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

Reaction 2. Radical addition of hydrogen bromide (HBr) to alkenes. (NOT COVERED THIS TIME)

Reaction 2. Radical addition of hydrogen bromide (HBr) to alkenes. (NOT COVERED THIS TIME) http://courses.chem.psu.edu/chem38/reactions/reactions.html Reaction 1. Electrophilic addition of hydrogen halides (HX) to alkenes. HCl, HBr in ether KI + H 3 PO 4 room temperature electrophilic addition

More information

Ozonolysis of Alkenes

Ozonolysis of Alkenes zonolysis of Alkenes 1 When 2-methyl-2-pentene reacts with ozone, the initial 1,2,3-trioxolane product is 144, but this rearranges to ozonide 145. If 145 is treated with hydrogen peroxide as above, one

More information

Double bonds separated by more than one single bond are isolated. Compounds with isolated double bonds have the same chemical properties as alkenes.

Double bonds separated by more than one single bond are isolated. Compounds with isolated double bonds have the same chemical properties as alkenes. DIENES Dienes are alkenes with 2 double bonds. IUPA: Same as alkene, but change -ene to -adiene and use two numbers to locate the two double bonds (number from the end of the chain which makes the smaller

More information

Lecture Notes Chem 51B S. King. Chapter 18 Electrophilic Aromatic Substitution

Lecture Notes Chem 51B S. King. Chapter 18 Electrophilic Aromatic Substitution Lecture otes Chem 51B S. King Chapter 18 Electrophilic Aromatic Substitution I. Electrophilic Aromatic Substitution The most characteristic reaction of aromatic compounds is electrophilic aromatic substitution,

More information

Chapter 8: Chemistry of Alkynes (C n H 2n-2 )

Chapter 8: Chemistry of Alkynes (C n H 2n-2 ) hapter 8: hemistry of Alkynes ( n 2n-2 ) Bonding & hybridization Both are sp-hybridized Bond angles = 180 o 1 σ + 2 π bonds Linear around lassification R R R' σ bond energy: 88 kcal/mol π bond energy:

More information

Stability of vinyl C+ is about the same as H 3 C+. NOT ASSISTED!

Stability of vinyl C+ is about the same as H 3 C+. NOT ASSISTED! rganic hemistry Interactive Notes hapter 8: Alkynes Naming Alkynes Structure ommon Name IUPA Acetylene ethyne methyl acetylene propyne dimethyl acetylene -butyne ethyl acetylene -butyne =- as substituent

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

Protonation. favored H 3 O + R O O H

Protonation. favored H 3 O + R O O H arboxylic Acids arboxylic acids have one property that distinguishes them from most other organic compounds they re acidic. Now not as acidic as fuming sulfuric acid, but still pretty darned acidic. The

More information

KOT 222 ORGANIC CHEMISTRY II CHAPTER 17. REACTIONS of AROMATIC COMPOUNDS

KOT 222 ORGANIC CHEMISTRY II CHAPTER 17. REACTIONS of AROMATIC COMPOUNDS KOT 222 ORGANIC CEMISTRY II CAPTER 17 REACTIONS of AROMATIC COMPOUNDS 1 Electrophilic Aromatic Substitution Substitution of an electrophile for a proton on the aromatic ring. benzene s pi electrons are

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

Chapter 13. Conjugated Unsaturated Systems. Conjugation, Resonance and Dienes. Conjugation, Resonance and Dienes. What is the conjugation?

Chapter 13. Conjugated Unsaturated Systems. Conjugation, Resonance and Dienes. Conjugation, Resonance and Dienes. What is the conjugation? Chapter 13 Conjugation, Resonance and Dienes What is the conjugation? Conjugation occurs whenever p orbitals are located on three or more adjacent atoms. Conjugated Unsaturated Systems The four p orbitals

More information

Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution. Let us look at bromination: δ+ δ Br Br FeBr 3 Br Br FeBr 3

Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution. Let us look at bromination: δ+ δ Br Br FeBr 3 Br Br FeBr 3 Chapter 16: Chemistry of Benzene: lectrophilic Aromatic Substitution lectrophilic positively charged species searching for electron density Aromatic benzene ring with a high electron density Substitution

More information

From alkanes Radical halogenation

From alkanes Radical halogenation From alkanes Radical halogenation 4 2 300 or h! Alkyl alides from Alkanes 3 form, where comes from 2 form, where comes from methane and comes from 2 break bond break bond what is the role of heating or

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

Benzene does not undergo electrophilic addition. It undergoes electrophilic aromatic substitution maintaining the aromatic core

Benzene does not undergo electrophilic addition. It undergoes electrophilic aromatic substitution maintaining the aromatic core Substitution Reactions of Benzene and Its Derivatives Benzene does not undergo electrophilic addition It undergoes electrophilic aromatic substitution maintaining the aromatic core Electrophilic aromatic

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

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

Reaction Coordinate Diagrams for the Two Benzene Reactions

Reaction Coordinate Diagrams for the Two Benzene Reactions Electrophilic Addition vs. Substitution ( LEAVES!) Electrophilic Aromatic Substitution δ δ E E Y Y Reaction Coordinate Diagrams for the Two Benzene Reactions δ δ E E Y Y Electrophilic aromatic substitutions

More information

CHEMICAL REACTIVITY AND MECHANISMS, AND SUBSTITUTION REACTIONS

CHEMICAL REACTIVITY AND MECHANISMS, AND SUBSTITUTION REACTIONS EMIAL REATIVITY AND MEANISMS, AND SUBSTITUTION REATIONS A STUDENT SOULD BE ABLE TO: 1. Understand the concepts of: enthalpy, entropy, free energy, equilibrium and kinetics. Given a reaction coordinate

More information

Organic Chemistry Practice Exam #4

Organic Chemistry Practice Exam #4 rganic Chemistry 32-235 Practice Exam #4 Part 1: 1. The correct IUPAC name for the following structure is. C 2 CC 2 C C 2 5-hexen-3-ol 3-hydroxy-5-hexene (E) 4-hydroxy-1-hexene 1-hexen-4-ol (D) Isohexen-3-ol,

More information

Chapter 17: Reactions of Aromatic Compounds

Chapter 17: Reactions of Aromatic Compounds Chapter 17: Reactions of Aromatic Compounds Electrophilic aromatic substitution (17-1) Most common (normal) reaction of aromatics HNO 3 H 2 SO 4 NO 2 + H2O 452 Similar to alkenes, benzene (aromatics) has

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

Review of an Alkene. Therefore even though a carbon-carbon σ bond rarely reacts, the π bond reacts readily

Review of an Alkene. Therefore even though a carbon-carbon σ bond rarely reacts, the π bond reacts readily Review of an Alkene Two sp 2 hybridized carbon atoms 1 σ bond 83 Kcal/mol 1 π bond 63 Kcal/mol A π bond is much lower in energy than a σ bond Therefore even though a carbon-carbon σ bond rarely reacts,

More information

6.10 Acid-Catalyzed Hydration of Alkenes. Acid-Catalyzed Hydration of Alkenes

6.10 Acid-Catalyzed Hydration of Alkenes. Acid-Catalyzed Hydration of Alkenes Acid-atalyzed ydration of Alkenes 6.10 Acid-atalyzed ydration of Alkenes + O O reaction is acid catalyzed; typical hydration medium is 50% 2 SO 4-50% 2 O Follows Markovnikov's Rule Follows Markovnikov's

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

The Structure of Alkynes

The Structure of Alkynes Synthesis of Acetylene Alkynes eating coke with lime in an electric furnace to forms calcium carbide. Then drip water on the calcium carbide. 3 ao a 2 coke lime O * a 2 2 2 O a(o) 2 *This reaction was

More information

Carbocations are electrophiles, and can therefore be useful reagents for forming new C-C bonds in EAS processes.

Carbocations are electrophiles, and can therefore be useful reagents for forming new C-C bonds in EAS processes. 1 (Continuation of Chapter 17 ) VIII. Friedel-Crafts Alkylation Carbocations are electrophiles, and can therefore be useful reagents for forming new C-C bonds in EAS processes. Friedal and Craft demonstrated

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

19.2 Halogenation 4/18/2012. Is the reaction substitution, elimination, addition or pericyclic?

19.2 Halogenation 4/18/2012. Is the reaction substitution, elimination, addition or pericyclic? 19.1 Introduction to Electrophilic Aromatic Substitution In Chapter 18, we saw how aromatic C=C double bonds are less reactive than typical alkene double bonds. Consider a bromination reaction: 19.1 Introduction

More information

Learning Guide for Chapter 11 - Alkynes

Learning Guide for Chapter 11 - Alkynes Learning Guide for Chapter 11 - Alkynes Introduction to s - p 1 ybridization and geometry, Reactivity, Types of s, Cyclic s, Physical properties, Spectroscopy, Acidity, Natural occurrence and uses Nomenclature

More information

ORG CHEM II 2nd EXAM NAME

ORG CHEM II 2nd EXAM NAME G EM II 2nd EXAM AME 1) Which of the following combinations is correct? Aldehydes... i. are more reactive than ketones towards nucleophiles ii. are more easily oxidized than ketones iii. are less reactive

More information

2. Determine the product that would be formed from the S N 2 reaction of a. (R)-2-bromobutane and hydroxide ion (aprotic solvent) (S)-2-butanol

2. Determine the product that would be formed from the S N 2 reaction of a. (R)-2-bromobutane and hydroxide ion (aprotic solvent) (S)-2-butanol 1. Define and understand the following terms. (I will go over these if you have questions, but will expect that you have attempted to understand them on your own.) a. yperconjugation b. Basicity c. Nucleophile

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

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

Chapter 14 Conjugated Compounds and Ultraviolet Spectroscopy

Chapter 14 Conjugated Compounds and Ultraviolet Spectroscopy John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 14 Conjugated Compounds and Ultraviolet Spectroscopy Conjugated and Nonconjugated Dienes Compounds can have more than one double or triple bond

More information

Alcohols (R-OH) and Alkyl halides R-X (X = F, Cl, Br, I) Alcohols. Suffix:

Alcohols (R-OH) and Alkyl halides R-X (X = F, Cl, Br, I) Alcohols. Suffix: Alcohols (R-O) and Alkyl halides R-X (X = F, Cl,, I) Alcohols Alcohols contain a R-O functional group. Primary, secondary or tertiary? O O O Nomenclature: Suffix: numbering scheme: The number locating

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

Chapter 18. Reactions of Aldehydes and Ketones

Chapter 18. Reactions of Aldehydes and Ketones hapter 18. Reactions of 1 Aldehydes and Ketones Reaction of a nucleophile with an aldehyde or ketone gives an alkoxide, and subsequent hydrolysis leads to an alcohol. This chapter will define differences

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

Chapter 12 Electrophilic and Nucleophilic Aromatic Substitution

Chapter 12 Electrophilic and Nucleophilic Aromatic Substitution Chapter 12 Electrophilic and Nucleophilic Aromatic Substitution CHAPTER 12 Electrophilic and Nucleophilic Aromatic Substitution Aromatic compounds may undergo substitution reactions. Electrophilic aromatic

More information

Reactions of Aromatic Compounds

Reactions of Aromatic Compounds 2-1 Reactions of Aromatic Compounds 15.1 2-2 lectrophilic Aromatic Substitution Reactions Aromatic hydrocarbons (= arenes) undergo a substitution reaction with electrophiles: + catalyst + xample: omination

More information

Alkynes and Their Reactions

Alkynes and Their Reactions Alkynes and Their Reactions Naming Alkynes Alkynes are named in the same general way that alkenes are named. In the IUPAC system, change the ane ending of the parent alkane name to the suffix yne. Choose

More information

Aromatic compounds are less reactive than many other molecules because of their stability

Aromatic compounds are less reactive than many other molecules because of their stability rganic Chemistry otes by Jim Maxka C 16: Reactions of Aromatic Compounds Topics: Aromatic compounds are less reactive than many other molecules because of their stability Formation of very T electrophiles

More information

Alkynes: An Introduction to Organic Synthesis

Alkynes: An Introduction to Organic Synthesis Alkynes: An Introduction to Organic Synthesis Alkynes Hydrocarbons that contain carbon-carbon triple bonds Acetylene, the simplest alkyne is produced industrially from methane and steam at high temperature

More information

Alkynes: An Introduction to Organic Synthesis. Based on McMurry s Organic Chemistry, 6 th edition, Chapter 8

Alkynes: An Introduction to Organic Synthesis. Based on McMurry s Organic Chemistry, 6 th edition, Chapter 8 Alkynes: An Introduction to Organic Synthesis Based on McMurry s Organic Chemistry, 6 th edition, Chapter 8 Alkynes! Hydrocarbons that contain carbon-carbon triple bonds! Acetylene, the simplest alkyne

More information

Chemistry 232 Summer 2016 Quiz 2a

Chemistry 232 Summer 2016 Quiz 2a 1 Chemistry 232 Summer 2016 Quiz 2a KEY Name: (Please print, surname first) ID: Do all questions. Time available: 20 min. Total available marks: 20. Score for this quiz: Answers written partially or completely

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

Where R = alkyl group, Nu = nucleophile and L = leaving group.

Where R = alkyl group, Nu = nucleophile and L = leaving group. Organic Chemistry (CEM311) Fall 2005 Dr. Robert F. Dias 9. SUBSTITUTIONS: S N 1, S N 2 2 basic kinds of substitution reactions: S N 2 = Substitution Nucleophillic Bimolecular S N 1 = Substitution Nuclophillic

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

Electrophilic Aromatic Substitution Part 1

Electrophilic Aromatic Substitution Part 1 Electrophilic Aromatic Substitution Part 1 Generic reaction: Optional reading: OCATSA Email instructor for access Introduction Fact: Alkenes undergo electrophilic addition Addition reaction: Increases

More information

Nu: Br Br Nu + Br + Br -

Nu: Br Br Nu + Br + Br - 10.1. Addition of X 2 to Alkenes and Alkynes to give 1,2- Dihalides. We have mentioned that alkenes and alkynes are not sufficiently good nucleophiles to react with alkyl halides. owever, they are sufficiently

More information

508 CHAPTER TWELVE Reactions of Arenes: Electrophilic Aromatic Substitution O O BF 3. Acetic anhydride H H

508 CHAPTER TWELVE Reactions of Arenes: Electrophilic Aromatic Substitution O O BF 3. Acetic anhydride H H 508 CAPTR TWLV Reactions of s: lectrophilic Aromatic Substitution C3 CCC 3 BF 3 CC C 3 C 3 Furan Acetic anhydride 2-Acetylfuran (75 92%) Acetic acid The regioselectivity of substitution in furan is explained

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

Reactions of Aromatic Compounds

Reactions of Aromatic Compounds Reactions of Aromatic Compounds Aromatic compounds are stabilized by this aromatic stabilization energy Due to this stabilization, normal S N 2 reactions observed with alkanes do not occur with aromatic

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

It does not react N.R.

It does not react N.R. Benzene versus yclohexene versus yclohexadiene 1 l l cyclohexene l l cyclohexadiene l Expect this to react similarly "cyclohexatriene" It does not react l N.R. benzene Benzene is resonance stabilized,

More information

very strong bases very strong nucleophiles

very strong bases very strong nucleophiles hapter 14: rganometallic ompounds - eagents with carbon-metal bonds 14.1: rganometallic Nomenclature (please read) 3 -Li Butyllithium Mg vinylmagnesium bromide ( 3 ) u - Li Dimethylcopper lithium 14.:

More information

Alkynes contain a C C triple bond

Alkynes contain a C C triple bond Chapter 8: Alkynes: an introduction to organic synthesis Alkynes contain a C C triple bond Acetylene: H-C C-H is the common name for ethyne, used as a torch fuel Alkyne nomenclature follows normal hydrocarbon

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

So far we have mostly limited our good leaving groups to the very similar, stable halide anions, Cl -, Br - and I -.

So far we have mostly limited our good leaving groups to the very similar, stable halide anions, Cl -, Br - and I -. Extending the - pectrum: Making Alcohols () into eactive and E eactants (Two Ways) o far we have mostly limited our good leaving groups to the very similar, stable halide anions, -, Br - and I -. 1 Base

More information

Worksheet Addition reactions

Worksheet Addition reactions Worksheet Addition reactions The presence of electrons in alkenes allows addition reactions to take place. In general: In each case, the bond is broken and the e - are used to form a new bond in the product

More information

An alkyne is a hydrocarbon that contain a Carbon carbon triple bond. Acetylene, the simplest alkyne, widely used in industry for the synthesis of

An alkyne is a hydrocarbon that contain a Carbon carbon triple bond. Acetylene, the simplest alkyne, widely used in industry for the synthesis of Alkynes An alkyne is a hydrocarbon that contain a Carbon carbon triple bond. Acetylene, the simplest alkyne, widely used in industry for the synthesis of acetaldehyde, acetic acid, vinyl chloride O O H

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

Reaction Coordinate Diagrams for the Two Benzene Reactions

Reaction Coordinate Diagrams for the Two Benzene Reactions Organic Chemistry 8 th Edition Paula Yurkanis Bruice Aromatic compounds such as benzene undergo electrophilic aromatic substitution reactions: Chapter 18 Reactions of Benzene and Substituted Benzenes Cap.

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

Lecture 8. Friedel-Crafts reaction: Mechanism: Carbocation is the reactive electrophile. AlCl4- picks up a proton.

Lecture 8. Friedel-Crafts reaction: Mechanism: Carbocation is the reactive electrophile. AlCl4- picks up a proton. New Section 3 Page 1 2:37 PM Friedel-Crafts reaction: Mechanism: Carbocation is the reactive electrophile. AlCl4- picks up a proton. Limitations come from the mechanism: Carbocationic intermediates prone

More information

Chapter 13 Alkenes and Alkynes

Chapter 13 Alkenes and Alkynes hapter 13 Alkenes and Alkynes Types of Bonds Alkanes and haloalkanes consist of atoms held together by bonds. These can also be called sigma bonds (σ bonds) which means that the orbitals of each atom overlap

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

Benzene benzene aromatic hydrocarbons aromatic not not

Benzene benzene aromatic hydrocarbons aromatic not not Benzene 1 NT 87 90 ompound 87 has the formula 6 6, is known as benzene, and it is a hydrocarbon derived from petroleum distillates. Benzene is the parent compound for a class of compounds known as aromatic

More information

Chapter 17 Alcohols and Phenols

Chapter 17 Alcohols and Phenols John E. McMurry http://www.cengage.com/chemistry/mcmurry Chapter 17 Alcohols and Phenols Alcohols and Phenols Alcohols contain an OH group connected to a saturated C (sp 3 ) They are important solvents

More information

AROMATICITY. Chapter 8 REACTIONS OF BENZENE ORGANIC CHEMISTRY, 2 ND EDITION PAULA YURKANIS BRUICE

AROMATICITY. Chapter 8 REACTIONS OF BENZENE ORGANIC CHEMISTRY, 2 ND EDITION PAULA YURKANIS BRUICE ORGANIC CHEMISTRY, 2 ND EDITION PAULA YURKANIS BRUICE Chapter 8 AROMATICITY REACTIONS OF BENZENE RAED M. AL-ZOUBI, ASSISTANT PROFESSOR OF CHEMISTRY DEPARTMENT OF CHEMISTRY - N 4 L 0 JORDAN UNIVERSITY OF

More information

CHE Organic Chemistry Exam 1 January 31, 1996

CHE Organic Chemistry Exam 1 January 31, 1996 E 232-001 rganic hemistry Exam 1 January 31, 1996 Name KEY Student ID No. Before you begin this exam: First: You are allowed to have a calculator and a simple model set at your seat. Please put away all

More information

Chemistry 222--Spring Third Problem Set Due 5/1/02 H H HO OH. H Ether C H

Chemistry 222--Spring Third Problem Set Due 5/1/02 H H HO OH. H Ether C H hemistry 222--Spring 2002--Third Problem Set Due 5/1/02 nswers Part. For the following reactions, give the predominant product. learly show stereochemistry when appropriate (that is, draw a structure that

More information

CHEMISTRY 263 Module7. Hydrogenation of Alkenes Text Sections: Homework Chapter7: Module8. Alkenes and Alkynes II: Addition reactions

CHEMISTRY 263 Module7. Hydrogenation of Alkenes Text Sections: Homework Chapter7: Module8. Alkenes and Alkynes II: Addition reactions 1 CHEMISTRY 263 Module7. Hydrogenation of Alkenes The Function of the Catalyst - Syn and anti- addition Hydrogenation of Alkynes - Syn- addition of hydrogen: Synthesis of cis-alkenes - Anti addition of

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

Look for absorption bands in decreasing order of importance:

Look for absorption bands in decreasing order of importance: Infrared spectra: It is important to remember that the absence of an absorption band can often provide more information about the structure of a compound than the presence of a band. Be careful to avoid

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

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

Vibrational Spectroscopy Functional Groups

Vibrational Spectroscopy Functional Groups hem 325 Vibrational Spectroscopy Functional roups Bonds to - single N- single - single egions of the I Spectrum The I spectrum normally spans the 4000 cm -1 to 400 cm -1 range (2500 nm to 25000 nm). This

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

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

Carbocations Based on a Fall 2001 Chemistry 30BH Honors project by Patricia Young

Carbocations Based on a Fall 2001 Chemistry 30BH Honors project by Patricia Young arbocations Based on a Fall 2001 hemistry 30B onors project by Patricia Young Tutorial ontents A. Introduction B. arbocation lassification. arbocation Stability D. arbocation Formation E. Three Fates of

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

24.6 Sources of Phenols

24.6 Sources of Phenols 24.6 Sources of Phenols Phenol is an important industrial chemical. Major use is in phenolic resins for adhesives and plastics. Annual U.S. production is about 4 billion pounds per year. Industrial Preparations

More information

Carboxylic Acids When a carbonyl carbon also bears a hydroxyl group, then these compounds are appreciably acidic, and are called carboxylic acids.

Carboxylic Acids When a carbonyl carbon also bears a hydroxyl group, then these compounds are appreciably acidic, and are called carboxylic acids. Carboxylic Acids When a carbonyl carbon also bears a hydroxyl group, then these compounds are appreciably acidic, and are called carboxylic acids. R Carboxylic acids are classified according to the substituent

More information

ORGANIC CHEMISTRY I PRACTICE EXERCISE Elimination Reactions and Alkene Synthesis

ORGANIC CHEMISTRY I PRACTICE EXERCISE Elimination Reactions and Alkene Synthesis RGANIC CEMISTRY I PRACTICE EXERCISE Elimination Reactions and Alkene Synthesis ) ne of the products that results when -bromo-,-dimethylcyclopentane is heated in ethanol is shown below. Give a mechanism

More information

Part A: Electrophilic Aromatic Substitution (What products are formed when a strong electrophile is added to benzene?)

Part A: Electrophilic Aromatic Substitution (What products are formed when a strong electrophile is added to benzene?) hemactivity 29 lectrophilic Aromatic Substitution 1 hemactivity 29 Part A: lectrophilic Aromatic Substitution (What products are formed when a strong electrophile is added to benzene?) Model 1: (review)

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

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

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

CARBOXYLIC ACIDS AND THEIR DERIVATIVES

CARBOXYLIC ACIDS AND THEIR DERIVATIVES ARBXYLI AIDS AND TEIR DERIVATIVES A STUDENT SULD BE ABLE T: 1. Give the IUPA name given the structure, and draw the structure given the name, of carboxylic acids and their metal salts, acyl chlorides,

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

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 11 Alkynes 1

Chapter 11 Alkynes 1 Chapter 11 Alkynes 1 Alkynes Introduction Structure and Bonding Alkynes contain a carbon carbon triple bond. Terminal alkynes have the triple bond at the end of the carbon chain so that a hydrogen atom

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

Chapter 6 Alkenes I. IUPAC Rules for Alkene and Cycloalkene Nomenclature

Chapter 6 Alkenes I. IUPAC Rules for Alkene and Cycloalkene Nomenclature hapter 6 Alkenes I Naming Alkenes General Rule: replace ane with ene. No. of arbons IUPA Name ommon Name Formula n 2n Structure 2 Ethane ethylene 2 4 2 = 2 3 Propene propylene 3 6 2 = 3 4 1-Butene butylene

More information