CHEM 341: Organic Chemistry I

Size: px
Start display at page:

Download "CHEM 341: Organic Chemistry I"

Transcription

1 EM 341: rganic hemistry I at North Dakota tate University Final Exam - tudy Guide Reactions to know ubstitution of Alcohols R X R X N 1 ubstitution - N 2 ubstitution 3 carbocation best 2 carbocation ok - 1 will not form carbocation R 2 R 2 N 2 ubstitution - will work with 1 and 2 alcohols, not 3 alcohols R P 3 R 3 P 3 P P hem 341 Final Exam tudy Guide! page 1! spring 2012

2 Free Radical alogenation light or heat Initiation Propogation Termination Elimination of Alcohols R 2 R 2 R 2 R 2 E1 Elimination - proceeds through carbocation, 2 and 3 alcohols 3 P 4-2 E2 Elimination - 1 alcohols, requires anti-periplanar arrangement 3 P 4 2 P 4 2 P 4 hem 341 Final Exam tudy Guide! page 2! spring 2012

3 Elimination of alides X R 2 R 2 R R 2 R 2 R E2 Elimination - 1, 2 or 3 halides with strong base requires anti-periplanar arrangement K - 3 K 3 E1 elimination can occur under neutral conditions only with 3 halides Electrophilic Addition to Alkenes A B - or A A B A overall equivalent A B - notes 2 ( cat) - Markovnikov reagents B 3 - syn addn, anti-markovnikov then 2 2 / - X X - Markovnikov X 2 X X - bridged, anti addn X 2 / 2 X - bridged, anti addn, Markovnikov 3 P Most stable intermediate Lower energy pathway Markovnikov Addition hem 341 Final Exam tudy Guide! page 3! spring 2012

4 Most stable intermediate Lower energy pathway Markovnikov Addition - A bromonium omide can only come from the bottom and kick off the bromine on the top. This reaction forms the trans product selectively Markovnikov Addition even if there is no full carbocation ydroboration and ydrogenation 1) B 3 2) 2 2 / Na B 2 2 Pd/ anti-markovnikov hydration syn addition syn addition of 2 hem 341 Final Exam tudy Guide! page 4! spring 2012

5 Reduction (ydrogenation) Reactions 2 Pd/ 2 Pd/ 2 Lindlar's atalyst stops at alkene Lindlar's atalyst Pd(Ac) 2 quinoline on a 3 Li N 3 Electrophilic Addition Reactions trans alkene cat. g Ketone 1 equiv 1 equiv 2 1 equiv 2 1 equiv xidation Reactions 3 then Zn/Ac 3 then Zn/ mpba epoxidation hem 341 Final Exam tudy Guide! page 5! spring 2012

6 ubstitution Reactions NaN 2 Na δ δ- 3 3 P P Tos- pyridine Tos Tos- Elimination Reactions or K or NaN 2 K or NaN 2 can be prepared by 2 addition to an alkene a vinyl bromide You should know the mechanistic details of N1, N2, E1 and E2 mechanisms and what factors influence substitution vs elimination pathways. There are a number of different nucleophiles and electrophiles that participate. You should be familiar with those and be able to recognize what various reactants do. hem 341 Final Exam tudy Guide! page 6! spring 2012

7 N 1 N 2 UBTRATE 3 >> 2 > 1 1 > 2 >> 3 NULEPILE Weak K trong LEAVING GRUP table Anions table Anions TEREEM Racemic 100% inversion LVENT Polar Protic Polar Aprotic R-X N 1 E1 N 2 E2 1 X X favored favored with strong base 2 ok ok favored with strong nucleophile favored with strong base 3 favored in protic solvents no base can compete witn N 1 X favored with strong or weak base Good Nucleophiles trong Bases I N R N 3 R R N 2 bulkier is less nucleophilic hem 341 Final Exam tudy Guide! page 7! spring 2012

8 Preparation of onjugated Dienes NB peroxides Kt-Bu t-bu Note that the allylic position is especially easy to form free radicals. alides can be eliminated under base conditions to form conjugated dienes. Alcohols can be eliminated under acidic conditions. Reactions of onjugated Dienes not formed 1,2-addition 1,4-addition Kinetic ontrol 0 71% 29% Thermodynamic ontrol 40 15% 85% Diels-Alder Reactions diene dieneophile cyclic transition state dieneophile 3 exo product minor opposite sides 3 endo product major same side exo transition state 3 3 endo transition state 3 3 opposite sides 3 secondary orbital interaction with the carbonyl pi-bond lowers the energy for this transition state same side 3 hem 341 Final Exam tudy Guide! page 8! spring 2012

9 Electrophilic Aromatic ubstitution 2 Fe 3 NEED T KNW MEANIM NT formed - 2 Fe 3 2 Fe 3 I 2 ui 2 I 2 Fe 3 Fe 4 electrophile 2 Fe 3 Fe 4 electrophile I 2 ui 2 I ui 3 electrophile N N 2 N 2 4 N electrophile Fuming electrophile R- Al 3 R Al 3 88% hem 341 Final Exam tudy Guide! page 9! spring 2012

10 Activating Electron Donating Groups ortho, para directors R strongest (resonance) NR 2 R alkyl weakest (inductive) Deactivating Electron Withdrawing Groups N 2 3 R N meta directors strongest (resonance) X weak ortho, para directors but deactivating ther Reactions of Benzene and ubstituents 3 KMn 4 KMn 4 KMn 4 KMn 4 No Reaction N NB Ph Ph 2 Zn(g) Pd/ 3 2 R Na / N 3 R Pt 2000 psi hem 341 Final Exam tudy Guide! page 10! spring 2012

Double Bonds. Hydration Rxns. Hydrogenation Rxns. Halogenation. Formation of epoxides. Syn addition of 2 OH. Ozonolysis

Double Bonds. Hydration Rxns. Hydrogenation Rxns. Halogenation. Formation of epoxides. Syn addition of 2 OH. Ozonolysis Double Bonds What do we do with double bonds? We do addition reactions. In an addition reaction, something is added to both carbons involved in a double bond (or not involved in the double bond, in the

More information

Chapter 10 Conjugation in Alkadienes and Allylic Systems

Chapter 10 Conjugation in Alkadienes and Allylic Systems . 0 onjugated Systems hapter 0 onjugation in Alkadienes and Allylic Systems onjugated systems are those in which a π-bond is connected or conjugated (from the Latin conjugare which means to link r yoke

More information

Electrophilic Addition Reactions

Electrophilic Addition Reactions Electrophilic Addition Reactions Electrophilic addition reactions are an important class of reactions that allow the interconversion of C=C and C C into a range of important functional groups. Conceptually,

More information

4/18/2011. 9.8 Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions

4/18/2011. 9.8 Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions 9.8 Substituent effects in the electrophilic substitution of an aromatic ring Substituents affect the reactivity of the aromatic ring Some substituents activate the ring, making it more reactive than benzene

More information

CHEM 211 CHAPTER 16 - Homework

CHEM 211 CHAPTER 16 - Homework CHEM 211 CHAPTER 16 - Homework SHORT ANSWER Consider the Friedel-Crafts alkylation reaction below to answer the following question(s): 1. Refer to the reaction above. Draw the structure of the electrophilic

More information

Conjugation is broken completely by the introduction of saturated (sp3) carbon:

Conjugation is broken completely by the introduction of saturated (sp3) carbon: Chapter 16 Conjugation, resonance, and dienes Conjugation relies on the partial overlap of p-orbitals on adjacent double or triple bonds. A common conjugated system involves 1,3-dienes, such as 1,3-butadiene.

More information

ALKENES AND ALKYNES REACTIONS A STUDENT WHO HAS MASTERED THE MATERIAL IN THIS SECTION SHOULD BE ABLE TO:

ALKENES AND ALKYNES REACTIONS A STUDENT WHO HAS MASTERED THE MATERIAL IN THIS SECTION SHOULD BE ABLE TO: ALKENES AND ALKYNES REACTINS A STUDENT W AS MASTERED TE MATERIAL IN TIS SECTIN SULD BE ABLE T: 1. Given the starting materials and reaction conditions, predict the products of the following reactions of

More information

CH 3 Addition to an alkene with Br 2. No reaction when an aromatic molecule is mixed with Br 2. No Reaction. + H Br

CH 3 Addition to an alkene with Br 2. No reaction when an aromatic molecule is mixed with Br 2. No Reaction. + H Br RADIALS Reactions with 2 : 2 3 Addition to an alkene with 2 2 No reaction when an aromatic molecule is mixed with 2 2 (in the dark) No Reaction 2 h (in the light) During a demonstration by Dr., the reactants

More information

SUMMARY OF ALKENE REACTIONS

SUMMARY OF ALKENE REACTIONS SUMMARY F ALKENE REACTINS Alkenes are primarily prepared by elimination reactions of molecules that contain good leaving groups attached to sp 3 carbons. Examples of such reactions are dehydrohalogenations

More information

Addition Reactions of Carbon-Carbon Pi Bonds - Part 1

Addition Reactions of Carbon-Carbon Pi Bonds - Part 1 Addition eactions of arbon-arbon Pi Bonds - Part 1 3 δ+ 2 δ 3 3 3 + 2 3 2 3 What Is an Addition eaction? Addition reaction: Atoms or groups are added to opposite ends of a pi bond. X Y Why should I study

More information

methyl RX example primary RX example secondary RX example secondary RX example tertiary RX example

methyl RX example primary RX example secondary RX example secondary RX example tertiary RX example ucleophilic Substitution & Elimination hemistry 1 eginning patterns to knowfor S and E eactions - horizontal and vertical templates for practice Example 1 - two possible perspectives (deuterium and tritium

More information

Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution Electrophilic Aromatic Substitution Electrophilic substitution is the typical reaction type for aromatic rings. Generalized electrophilic aromatic substitution: E E Electrophile Lewis acid: may be or neutral.

More information

Benzene Benzene is best represented as a resonance hybrid:

Benzene Benzene is best represented as a resonance hybrid: Electrophilic Aromatic Substitution (EAS) is a substitution reaction usually involving the benzene ring; more specifically it is a reaction in which the hydrogen atom of an aromatic ring is replaced as

More information

REACTIONS OF AROMATIC COMPOUNDS

REACTIONS OF AROMATIC COMPOUNDS A STUDENT SHOULD BE ABLE TO: REACTIONS OF AROMATIC COMPOUNDS 1. Predict the product(s) of Electrophilic Aromatic Substitution (EAS), Nucleophilic Aromatic Substitution (S N Ar) and Elimination-Addition

More information

Aromaticity and Reactions of Benzene

Aromaticity and Reactions of Benzene Aromaticity and eactions of Benzene ark College Benzene is a unique molecule it is highly unsaturated with 6 carbons and 6 hydrogens, it is planar, and has a high degree of symmetry. These features explain

More information

ALKENES AND ALKYNES REACTIONS

ALKENES AND ALKYNES REACTIONS A STUDENT SHULD BE ABLE T: ALKENES AND ALKYNES REACTINS 1. Given the starting materials and reaction conditions, predict the products of the following reactions of alkenes and alkynes. Regioselective Markovnikov

More information

Nucleophilic Substitution and Elimination

Nucleophilic Substitution and Elimination Nucleophilic Substitution and Elimination What does the term "nucleophilic substitution" imply? A nucleophile is an the electron rich species that will react with an electron poor species A substitution

More information

Chapter 15 Radical Reactions. Radicals are reactive species with a single unpaired electron, formed by

Chapter 15 Radical Reactions. Radicals are reactive species with a single unpaired electron, formed by Chapter 15 Radical Reactions Radicals are reactive species with a single unpaired electron, formed by homolysis of a covalent bond; a radical contains an atom that does not have an octet of electrons,

More information

CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway. CHAPTER 14 Substitution Reactions of Aromatic Compounds

CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway. CHAPTER 14 Substitution Reactions of Aromatic Compounds CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway "Organic Chemistry" by Maitland Jones, 4 th edition Chapter 14 Homework: 1, 2, 5, 7, 13, 19, 20, 23, 26, 27, 28, 30, 31, 34, 35, 36, 41, 46,

More information

Chapter 10. Conjugation in Alkadienes and Allylic Systems. Class Notes. B. The allyl group is both a common name and an accepted IUPAC name

Chapter 10. Conjugation in Alkadienes and Allylic Systems. Class Notes. B. The allyl group is both a common name and an accepted IUPAC name Chapter 10 Conjugation in Alkadienes and Allylic Systems Chapter 10 suggested problems: I. The allyl group Class Notes A. B. The allyl group is both a common name and an accepted IUPAC name 1. Allyl alcohol

More information

Final Examination, Organic Chemistry 1 (CHEM 2210) December 2000 Version *A* A. B. C. D.

Final Examination, Organic Chemistry 1 (CHEM 2210) December 2000 Version *A* A. B. C. D. Final Examination, rganic hemistry 1 (EM 2210) December 2000 Version *A* 1. What are the hybridization of, and the geometrical shape around, the nitrogen atom in the following molecule? N 3 3 A. sp, linear

More information

Electrophilic Aromatic Substitution Reactions

Electrophilic Aromatic Substitution Reactions Electrophilic Aromatic Substitution Reactions, Course Notes Archive, 1 Electrophilic Aromatic Substitution Reactions An organic reaction in which an electrophile substitutes a hydrogen atom in an aromatic

More information

Chapter 11. Free Radical Reactions

Chapter 11. Free Radical Reactions hapter 11 Free Radical Reactions A free radical is a species containing one or more unpaired electrons Free radicals are electron-deficient species, but they are usually uncharged, so their chemistry is

More information

C 2 H 5 L L LC 2 H 5 l max = 256 nm (e = 20,000) 283 nm (e = 5,100) CH 3 H 3 C. CH 3 i. B bimesityl l max = 266 nm (e = 700)

C 2 H 5 L L LC 2 H 5 l max = 256 nm (e = 20,000) 283 nm (e = 5,100) CH 3 H 3 C. CH 3 i. B bimesityl l max = 266 nm (e = 700) 750 CAPTER 6 TE CEITRY F BENZENE AND IT DERIVATIVE This hybridization allows one of its electron pairs to occupy a 2p orbital, which has the same size, shape, and orientation as the carbon 2p orbitals

More information

SUBSTITUTION REACTION CHARACTERISTICS. Sn1: Substitution Nucleophilic, Unimolecular: Characteristics

SUBSTITUTION REACTION CHARACTERISTICS. Sn1: Substitution Nucleophilic, Unimolecular: Characteristics SUBSTITUTION EATION AATEISTIS Sn2: Substitution cleophilic, Bimolecular: haracteristics 1) The 2 means Bimolecular (or 2 nd order) in the rate-determining (slow) step: rate = k [: - ] [-X] or rate = k

More information

Willem Elbers. October 9, 2015

Willem Elbers. October 9, 2015 S N 1 and S N 2 reactivity of 3 alkyl bromides Willem Elbers ctober 9, 2015 1 Abstract n this experiment, we investigate the relative reactivities of three alkyl bromides with increasing steric bulk. We

More information

Writing a Correct Mechanism

Writing a Correct Mechanism Chapter 2 1) Balancing Equations Writing a Correct Mechanism 2) Using Arrows to show Electron Movement 3) Mechanisms in Acidic and Basic Media 4) Electron rich Species: Nucleophile or Base? 5) Trimolecular

More information

Mass Spec - Fragmentation

Mass Spec - Fragmentation Mass Spec - Fragmentation An extremely useful result of EI ionization in particular is a phenomenon known as fragmentation. The radical cation that is produced when an electron is knocked out of a neutral

More information

Name. Department of Chemistry and Biochemistry SUNY/Oneonta. Chem 322 - Organic Chemistry II Examination #2 - March 14, 2005 ANSWERS

Name. Department of Chemistry and Biochemistry SUNY/Oneonta. Chem 322 - Organic Chemistry II Examination #2 - March 14, 2005 ANSWERS Name INSTRUTINS --- Department of hemistry and Biochemistry SUNY/neonta hem 322 - rganic hemistry II Examination #2 - March 14, 2005 ANSWERS This examination has two parts. Part I is in multiple choice

More information

Avg. 16.4 / 25 Stnd. Dev. 8.2

Avg. 16.4 / 25 Stnd. Dev. 8.2 QUIZ TREE Avg. 16.4 / 25 Stnd. Dev. 8.2 xidation of Alcohols with Chromium (VI): Jones xidation 2 Alcohols are oxidized by a solution of chromium trioxide in aqueous acetone (2), in the presence of an

More information

1. What is the hybridization of the indicated atom in the following molecule?

1. What is the hybridization of the indicated atom in the following molecule? Practice Final Exam, Chemistry 2210, rganic Chem I 1. What is the hybridization of the indicated atom in the following molecule? A. sp 3 B. sp 2 C. sp D. not hybridized 2. Name the functional groups in

More information

California State Polytechnic University, Pomona. Exam Points 1. Nomenclature (1) 30

California State Polytechnic University, Pomona. Exam Points 1. Nomenclature (1) 30 Chem 316 Final Exam Winter, 2008 Beauchamp ame: Topic Total Points Exam Points 1. omenclature (1) 30 Credit 2. Explanation of elative eactivities of Aromatic 20 Compounds or Carbonyl Compounds 3. eactions

More information

17.2 REACTIONS INVOLVING ALLYLIC AND BENZYLIC RADICALS

17.2 REACTIONS INVOLVING ALLYLIC AND BENZYLIC RADICALS 17. REACTINS INVLVING ALLYLIC AND BENZYLIC RADICALS 793 As Eq. 17. shows, the products derived from the reaction of water at the ring carbons are not formed. The reason is that these products are not aromatic

More information

Q.1 Draw out some suitable structures which fit the molecular formula C 6 H 6

Q.1 Draw out some suitable structures which fit the molecular formula C 6 H 6 Aromatic compounds GE 1 BENZENE Structure Primary analysis revealed benzene had an... empirical formula of and a molecular formula of 6 6 Q.1 Draw out some suitable structures which fit the molecular formula

More information

Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations SHORT ANSWER Exhibit 11-1 Circle your response in each set below. 1. Circle the least

More information

pk a Values for Selected Compounds

pk a Values for Selected Compounds Appendix A pk a Values for Selected ompounds ompound pk a ompound pk a I 10 Br 9 2 S 4 9 + 3 3 7.3 3 S 3 7 Br 4.0 4.2 3 4.3 2 N l 7 [( 3 ) 2 ] + 3.8 [ 3 2 ] + 2.5 3 + 1.7 3 S 3 1.2 + 3 N2 0.0 F 3 0.2 l

More information

Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution Electrophilic Aromatic Substitution Electrophilic Aromatic Substitution: a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring

More information

Chapter 6. Alkenes: Structure and Stability

Chapter 6. Alkenes: Structure and Stability hapter 6. Alkenes: Structure and Stability Steric Acid (saturated fatty acid) Linoleic Acid (unsaturated fatty acid) Degrees of unsaturation saturated hydrocarbon n 2n2 cycloalkane (1 ring) n 2n alkene

More information

SULFONATE AND INORGANIC ESTER DERIVATIVES OF ALCOHOLS

SULFONATE AND INORGANIC ESTER DERIVATIVES OF ALCOHOLS 0. ULFNATE AND INRGANIC ETER DERIVATIVE F ALCL 44 R 2 C L CR 2 carbocation Lewis acid base association X (halide ion) 2 $ R 2 C L CR 2 R R X C A C $ alkyl halide R R alkene $ $ Brønsted acid base reaction

More information

RESONANCE, USING CURVED ARROWS AND ACID-BASE REACTIONS

RESONANCE, USING CURVED ARROWS AND ACID-BASE REACTIONS RESONANCE, USING CURVED ARROWS AND ACID-BASE REACTIONS A STUDENT SHOULD BE ABLE TO: 1. Properly use curved arrows to draw resonance structures: the tail and the head of every arrow must be drawn in exactly

More information

for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency of the vibration

for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency of the vibration ! = 1 2"c k (m + M) m M wavenumbers! =!/c = 1/" wavelength frequency! units: cm 1 for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency

More information

INTDUCTIN T LEWIS ACID-BASE CEMISTY DEINITINS Lewis acids and bases are defined in terms of electron pair transfers. A Lewis base is an electron pair donor, and a Lewis acid is an electron pair acceptor.

More information

Table of contents. 44 and ketones Nucleophilic acyl substitution 48 Substitution reactions of carbonyl

Table of contents. 44 and ketones Nucleophilic acyl substitution 48 Substitution reactions of carbonyl Table of contents Subject Page # Introduction 1 Introductory concepts 2 Acids and bases 5 Alkane conformations 7 Stereochemistry 10 Elimination and substitution 14 Alcohols, ethers, epoxides 18 Alkenes

More information

Boston University Dresden Science Program ORGANIC CHEMISTRY CAS CH 203 Lecture

Boston University Dresden Science Program ORGANIC CHEMISTRY CAS CH 203 Lecture Boston University Dresden Science Program ORGANIC CHEMISTRY CAS CH 203 Lecture Instructor: Professor Wolf D. Habicher, Professor Claus Rüger Meeting Times Lectures: twice a week at 90 minutes each Discussions:

More information

Conjugation is broken completely by the introduction of saturated (sp 3 ) carbon:

Conjugation is broken completely by the introduction of saturated (sp 3 ) carbon: Conjugation. Conjugation relies on the partial overlap of p-orbitals on adjacent double or triple bonds. ne of the simplest conjugated molecules is 1,3-butadiene. Conjugation comes in three flavors, the

More information

ORGANIC CHEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions

ORGANIC CHEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions ORGANIC CEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions 1) Which of the following best represents the carbon-chlorine bond of methyl chloride? d d - d - d d d d - d - I II III IV V 2) Provide a detailed,

More information

Everything You Need to Know About Mechanisms. First rule: Arrows are used to indicate movement of electrons

Everything You Need to Know About Mechanisms. First rule: Arrows are used to indicate movement of electrons Everything You eed to Know About Mechanisms A) The orrect Use of Arrows to Indicate Electron Movement The ability to write an organic reaction mechanism properly is key to success in organic chemistry

More information

Anti-Markovnikov Addition of H-Br (How does the placement of Br differ in radical vs. polar addition of HBr to an alkene?)

Anti-Markovnikov Addition of H-Br (How does the placement of Br differ in radical vs. polar addition of HBr to an alkene?) hemactivity 21 Anti-Markovnikov Addition of 1 hemactivity 21 Anti-Markovnikov Addition of - (ow does the placement of differ in radical vs. polar addition of to an alkene?) Model 1: Radical Reactions of

More information

Chapter 7 Substitution Reactions

Chapter 7 Substitution Reactions Chapter 7 Substitution Reactions Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 7. Each of the sentences below appears

More information

But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens).

But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens). Reactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations the majority of which are either oxidation or reduction type reactions. Normally: Oxidation

More information

ammonium salt (acidic)

ammonium salt (acidic) Chem 360 Jasperse Ch. 19 otes. Amines 1 eactions of Amines 1. eaction as a proton base (Section 19-5 and 19-6) amine base -X (proton acid) a X ammonium salt (acidic) Mechanism: equired (protonation) everse

More information

A Grignard reagent formed would deprotonate H of the ethyl alcohol OH.

A Grignard reagent formed would deprotonate H of the ethyl alcohol OH. 216 S11-E2 Page 2 Name Key I. (9 points) Answer in the boxes below the following questions for the Grignard reagent C 3 -Mg. (1) (2 points) Is the carbon atom associated with magnesium electrophilic or

More information

Syllabus for General Organic Chemistry M07A- Fall 2013 Prof. Robert Keil

Syllabus for General Organic Chemistry M07A- Fall 2013 Prof. Robert Keil Syllabus for General Organic Chemistry M07A- Fall 2013 Prof. Robert Keil Textbook and Materials What you must buy: Organic Chemistry 4 th Ed. Janice G. Smith, McGraw Hill. (Older edition is fine) Chem

More information

Amines H 3 C H. CH 2 CH 3 ethylmethylamine. Nomenclature. 1 o : RNH 2, 2 o : RR'NH, 3 o : RR'R"N, 4 o (salt) RR'R"R'"N + R = alkyl or aryl

Amines H 3 C H. CH 2 CH 3 ethylmethylamine. Nomenclature. 1 o : RNH 2, 2 o : RR'NH, 3 o : RR'RN, 4 o (salt) RR'RR'N + R = alkyl or aryl Amines omenclature 1 o :, 2 o : 'H, 3 o : '", 4 o (salt) '"'" + = alkyl or aryl ommon names For simple amines name groups attached to alphabetically; use suffix -amine. H 3 H H 2 ethylmethylamine In complicated

More information

ALCOHOLS: Properties & Preparation

ALCOHOLS: Properties & Preparation ALLS: Properties & Preparation General formula: R-, where R is alkyl or substitued alkyl. Ar-: phenol - different properties. Nomenclature 1. ommon names: Name of alkyl group, followed by word alcohol.

More information

CHEM 208(Organic Chemistry I) Instructor: Dr. Niranjan Goswami. Tel: (618)545-3361. Email: Ngoswami@kaskaskia.edu. Web: www.kc.cc.il.

CHEM 208(Organic Chemistry I) Instructor: Dr. Niranjan Goswami. Tel: (618)545-3361. Email: Ngoswami@kaskaskia.edu. Web: www.kc.cc.il. CHEM 208(Organic Chemistry I) Instructor: Dr. Niranjan Goswami Tel: (618)545-3361 Email: Ngoswami@kaskaskia.edu Web: www.kc.cc.il.us/ngoswami CHEM 208 COURSE SYLLABUS KASKASKIA COLLEGE NAME TERM YEAR TEXT:

More information

Determining the Structure of an Organic Compound

Determining the Structure of an Organic Compound Determining the Structure of an Organic Compound The analysis of the outcome of a reaction requires that we know the full structure of the products as well as the reactants In the 19 th and early 20 th

More information

Carboxylic Acid Derivatives and Nitriles

Carboxylic Acid Derivatives and Nitriles Carboxylic Acid Derivatives and itriles Carboxylic Acid Derivatives: There are really only four things to worry about under this heading; acid chlorides, anhydrides, esters and amides. We ll start with

More information

Chapter 22 Carbonyl Alpha-Substitution Reactions

Chapter 22 Carbonyl Alpha-Substitution Reactions John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 22 Carbonyl Alpha-Substitution Reactions The α Position The carbon next to the carbonyl group is designated as being in the α position Electrophilic

More information

CH 3 CH 2 ONa + H 2 O. CH 3 CH 2 NH 2 + CH 3 OLi

CH 3 CH 2 ONa + H 2 O. CH 3 CH 2 NH 2 + CH 3 OLi rganic Chemistry Jasperse Acid- Practice Problems A. Identify each chemical as either an acid or a base in the following reactions, and identify conjugate relationships. -You should have one acid and one

More information

Prof. Dr. Burkhard König, Institut für Organische Chemie, Uni Regensburg 1. Enolate Chemistry

Prof. Dr. Burkhard König, Institut für Organische Chemie, Uni Regensburg 1. Enolate Chemistry Prof. Dr. Burkhard König, Institut für rganische Chemie, Uni Regensburg 1 1. Some Basics Enolate Chemistry In most cases the equilibrium lies almost completely on the side of the ketone. The ketone tautomer

More information

17.5 ALLYLIC AND BENZYLIC OXIDATION

17.5 ALLYLIC AND BENZYLIC OXIDATION 17.5 ALLYLI AND BENZYLI XIDATIN 803 Nuc d d Nuc d 2 3 2 overlap of 2p orbitals X d no p-orbital overlap X d (a) (b) Figure 17.2 Transition states for N 2 reactions at (a) an allylic carbon and (b) a nonallylic

More information

Substitution and Elimination Reactions. 7.1. Definitions. In an acid base reaction such as CH 3 CO 2 H + NH 3 CH 3 CO 2 + NH 4

Substitution and Elimination Reactions. 7.1. Definitions. In an acid base reaction such as CH 3 CO 2 H + NH 3 CH 3 CO 2 + NH 4 Substitution and Elimination Reactions. 7.1. Definitions. In an acid base reaction such as CH 3 CO 2 H + NH 3 CH 3 CO 2 + NH 4 +, the N acts as a nucleophile (Greek for loving the nucleus), the H acts

More information

Activation of Carbon-Hydrogen Bonds at Transition Metal Centers!

Activation of Carbon-Hydrogen Bonds at Transition Metal Centers! Activation of arbon-ydrogen Bonds at Transition Metal enters! Thanks to John Bercaw for many nice figures for this lecture! oxidative addition/reductive elimination [L n M q ] L n M q2 L n M q σ complex

More information

Chapter 2 Polar Covalent Bonds; Acids and Bases

Chapter 2 Polar Covalent Bonds; Acids and Bases John E. McMurry http://www.cengage.com/chemistry/mcmurry Chapter 2 Polar Covalent Bonds; Acids and Bases Javier E. Horta, M.D., Ph.D. University of Massachusetts Lowell Polar Covalent Bonds: Electronegativity

More information

Carbonyl Chemistry (12 Lectures)

Carbonyl Chemistry (12 Lectures) arbonyl hemistry (12 Lectures) Aim of ourse Professor Donna G. Blackmond d.blackmond@imperial.ac.uk tel. 41193 oom 639 1 To build upon elements of Dr E.. Smith s and Dr. D.. Braddocks s course. To introduce

More information

Resonance Structures Arrow Pushing Practice

Resonance Structures Arrow Pushing Practice Resonance Structures Arrow Pushing Practice The following is a collection of ions and neutral molecules for which several resonance structures can be drawn. For the ions, the charges can be delocalized

More information

Studying an Organic Reaction. How do we know if a reaction can occur? And if a reaction can occur what do we know about the reaction?

Studying an Organic Reaction. How do we know if a reaction can occur? And if a reaction can occur what do we know about the reaction? Studying an Organic Reaction How do we know if a reaction can occur? And if a reaction can occur what do we know about the reaction? Information we want to know: How much heat is generated? How fast is

More information

Acids and Bases: Molecular Structure and Acidity

Acids and Bases: Molecular Structure and Acidity Acids and Bases: Molecular Structure and Acidity Review the Acids and Bases Vocabulary List as needed. Tutorial Contents A. Introduction B. Resonance C. Atomic Radius D. Electronegativity E. Inductive

More information

Experiment 11. Infrared Spectroscopy

Experiment 11. Infrared Spectroscopy Chem 22 Spring 2010 Experiment 11 Infrared Spectroscopy Pre-lab preparation. (1) In Ch 5 and 12 of the text you will find examples of the most common functional groups in organic molecules. In your notebook,

More information

Reminder: These notes are meant to supplement, not replace, the textbook and lab manual. Electrophilic Aromatic Substitution notes

Reminder: These notes are meant to supplement, not replace, the textbook and lab manual. Electrophilic Aromatic Substitution notes Reminder: These notes are meant to supplement, not replace, the textbook and lab manual. Electrophilic Aromatic Substitution notes History and Application: The rate of a reaction directly impacts the commercial

More information

Carboxylic Acid Structure and Chemistry: Part 2

Carboxylic Acid Structure and Chemistry: Part 2 Principles of Drug Action 1, pring 2005, Carboxylic Acids Part 2 Carboxylic Acid tructure and Chemistry: Part 2 Jack Deuiter IV. eactions of the Carboxylic Acid eactions Depending on their overall structure,

More information

CHM4 Further Physical and Organic Chemistry

CHM4 Further Physical and Organic Chemistry GE 005 January Series abc Mark Scheme hemistry M4 Further Physical and rganic hemistry Mark schemes are prepared by the Principal Examiner and considered, together with the relevant questions, by a panel

More information

Name. (think carefully about the stereochemistry for this one) 2 Do you think this type of problem might show up on the final exam?

Name. (think carefully about the stereochemistry for this one) 2 Do you think this type of problem might show up on the final exam? Name 1 Chlorination of alkanes gives mixtures of products where chlorine has replaced H at every possible position. For example, chlorination of isobutane (CH 3 ) 3 CH produces a mixture of t- butyl chloride

More information

CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway

CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway "Organic Chemistry" by Maitland Jones, 4th edition Chapter 12 Homework: 1, 2, 4, 5, 6, 7, 15, 16, 17, 19, 21, 24, 26, 28, 29, 30, 38, 39, 44,

More information

SN2 Ionic Substitution Reactions

SN2 Ionic Substitution Reactions SN2 Ionic Substitution Reactions Chem 14D Winter 2005 SN2 Ionic Substitution Reactions Substitution can occur in organic compounds that have an electronegative atom or group bonded to an sp 3 hybridized

More information

Chapter 6 An Overview of Organic Reactions

Chapter 6 An Overview of Organic Reactions John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 6 An Overview of Organic Reactions Why this chapter? To understand organic and/or biochemistry, it is necessary to know: -What occurs -Why and

More information

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Nucleophilic Substitution smi97462_ch07.qxd 11/4/04 2:51 PM APTE Page 220 Alkyl alides and Nucleophilic Substitution Adrenaline (or epinephrine), a hormone secreted by the adrenal gland, increases blood pressure and heart rate,

More information

partial positive an acid is a hydrogen ion donor, or proton donor base is a hydrogen ion acceptor, or proton acceptor acidic protons acid base

partial positive an acid is a hydrogen ion donor, or proton donor base is a hydrogen ion acceptor, or proton acceptor acidic protons acid base INTRDUCTIN T INIC MECANISMS PART I: FUNDAMENTALS F BRNSTED-LWRY ACID-BASE CEMISTRY YDRGEN ATMS AND PRTNS IN RGANIC MLECULES - A hydrogen atom that has lost its only electron is sometimes referred to as

More information

Chemistry Notes for class 12 Chapter 13 Amines

Chemistry Notes for class 12 Chapter 13 Amines 1 P a g e Chemistry Notes for class 12 Chapter 13 Amines Amines constitute an important class of organic compounds derived by replacing one or more hydrogen atoms ofnh 3 molecule by alkyl/aryl group(s).

More information

23.7 ALKYLATION AND ACYLATION REACTIONS OF AMINES

23.7 ALKYLATION AND ACYLATION REACTIONS OF AMINES 3.7 ALKYLATIN AND ACYLATIN REACTIN F AMINE 1131 organic phase organic phase organic phase CH 3 (CH ) 6 CH Br CH 3 (CH ) 6 CH Br CH 3 (CH ) 6 CH CN R 4 P Br R 4 P CN R 4 P Br Na CN Na Br Na Br aqueous phase

More information

AROMATIC COMPOUNDS A STUDENT SHOULD BE ABLE TO:

AROMATIC COMPOUNDS A STUDENT SHOULD BE ABLE TO: A STUDENT SHULD BE ABLE T: ARMATIC CMPUNDS 1. Name benzene derivatives given the structures, and draw the structures given the names. This includes: Monosubstituted benzenes named as derivatives of benzene:

More information

Benzene and Aromatic Compounds

Benzene and Aromatic Compounds Benzene and Aromatic Compounds Benzene (C 6 H 6 ) is the simplest aromatic hydrocarbon (or arene). Benzene has four degrees of unsaturation, making it a highly unsaturated hydrocarbon. Whereas unsaturated

More information

passing through (Y-axis). The peaks are those shown at frequencies when less than

passing through (Y-axis). The peaks are those shown at frequencies when less than Infrared Spectroscopy used to analyze the presence of functional groups (bond types) in organic molecules The process for this analysis is two-fold: 1. Accurate analysis of infrared spectra to determine

More information

21.9 REDUCTION OF CARBOXYLIC ACID DERIVATIVES

21.9 REDUCTION OF CARBOXYLIC ACID DERIVATIVES 10 APTER 1 TE EMITRY F ARBXYLI AID DERIVATIVE TUDY GUIDE LIK 1.5 Esters and ucleophiles 1.17 Give the structure of the product in the reaction of each of the following esters with isotopically labeled

More information

Wittig Reaction - Phosphorous Ylides

Wittig Reaction - Phosphorous Ylides Wittig eaction - osphorous Ylides 3 P CC 3 3 C ylide tereoselectivity increases as the size of increases cis-olefin is derived from non-stabilized ylides Mechanism: Irreversible [22] cycloaddition P 3

More information

CHM220 Nucleophilic Substitution Lab. Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon*

CHM220 Nucleophilic Substitution Lab. Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon* CHM220 Nucleophilic Substitution Lab Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon* Purpose: To convert a primary alcohol to an alkyl bromide using an S N 2 reaction

More information

Principles of Drug Action 1, Spring 2005, Aromatics HYDROCARBON STRUCTURE AND CHEMISTRY: AROMATICS. Jack DeRuiter

Principles of Drug Action 1, Spring 2005, Aromatics HYDROCARBON STRUCTURE AND CHEMISTRY: AROMATICS. Jack DeRuiter I. Introduction YDOABON STUTUE AND EMISTY: AOMATIS Jack Deuiter ydrocarbons are organic compounds consisting of - and - bonds. arbon has a valence of four and thus requires four electrons or bonds to complete

More information

CHAPTER 7 ALCOHOLS, THIOLS, PHENOLS, ETHERS

CHAPTER 7 ALCOHOLS, THIOLS, PHENOLS, ETHERS CAPTER 7 ALCLS, TILS, PENLS, ETERS Several new functional groups are presented in this chapter. All of the functions are based on oxygen and sulfur in the sp 2 hybridized state. The functional groups contain

More information

IR Summary - All numerical values in the tables below are given in wavenumbers, cm -1

IR Summary - All numerical values in the tables below are given in wavenumbers, cm -1 Spectroscopy Data Tables Infrared Tables (short summary of common absorption frequencies) The values given in the tables that follow are typical values. Specific bands may fall over a range of wavenumbers,

More information

Experiment 6 Qualitative Tests for Alcohols, Alcohol Unknown, IR of Unknown

Experiment 6 Qualitative Tests for Alcohols, Alcohol Unknown, IR of Unknown Experiment 6 Qualitative Tests for Alcohols, Alcohol Unknown, I of Unknown In this experiment you are going to do a series of tests in order to determine whether or not an alcohol is a primary (1 ), secondary

More information

3.4 BRØNSTED LOWRY ACIDS AND BASES

3.4 BRØNSTED LOWRY ACIDS AND BASES 96 CAPTER 3 ACIDS AND BASES. TE CURVED-ARROW NOTATION and that the unshared electron pair (and negative charge) is shared equally by the two terminal carbons. C L C A C 1 allyl anion (c) Using the curved-arrow

More information

Guide to Solving Sophomore Organic Synthesis Problems

Guide to Solving Sophomore Organic Synthesis Problems Paul Bracher Chem 30 Synthesis eview Guide to Solving Sophomore rganic Synthesis Problems Disclaimer mission of a topic on this handout does not preclude that material from appearing on the final exam.

More information

The Aldol Condensation

The Aldol Condensation The Aldol ondensation Synthesis and Analysis of 2,3,4,5-Tetraphenylcyclopentadienone Yakety Sax Bennie ill theme song TPP eactions of Aldehydes and Ketones ' 1. Nucleophilic Addition. 2. Substitution at

More information

Homolytic vs. Heterolytic Fragmentation

Homolytic vs. Heterolytic Fragmentation omolytic vs. eterolytic Fragmentation Most organic transformations involve the movement of electron pairs (heterolytic reactions). There are a few important addition reactions, however, in which the electron

More information

ORGANIC CHEMISTRY I PRACTICE PROBLEMS FOR BRONSTED-LOWRY ACID-BASE CHEMISTRY

ORGANIC CHEMISTRY I PRACTICE PROBLEMS FOR BRONSTED-LOWRY ACID-BASE CHEMISTRY RGANIC CHEMISTRY I PRACTICE PRBLEMS FR BRNSTED-LWRY ACID-BASE CHEMISTRY 1. For each of the species below, identify the most acidic proton and provide the structure of the corresponding conjugate base.

More information

Chem 30A Fall 2004 QUIZ #2 (BLUE) Weds Nov 10th

Chem 30A Fall 2004 QUIZ #2 (BLUE) Weds Nov 10th Last Name ANSWER First Name KEY MI Student I Number: Circle the name of your TA: iscussion Section ay: Cari / Phil / Adam / eather Time: Total Score 35 / 30 Chem 30A Fall 2004 QUIZ #2 (BLUE) (15 Min) Weds

More information

Suggested solutions for Chapter 3

Suggested solutions for Chapter 3 s for Chapter PRBLEM Assuming that the molecular ion is the base peak (00% abundance) what peaks would appear in the mass spectrum of each of these molecules: (a) C5Br (b) C60 (c) C64Br In cases (a) and

More information

The dipolar nature of acids

The dipolar nature of acids I. Introduction arboxylic Acid Structure and hemistry: Part 1 Jack Deuiter arboxylic acids are hydrocarbon derivatives containing a carboxyl () moiety. ecall that carbon has four valence electrons and

More information

CORK INSTITUTE OF TECHNOLOGY INSTITIÚID TEICNEOLAÍOCHTA CHORCAÍ

CORK INSTITUTE OF TECHNOLOGY INSTITIÚID TEICNEOLAÍOCHTA CHORCAÍ CORK INSTITUTE OF TECHNOLOGY INSTITIÚID TEICNEOLAÍOCHTA CHORCAÍ Module Title: Topics in Organic Chemistry Module Code: CHEO 7003 School : Science Programme Title: Bachelor of Science in Analytical & Pharmaceutical

More information