDepartment of Chemistry and Physics

Virginia State UniversityVirginia State UniversityFall, 2009Fall, 2009

Fall, 2009Fall, 2009 22

ObjectivesObjectives

• Discuss syllabusDiscuss syllabus

• Discuss course requirementsDiscuss course requirements

• Review general chemistryReview general chemistry

Fall, 2009Fall, 2009 33

Organic Chemistry IOrganic Chemistry ICHEM305-01-081CHEM305-01-081

• Office HoursOffice Hours– T: 2:00 – 5:00 and W: 9:00 – 12:00T: 2:00 – 5:00 and W: 9:00 – 12:00– by appointment (524-5762)by appointment (524-5762)

• Office: HM239NbOffice: HM239Nb

• Email: Email: [email protected]

• I only respond to an email address I only respond to an email address that ends in @vsu.eduthat ends in @vsu.edu

Fall, 2009Fall, 2009 44

Organic Chemistry 1Organic Chemistry 1Course DescriptionCourse Description

• Survey of compounds composed of carbonSurvey of compounds composed of carbon

• NomenclatureNomenclature

• StructureStructure

• Physical propertiesPhysical properties

• ReactionsReactions

• MechanismsMechanisms

Fall, 2009Fall, 2009 55

Course EmphasisCourse Emphasis

• Organic reactionsOrganic reactions

• Molecular orbital theoryMolecular orbital theory

• Organic MechanismsOrganic Mechanisms

• Molecules of biological importanceMolecules of biological importance

• Critical thinking skillsCritical thinking skills

• Skills necessary to do well onSkills necessary to do well on

• MCAT, PCAT, OAT, DAT, othersMCAT, PCAT, OAT, DAT, others

Fall, 2009Fall, 2009 66

RolesRoles

• My roleMy role

• ProfessorProfessor

• GuideGuide

• Your RoleYour Role

• StudentStudent

• Understand the material!Understand the material!

Fall, 2009Fall, 2009 77

The Teacher versus the The Teacher versus the Professor Professor

• A A teacherteacher conveys information to provide a conveys information to provide a student with certain skills and a knowledge student with certain skills and a knowledge base.base.

• A A professorprofessor professes the truth about their professes the truth about their area of expertise while providing the student area of expertise while providing the student with the skills to accept or refute that truth.with the skills to accept or refute that truth.

• Ideally the professor imparts a sense of Ideally the professor imparts a sense of wonder such that the student will push the wonder such that the student will push the limits of our understanding.limits of our understanding.

• The The studentstudent develops the necessary skills develops the necessary skills and knowledge base to succeed.and knowledge base to succeed.

Fall, 2009Fall, 2009 88

Requirements and Requirements and PrerequisitesPrerequisites• Course MaterialsCourse Materials• Text: Text: Organic Chemistry A Biological ApproachOrganic Chemistry A Biological Approach, John McMurry, John McMurry• You must purchase the book.You must purchase the book.• A study guide is available. It is not required.A study guide is available. It is not required.

• PrerequisitesPrerequisites• CHEM101 or 111, 102 or 112CHEM101 or 111, 102 or 112• Associated LaboratoriesAssociated Laboratories

• Foundation from General ChemistryFoundation from General Chemistry• Quantum mechanicsQuantum mechanics• Solution chemistrySolution chemistry• Acid Base ChemistryAcid Base Chemistry• KineticsKinetics• ThermodynamicsThermodynamics

Fall, 2009Fall, 2009 99

Prerequisites are criticalPrerequisites are critical

• You must have passed these coursesYou must have passed these courses

• If you have not passed these coursesIf you have not passed these courses

• You must drop the course You must drop the course immediatelyimmediately

• If not sooner!If not sooner!

Fall, 2009Fall, 2009 1010

HomeworkHomework

• EveryEvery problem in the Text is recommended. problem in the Text is recommended.

• However,However,– They will not be graded.They will not be graded.– They will not be collected.They will not be collected.– They will not be discussed in class.They will not be discussed in class.– They are available to you to determine if you They are available to you to determine if you

understand the material.understand the material.– If you choose not to do the problems it is nearly If you choose not to do the problems it is nearly

a guarantee that you will not pass this class.a guarantee that you will not pass this class.

Fall, 2009Fall, 2009 1111

EvaluationEvaluation

• Test 1: Chapters 1 – 6 Test 1: Chapters 1 – 6 100pts100pts• Test 2: Chapters 1 – 7 Test 2: Chapters 1 – 7 100pts100pts• Test 3: Chapters 1 – 10 Test 3: Chapters 1 – 10 100 pts100 pts• Final Exam Chapters 1 – 10Final Exam Chapters 1 – 10 200pts200pts

• Total Possible Total Possible 500pts500pts

Fall, 2009Fall, 2009 1212

Evaluation – Grade Evaluation – Grade CalculationCalculation

• Final Grades will be computed:Final Grades will be computed:– Earned PointsEarned Points Final GradeFinal Grade

>450>450 AA

400 – 449400 – 449 BB

325 – 399325 – 399 CC

250 – 324250 – 324 DD

<249<249 FF

Fall, 2009Fall, 2009 1313

Extra CreditExtra Credit

• No extra credit will be given. No extra credit will be given.

• If you follow my instructionsIf you follow my instructions

• You will not need it. You will not need it.

• If you do not follow these instructionsIf you do not follow these instructions

• It will not help.It will not help.

Fall, 2009Fall, 2009 1414

Special ConsiderationSpecial Consideration

• Grades are earned. Grades are earned. • Grades are not awardedGrades are not awarded• Grades cannot be negotiated. Grades cannot be negotiated. • Grades cannot be influenced by factors such as:Grades cannot be influenced by factors such as:• I like youI like you• You like me (rare circumstance)You like me (rare circumstance)• I feel sorry for youI feel sorry for you• You are a nice person in good standing with the university.You are a nice person in good standing with the university.• You will lose a scholarshipYou will lose a scholarship• You will forfeit some tuition reimbursementYou will forfeit some tuition reimbursement• A previously excellent GPA will be ruinedA previously excellent GPA will be ruined• You will be sent back to a repressive countryYou will be sent back to a repressive country• You will not graduate on time!You will not graduate on time!

Fall, 2009Fall, 2009 1515

AttendanceAttendance

• Assumption: you are adult studentsAssumption: you are adult students• Attendance in lecture is expectedAttendance in lecture is expected• Do not ask me to re-lecture material you Do not ask me to re-lecture material you

missed.missed.• Regardless of your excuse for missing class Regardless of your excuse for missing class

you made a choice not to attend and you are you made a choice not to attend and you are responsible for the material you missed.responsible for the material you missed.

• Attendance at examinations is required.Attendance at examinations is required.• A missed examination will receive a zero.A missed examination will receive a zero.• No excuse will be accepted.No excuse will be accepted.• A missed final exam will receive a zero.A missed final exam will receive a zero.

Fall, 2009Fall, 2009 1616

A Word on ExaminationsA Word on Examinations

• Examinations will consist of several short Examinations will consist of several short answer questions.answer questions.

• The final examination will contain 100 The final examination will contain 100 multiple choice questions. multiple choice questions.

• These will be similar to the questions These will be similar to the questions encountered on the MCAT, DAT, PCAT, etc.encountered on the MCAT, DAT, PCAT, etc.

Fall, 2009Fall, 2009 1717

A Word on the Final ExamA Word on the Final Exam

• The final exam is scheduled by the The final exam is scheduled by the university.university.

• This schedule minimizes conflicts between This schedule minimizes conflicts between rooms and courses.rooms and courses.

• If the scheduled date and time happens to If the scheduled date and time happens to be inconvenient for you, please withdraw be inconvenient for you, please withdraw from the course today.from the course today.

• There is no excuse that I will accept that There is no excuse that I will accept that would permit you take the exam early.would permit you take the exam early.

Fall, 2009Fall, 2009 1818

Communication in Class Communication in Class

• Turn your cell phone off.Turn your cell phone off.• Turn your desire to communicate with Turn your desire to communicate with

anyone but me off.anyone but me off.• An offending cell phone (includes text An offending cell phone (includes text

messaging) will result in the cancelation of messaging) will result in the cancelation of that day’s lecture.that day’s lecture.

• If a class is cancelled because of an If a class is cancelled because of an offensive cell phone the class will be held offensive cell phone the class will be held responsible for the material not covered responsible for the material not covered me by in that class.me by in that class.

Fall, 2009Fall, 2009 1919

Expectations - StudentsExpectations - Students

• A professional student is expected toA professional student is expected to

• attend classattend class

• purchase course materialspurchase course materials

• studystudy

• do the homeworkdo the homework

• be prepared for classbe prepared for class

• be prepared for testsbe prepared for tests

• do welldo well

Fall, 2009Fall, 2009 2020

Expectations - Faculty Expectations - Faculty

• I am expected toI am expected to

• attend classattend class

• prepare lecture materialsprepare lecture materials

• present lecture materialspresent lecture materials

• prepare and grade testsprepare and grade tests

• be available for outside consultationbe available for outside consultation

• keep accurate recordskeep accurate records

Fall, 2009Fall, 2009 2121

Important NoteImportant Note

• I am not expected toI am not expected to

• Provide extra creditProvide extra credit

• Negotiate gradesNegotiate grades

Fall, 2009Fall, 2009 2222

Doing WellDoing Well

• Read the chapter before lectureRead the chapter before lecture• Attend lectureAttend lecture• Take notesTake notes• Do not rely on copies of Power PointsDo not rely on copies of Power Points• Re-read the chapter after lectureRe-read the chapter after lecture• Review lecture notes dailyReview lecture notes daily• Rewriting the lecture notes is strongly suggestedRewriting the lecture notes is strongly suggested• Keep, maintain, and study note cardsKeep, maintain, and study note cards• Do homework problems.Do homework problems.• Form a study groupForm a study group• Learn the functional groupsLearn the functional groups

Fall, 2009Fall, 2009 2323

The Functional GroupsThe Functional Groups

• Families of Organic CompoundsFamilies of Organic Compounds• Millions of compounds Millions of compounds • Thousands discovered every yearThousands discovered every year• Task of knowing the chemistry would be overwhelmingTask of knowing the chemistry would be overwhelming• However, compounds can be grouped into families However, compounds can be grouped into families • Based upon common structural features Based upon common structural features • Suggests common reactivitySuggests common reactivity• You must know the Table of Functional Groups provide You must know the Table of Functional Groups provide

by me. Others will come along during the semesterby me. Others will come along during the semester• This course is a survey the chemistry and properties of This course is a survey the chemistry and properties of

organic compoundsorganic compounds• It is taught as a tour of the functional groupsIt is taught as a tour of the functional groups

Fall, 2009Fall, 2009 2424

Functional GroupsFunctional GroupsR CH3

alkane

R X

alkyl

halide

(X = F, Cl, Br, I

R

CH2

alkene

RR

alkyne

arene

R O R

ether

R OH

alcohol

R S R

sulfide

R SH

thiol

OH

phenol

R S R

O

sulfoxidesulfone

R S R

O

O

sulfonic acid

R S OH

O

O

Fall, 2009Fall, 2009 2525

Functional GroupsFunctional Groups

R H

O

aldehyde

R R

O

ketone

R OH

O

carboxylic acid

R Cl

O

carboxylic acid chloride

R O

O O

R

carboxylic acid anhydride

R O

O

R

ester

R

O

NH2

amide

NCH3

nitrile

Fall, 2009Fall, 2009 2626

Wow!Wow!

• That’s a lot of stuff to learn and you That’s a lot of stuff to learn and you expect me to know it.expect me to know it.

• Do you believe that this is the only Do you believe that this is the only course I am taking?course I am taking?

• This is an important question which This is an important question which we must answer!we must answer!

• You may not like the answerYou may not like the answer..

Fall, 2009Fall, 2009 2727

Is this the only course I am Is this the only course I am taking?taking?

• YESYES• Time invested = Desired gradeTime invested = Desired grade• Average professional – 60 hours/weekAverage professional – 60 hours/week• Professional studentProfessional student• ~18 hours/week in class~18 hours/week in class• 60 – 18 = 4260 – 18 = 42• 42hours/6 days = 7 hours per day42hours/6 days = 7 hours per day• Or approximately 2 hours/classOr approximately 2 hours/class• Time invested = Desired gradeTime invested = Desired grade

Fall, 2009Fall, 2009 2828

Why?Why?

• Your Role: Your Role: • The job of understanding the material is yours.The job of understanding the material is yours.

• My Role: My Role: • GuideGuide• I’ve been here.I’ve been here.• I’ve done it.I’ve done it.• I have the t-shirt (at least a C and a B in Organic I and II)I have the t-shirt (at least a C and a B in Organic I and II)

• Best advice I can give you!Best advice I can give you!

• If you choose to study organic chemistry like other courses If you choose to study organic chemistry like other courses you have taken you might do well, but the odds are against it.you have taken you might do well, but the odds are against it.

Fall, 2009Fall, 2009 2929

Major ComplaintMajor Complaint

• I can’t possibly learn this stuff.I can’t possibly learn this stuff.• I can’t learn all of those functional I can’t learn all of those functional

groups.groups.• Why? Again you aren’t going to like the Why? Again you aren’t going to like the

answer.answer.• You don’t study enough.You don’t study enough.• Average of 42 hours per week beyond Average of 42 hours per week beyond

your class is expectedyour class is expected• To obtain a C - the average gradeTo obtain a C - the average grade

CommentComment

• I have never met a student who I have never met a student who could not learn organic chemistry.could not learn organic chemistry.

• Some students might make 3 or Some students might make 3 or more attempts to learn the material.more attempts to learn the material.

• The number of attempts required is The number of attempts required is dependent upon you.dependent upon you.

Fall, 2009Fall, 2009 3030

Why don’t students learn?Why don’t students learn?

• FearFear• Wrong attributesWrong attributes• Lack of confidenceLack of confidence• Too much confidenceToo much confidence• Failure to follow throughFailure to follow through• Paralysis due to personal/family problemsParalysis due to personal/family problems• Failure to imitate best practicesFailure to imitate best practices• Lack of balance of social and academic Lack of balance of social and academic

lifelife• Failure to appreciate delayed gratification.Failure to appreciate delayed gratification.

Fall, 2009Fall, 2009 3131

Guide’s RoleGuide’s Role

Fall, 2009Fall, 2009 3232

YouYour Goals

Study SessionsStudy Sessions

• Study sessions will be heldStudy sessions will be held

• Tuesday and ThursdayTuesday and Thursday

• 7 – 8 AM7 – 8 AM

• They are not mandatoryThey are not mandatory

• The first one will be held next Tuesday.The first one will be held next Tuesday.

• The last one the first time I enter the The last one the first time I enter the room and no one is here.room and no one is here.

Fall, 2009Fall, 2009 3333

Important Goals of Important Goals of Organic ChemistryOrganic Chemistry

• Prepare you for MCAT, DAT, OAT, etc.Prepare you for MCAT, DAT, OAT, etc.

• Assist in your transition from a Assist in your transition from a student to a scholar.student to a scholar.

• This is done byThis is done by– Mastery of contentMastery of content– Application of theoretical constructsApplication of theoretical constructs– Developing skills to critique, analyze, Developing skills to critique, analyze,

research, discuss, write, and present.research, discuss, write, and present.

Fall, 2009Fall, 2009 3434

Fall, 2009Fall, 2009 3535

What is the minimum I need to What is the minimum I need to do to get out of here?do to get out of here?• Depends, what grade do you want?Depends, what grade do you want?• W, F, or DW, F, or D

– Attend class irregularlyAttend class irregularly– Study just before each testStudy just before each test– Rely upon your memoryRely upon your memory

• C, B, or AC, B, or A– Never miss classNever miss class– Read the chapter before and after classRead the chapter before and after class– Review lecture notes dailyReview lecture notes daily– Study 2 hours per day, 6 days per weekStudy 2 hours per day, 6 days per week– Make and use note cardsMake and use note cards– Do all assigned homework problemsDo all assigned homework problems– See me for assistance early and oftenSee me for assistance early and often

Fall, 2009Fall, 2009 3636

Why Study Organic Why Study Organic Chemistry?Chemistry?• Required for MajorRequired for Major• I will never need it.I will never need it.• Required for Major Required for Major • I might need it someday.I might need it someday.• ElectiveElective• I will certainly never need it.I will certainly never need it.• Best course on campus.Best course on campus.• Best instructor on campusBest instructor on campus• Only class available at this forsaken timeOnly class available at this forsaken time• Need to lower my GPA.Need to lower my GPA.

Who studies Organic Who studies Organic Chemistry?Chemistry?• ChemistryChemistry• BiologyBiology• Pre-medicinePre-medicine• Pre-dentistryPre-dentistry• Pre-pharmacyPre-pharmacy• Animal ScienceAnimal Science• Pre-veterinarianPre-veterinarian• NutritionNutrition• Other programs not offered at VSU also Other programs not offered at VSU also

require organic chemistry.require organic chemistry.

Fall, 2009Fall, 2009 3737

A Common ThreadA Common Thread

• SciencesSciences

• Scientists do scienceScientists do science

• Scientists do NOT do sloppy workScientists do NOT do sloppy work

• Sloppy scientists fulfill Darwin’s Sloppy scientists fulfill Darwin’s principles!principles!

Fall, 2009Fall, 2009 3838

Fall, 2009Fall, 2009 3939

Some More Important Some More Important QuestionsQuestions• Is drop/add over?Is drop/add over?• Are there any other instructors available?Are there any other instructors available?• When is the last day to withdraw?When is the last day to withdraw?• What is the minimum I need to pass?What is the minimum I need to pass?• What is organic chemistry?What is organic chemistry?• Before we start, let’s review some general Before we start, let’s review some general

chemistry concepts that are important for chemistry concepts that are important for us because organic chemistry depends us because organic chemistry depends upon a fundamental understanding of upon a fundamental understanding of general chemistrygeneral chemistry

Fall, 2009Fall, 2009 4040

Important NoteImportant Note

• If you decide to withdraw from the If you decide to withdraw from the lecturelecture

• at any point in the semester,at any point in the semester,

• You must withdraw from the You must withdraw from the laboratory!laboratory!

• Let’s review General Chemistry!Let’s review General Chemistry!

Fall, 2009Fall, 2009 4141

Review of General Review of General ChemistryChemistry• To be here you met the pre-requisites.To be here you met the pre-requisites.• You have taken General Chemistry I and II.You have taken General Chemistry I and II.• You have learned the followingYou have learned the following• The Periodic TableThe Periodic Table• Structure of the atom and electron configurationStructure of the atom and electron configuration• Lewis dot structures and bondingLewis dot structures and bonding• Basic chemical nomenclatureBasic chemical nomenclature• StoichiometryStoichiometry• Energy and chemical reactionsEnergy and chemical reactions• Chemical equilibrium, acids, basesChemical equilibrium, acids, bases• Thermodynamics and basic kineticsThermodynamics and basic kinetics• Assumption for Organic Chemistry IAssumption for Organic Chemistry I• You received an A in General Chemistry I and II.You received an A in General Chemistry I and II.

Fall, 2009Fall, 2009 4242

Review of General Review of General ChemistryChemistry• NucleusNucleus• OrbitalsOrbitals• Electronic ConfigurationElectronic Configuration• Chemical BondingChemical Bonding• Ionic and CovalentIonic and Covalent• Hybridization of Carbon’s OrbitalsHybridization of Carbon’s Orbitals• spsp33, sp, sp22, and sp hybridization, and sp hybridization• Molecular Orbital TheoryMolecular Orbital Theory• Formation of C-C sigma and pi bondsFormation of C-C sigma and pi bonds

Fall, 2009Fall, 2009 4343

Review of General Review of General ChemistryChemistry• ElectronegativityElectronegativity

• F is the most electronegative atomF is the most electronegative atom

• Electronegativity decreases down groupElectronegativity decreases down group

• Electronegativity decreases right to leftElectronegativity decreases right to left

• Polar covalent bondingPolar covalent bonding

• Dipole momentsDipole moments

• Formal ChargeFormal Charge

Fall, 2009Fall, 2009 4444

Review of General Review of General ChemistryChemistry

• Review ResonanceReview Resonance

• Consider two structuresConsider two structures

• Acetate ion and BenzeneAcetate ion and Benzene

Fall, 2009Fall, 2009 4545

Acetate IonAcetate Ion

• Two line structures are possibleTwo line structures are possible• C=O and C-O bondsC=O and C-O bonds• However, both C-O bonds are 127pmHowever, both C-O bonds are 127pm• C=O is 120pm and C-O is 135pmC=O is 120pm and C-O is 135pm

O

O

O

O

Fall, 2009Fall, 2009 4646

BenzeneBenzene

• Two possible line structuresTwo possible line structures• Neither is correctNeither is correct

• C-C bonds in benzene are all 139pmC-C bonds in benzene are all 139pm• C-C bond is 154pm and C=C is 134pmC-C bond is 154pm and C=C is 134pm

• Problem encounteredProblem encountered• Drawing these moleculesDrawing these molecules• True structure can’t be drawnTrue structure can’t be drawn

Fall, 2009Fall, 2009 4747

Drawing these StructuresDrawing these Structures

• We cannot draw the true structureWe cannot draw the true structure

• Therefore, we invoke idea – Therefore, we invoke idea –

• resonanceresonance

• Individual structures are resonance Individual structures are resonance hybrids of true structurehybrids of true structure

• We cannot draw the true structureWe cannot draw the true structure

Fall, 2009Fall, 2009 4848

Resonance StructuresResonance Structures

O

O

O

O

Resonance Hybrids

Fall, 2009Fall, 2009 4949

Resonance GuidelinesResonance Guidelines

• Individual resonance forms are not realIndividual resonance forms are not real• Resonance forms differ only in Resonance forms differ only in

placement of electrons (pi or non-placement of electrons (pi or non-bonding)bonding)

• Resonance forms do not have to be Resonance forms do not have to be equivalentequivalent

• Resonance forms obey valence rulesResonance forms obey valence rules• Hybrid is more stable than resonance Hybrid is more stable than resonance

formsforms

Fall, 2009Fall, 2009 5050

Review of Acids and BasesReview of Acids and Bases

• Two Definitions of Acids and BasesTwo Definitions of Acids and Bases

• Bronsted-LowryBronsted-Lowry

• LewisLewis

Fall, 2009Fall, 2009 5151

Bronsted – LowryBronsted – Lowry

• Acid donates a protonAcid donates a proton

• Base accepts a protonBase accepts a proton

• Consider following reaction:Consider following reaction:

HA + HOH H3O+ + A-

Keq =

[H3O+] [A-]

[HA] [HOH]

Fall, 2009Fall, 2009 5252

In dilute solutionIn dilute solution

• [HOH] = 55.5M, nearly constant[HOH] = 55.5M, nearly constant

• Therefore, define the acidity constantTherefore, define the acidity constant

HA + HOH H3O+ + A-

Keq =

[H3O+] [A-]

[HA] [HOH]

Keq =

[H3O+] [A-]

[HA] [HOH]Ka =

Fall, 2009Fall, 2009 5353

Acid StrengthAcid StrengthHA + HOH H3O

+ + A-

Strong acids – equilibrium is to the rightStrong acids – equilibrium is to the right

KKaa is large is large

Weak acids – equilibrium is to the leftWeak acids – equilibrium is to the left

Ka is smallKa is small

Range of values is 10Range of values is 101515 (strongest) to 10 (strongest) to 10-60-60 (weakest)(weakest)

Fall, 2009Fall, 2009 5454

pKa ValuespKa Values

• pKa = -logKapKa = -logKa

• Values range -7 (strongest) to 60 (weakest)Values range -7 (strongest) to 60 (weakest)

• As strength of acid increasesAs strength of acid increases

• Strength of base decreasesStrength of base decreases

• HCl pka = -7 (a strong acid)HCl pka = -7 (a strong acid)

• Conjugate base: ClConjugate base: Cl-- is very weak is very weak

• H-CHH-CH33 pKa = 60 (a weak acid)

• Conjugate base CH3- is very strong

Fall, 2009Fall, 2009 5555

A Few pKa ValuesA Few pKa Values(learn this list as we will add to (learn this list as we will add to

it)it)• EtOHEtOH 1616

• HOHHOH 15.715.7

• HCNHCN 9.39.3

• HOAcHOAc 4.84.8

• Phosphoric AcidPhosphoric Acid 2.22.2

• Nitric AcidNitric Acid -1.3-1.3

• HClHCl -7-7

Fall, 2009Fall, 2009 5656

pKa ValuespKa Values

• Learn values given in Table 2.3 (p 52)Learn values given in Table 2.3 (p 52)

• Use these values to predict acid base reactionsUse these values to predict acid base reactions

• Consider the following:Consider the following:

HOAc + NaOH NaOAc + HOH

Which is the stronger acid?

pKa of HOAc = 4.76

pKa of HOH = 15.7 (conjugate acid of NaOH)

HOAc = stronger acid than HOH, HO- = stronger base than AcO-

Reaction proceeds to the right.

Fall, 2009Fall, 2009 5757

Lewis Acids and BasesLewis Acids and Bases

• Lewis Acids – accept an electron pairLewis Acids – accept an electron pair

• Lewis Bases – donate an electron Lewis Bases – donate an electron pairpair

• The electron pair ends up shared by The electron pair ends up shared by the acid-base as a covalent bondthe acid-base as a covalent bond

Fall, 2009Fall, 2009 5858

Lewis Acids Lewis Acids

• The Lewis definition of acidity includes metal cations The Lewis definition of acidity includes metal cations • such as Mgsuch as Mg22+ +

• Neutral Group 3A compoundsNeutral Group 3A compounds• such as BFsuch as BF33 and AlCl and AlCl33

• Neutral transition-metal compoundsNeutral transition-metal compounds• such as TiClsuch as TiCl44, FeCl, FeCl33, ZnCl, ZnCl22, and SnCl, and SnCl44

• The combination of a Lewis acid and a Lewis base can The combination of a Lewis acid and a Lewis base can shown with a curved arrow from base to acidshown with a curved arrow from base to acid

Fall, 2009Fall, 2009 5959

Lewis BasesLewis Bases

• Donate an electron pairDonate an electron pair

• Molecules must contain an electron Molecules must contain an electron pairpair

Fall, 2009Fall, 2009 6060

Lewis Acids and BasesLewis Acids and Bases

• HH++ is a Lewis acid is a Lewis acid

• Accepts electron pair from waterAccepts electron pair from water

• Hydronium ion (HHydronium ion (H33OO++))

• Water is a Lewis baseWater is a Lewis base

• Donates electron pair to the protonDonates electron pair to the proton

Fall, 2009Fall, 2009 6161

Illustration of Curved Arrows in Illustration of Curved Arrows in Following Lewis Acid-Base ReactionsFollowing Lewis Acid-Base Reactions

Fall, 2009Fall, 2009 6262

Review of General Review of General ChemistryChemistry• Our review of general chemistry is done.Our review of general chemistry is done.

• We have also covered Chapters 1 and 2 We have also covered Chapters 1 and 2 inin

• Organic Chemistry: A Biological Organic Chemistry: A Biological Approach Approach by John McMurryby John McMurry

• Now, we can askNow, we can ask

• What is organic chemistry?What is organic chemistry?

• Why am I studying this course?Why am I studying this course?

Fall, 2009Fall, 2009 6363

Organic ChemistryOrganic Chemistry

• is the study of the chemistry of compounds is the study of the chemistry of compounds that contain carbon.that contain carbon.

• Carbon is a unique element in the Periodic Carbon is a unique element in the Periodic Table in that Table in that

• (1) it likes to bond to itself and(1) it likes to bond to itself and

• (2) The number of carbon atoms that can be (2) The number of carbon atoms that can be bonded in a chain appear to be limitless.bonded in a chain appear to be limitless.

Fall, 2009Fall, 2009 6464

Organic Chemistry and Organic Chemistry and BiologyBiology• Biological revolutionBiological revolution• Biotechnological advances Biotechnological advances

– Unprecedented scaleUnprecedented scale– Foundation is organic chemistryFoundation is organic chemistry

• All organic molecules contain CarbonAll organic molecules contain Carbon• 99% of 26 million molecules contain C99% of 26 million molecules contain C• Possible because of Carbon’s Possible because of Carbon’s

electronic structureelectronic structure

Fall, 2009Fall, 2009 6565

Questions to consider in Questions to consider in CHEM305CHEM305

• Why do organic molecules have certain Why do organic molecules have certain properties? properties?

• Why do certain reactions occur?Why do certain reactions occur?• Why do other reactions not occur?Why do other reactions not occur?• What drives these processes?What drives these processes?

• Can we predict the presence or absence of Can we predict the presence or absence of certain properties?certain properties?

• Can we make new materials with other Can we make new materials with other desired properties?desired properties?

Fall, 2009Fall, 2009 6666

Biological Organic Biological Organic ChemistryChemistry• Know what and why something happenedKnow what and why something happened• Molecular levelMolecular level• Understanding is based on foundationUnderstanding is based on foundation• BondingBonding• Bond polarityBond polarity• Acid base behaviorAcid base behavior• Hydrogen bondingHydrogen bonding• Organic chemistry depends upon a Organic chemistry depends upon a

fundamental understanding of general fundamental understanding of general chemistrychemistry