Friedel Crafts Acylation

Save this PDF as:
 WORD  PNG  TXT  JPG

Size: px
Start display at page:

Download "Friedel Crafts Acylation"

Transcription

1 Friedel Crafts Acylation An acyl chloride or an acid anhydride is the source of the acyl group. A Lewis acid (AlCl 3 ) is required.

2 The Mechanism for Friedel Crafts Acylation The electrophile adds to the benzene ring. A base in the reaction mixture removes the proton from the carbon that formed the bond with the electrophile.

3 Generating the Electrophile for Friedel Crafts Acylation The acylium ion is the electrophile.

4 AlCl 3 Reacts with the Product of Friedel Crafts Acylation More than one equivalent of AlCl3 must be used in a Friedel Crafts acylation. AlCl 3 forms a complex with the carbonyl group in the product. Water is added to the reaction mixture to liberate the product from the complex.

5 The Gatterman Koch Reaction Benzaldehyde cannot be made by a Friedel Crafts acylation because the needed acyl chloride (formyl chloride) is unstable. Formyl chloride is generated in the reaction mixture.

6 Friedel Crafts Alkylation An alky halide is the source of the alkyl group. A Lewis acid (AlCl 3 ) is required.

7 Generation of the Electrophile for Friedel Crafts Alkylation A carbocation is the electrophile.

8 The Mechanism for Friedel Crafts Alkylation The electrophile adds to the benzene ring. A base in the reaction mixture removes the proton from the carbon that formed the bond with the electrophile.

9 There are Limits to Friedel Crafts Alkylation The alkylated benzene product is more reactive than benzene. Therefore, a large excess of benzene is needed to avoid multiple alkylations of the ring.

10 Carbocation Rearrangement Leads to an Undesired Product

11 Carbocation Rearrangement Leads to an Undesired Product

12 Should We Draw Primary Carbocations? Friedel Crafts alkylation mechanisms are written as if a primary carbocation is formed, although we know that primary carbocations are too unstable to be formed. A true primary carbocation is never formed. Instead, an incipient carbocation is formed.

13 Putting a Straight Chain Alkyl Group on a Ring Add the correct number of carbons with a Friedel Crafts acylation reaction. Reduce the carbonyl group to a methylene group. (Catalytic hydrogenation reduces only a carbonyl group adjacent to a benzene ring.)

14 Other Ways to Convert a Carbonyl Group to a Methylene Group

15 The Mechanism for the Wolff Kishner Reduction The ketone forms a hydrazone following the mechanism for imine formation. A hydroxide ion removes a proton from the weakly acidic NH 2 group. Reprotonation occurs at carbon. Another deprotonation, loss of N 2, and reprotonation forms the product.

16 Coupling Reactions Can Be Used to Put a Straight Chain Alkyl Group on a Benzene Ring

17 Why it is Important to Have More Than One Way to Carry Out a Reaction Catalytic hydrogenation reduces aromatic nitro groups and carbonyl groups. Wolff Kishner reduction reduces only the carbonyl group.

18 Substituents on a Benzene Ring Can Be Chemically Changed Bromine will selectively substitute for a benzylic hydrogen in a radical substitution reaction. A halogen at the benzylic position can lead to substitution or elimination.

19 Substitution at the Benzylic Position S N 1 and S N 2 reactions can lead to a wide variety of substituted benzenes.

20 Elimination at the Benzylic Position E1 and E2 reactions lead to alkene-substituted benzenes. (A bulky base is used to encourage elimination over substitution.)

21 Unsaturated Substituents Can Be Reduced

22 The Benzene Ring is Reduced Only at High Temperature and Pressure

23 Alkyl Substituents are Oxidized to Carboxyl Groups

24 Alkyl Substituents Without Benzylic Hydrogens Cannot Be Oxidized (The first step in the oxidation reaction is removal of a benzylic hydrogen.)

25 Nitro Substituents are Reduced by Catalytic Hydrogenation

26 Nomenclature of Disubstituted Benzenes The relative positions of two substituents can be indicated by numbers or by prefixes. ortho = adjacent meta = separated by one carbon para = opposite one another

27 Nomenclature of Disubstituted Benzenes The substituents are listed in alphabetical order. The first substituent is given the 1-position. The ring is numbered to give the second substituent the lowest possible number.

28 Nomenclature of Disubstituted Benzenes Some substituents can be incorporated into a name. An incorporated substituent is given the 1-position. With a second substituent, methylbenzene is used rather than toluene.

29 Nomenclature of Disubstituted Benzenes Some disubstituted benzenes have both substituents incorporated into the name.

30 Nomenclature of Polysubstituted Benzenes List substituents alphabetically and number so that the lowest possible numbers result. An incorporated substituent is given the 1-position.

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

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

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

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

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

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

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

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

Benzene and aromatic compounds (McMurry Ch. 15 & 16) The resonance hybrid model explains these properties of benzene:

Benzene and aromatic compounds (McMurry Ch. 15 & 16) The resonance hybrid model explains these properties of benzene: Benzene and aromatic compounds (McMurry Ch. 15 & 16) C 6 H 6 is an unusually stable molecule that does NOT react like alkenes do A model was proposed by Kekule in 1865: The resonance hybrid model explains

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

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

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

Organic Chemistry Specific Name Reactions

Organic Chemistry Specific Name Reactions Organic Chemistry Specific Name Reactions Sandmeyer Reaction Class XII The Cl, Br and CN nucleophiles can easily be introduced in the benzene ring of benzene diazonium salt in the presence of Cu(I) ion.

More information

Study Guide Chapters 19-20 Alkanes, Alkenes and Alkynes

Study Guide Chapters 19-20 Alkanes, Alkenes and Alkynes Study Guide Chapters 19-20 Alkanes, Alkenes and Alkynes 1) Carbon-Carbon Bonding in Alkanes (C-C), Alkenes (C=C) and Alkynes (C C). Understand the hybridization of atomic orbitals (ground state promotion

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

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

Under acidic conditions, carbonyl compounds are protonated on O first, then weak base deprotonates at the α-c to give enol.

Under acidic conditions, carbonyl compounds are protonated on O first, then weak base deprotonates at the α-c to give enol. Substitution reactions of carbonyl compounds at the α-position Carbonyl compounds are acidic at α-c (e.g. C 2 C ); this is because of the electrophilic nature of carbonyl C= bond. The pka values of simple

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

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

AP Chemistry Chapter 22 - Organic and Biological Molecules

AP Chemistry Chapter 22 - Organic and Biological Molecules AP Chemistry Chapter - Organic and Biological Molecules.1 Alkanes: Saturated Hydrocarbons A. Straight-chain Hydrocarbons 1. Straight-chain alkanes have the formula C n H n+. Carbons are sp hybridized The

More information

Chapter 25 The Chemistry of Life: Organic Chemistry. 25.1 Some General Characteristics of Organic Molecules

Chapter 25 The Chemistry of Life: Organic Chemistry. 25.1 Some General Characteristics of Organic Molecules Chapter 25 The Chemistry of Life: Organic Chemistry general characteristics of organic molecules introduction to hydrocarbons alkanes unsaturated hydrocarbons functional groups: alcohols and ethers compounds

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

Figure 8. Example of simple benzene naming with chlorine and NO 2 as substituents.

Figure 8. Example of simple benzene naming with chlorine and NO 2 as substituents. BENZENE NAMING EXPLAINED. This was excerpted from CHEM WIKI and is used with appreciation to the authors. http://chemwiki.ucdavis.edu/organic_chemistry/hydrocarbons/aromatics/naming_the_benzenes. Simple

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

13.1 Alcohols and Phenols. Nomenclature. Nomenclature. Nomenclature. Alcohols possess a hydroxyl group ( OH). Hydroxyl groups in natural compounds.

13.1 Alcohols and Phenols. Nomenclature. Nomenclature. Nomenclature. Alcohols possess a hydroxyl group ( OH). Hydroxyl groups in natural compounds. 13.1 Alcohols and Phenols Alcohols possess a hydroxyl group ( OH). 13.1 Alcohols and Phenols Hydroxyl groups in natural compounds. Hydroxyl groups are extremely common in natural compounds. 13-1 13-2 13.1

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

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

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

Organic Chemistry II / CHEM 252 Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group

Organic Chemistry II / CHEM 252 Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group Organic Chemistry II / CHEM 252 Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group Bela Torok Department of Chemistry University of Massachusetts Boston Boston, MA 1 Nomenclature

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

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

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

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

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

Unit VII Compound Formula Writing and Nomenclature Review Sheet. Chapter 6: Basic Naming & Formula Writing

Unit VII Compound Formula Writing and Nomenclature Review Sheet. Chapter 6: Basic Naming & Formula Writing Unit VII Compound Formula Writing and Nomenclature Review Sheet Chapter 6: Basic Naming & Formula Writing 1. Distinguish among: a. Atoms b. Molecules: combinations of covalently bonded nonmetals c. Formula

More information

Chapter 7 - Alkenes and Alkynes I

Chapter 7 - Alkenes and Alkynes I Andrew Rosen Chapter 7 - Alkenes and Alkynes I 7.1 - Introduction - The simplest member of the alkenes has the common name of ethylene while the simplest member of the alkyne family has the common name

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

Chemical Tests for Alkanes, Alkenes, and Aromatic Compounds

Chemical Tests for Alkanes, Alkenes, and Aromatic Compounds Chemical Tests for Alkanes, Alkenes, and Aromatic Compounds Introduction There are four types of hydrocarbons: alkanes, alkenes, alkynes, and aromatic compounds, each type with different chemical properties.

More information

NMR Spectroscopy of Aromatic Compounds (#1e)

NMR Spectroscopy of Aromatic Compounds (#1e) NMR Spectroscopy of Aromatic Compounds (#1e) 1 H NMR Spectroscopy of Aromatic Compounds Erich Hückel s study of aromaticity in the 1930s produced a set of rules for determining whether a compound is aromatic.

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 10 Introduction to Organic Chemistry: Alkanes. Organic Chemistry. 10.1 Organic Compounds. Organic vs. Inorganic.

Chapter 10 Introduction to Organic Chemistry: Alkanes. Organic Chemistry. 10.1 Organic Compounds. Organic vs. Inorganic. Chapter 10 Introduction to Organic Chemistry: Alkanes 10.1 Organic Compounds Organic Chemistry An organic compound is a compound made from carbon atoms. has one or more C atoms. has many H atoms. may also

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

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

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

Unit Vocabulary: o Organic Acid o Alcohol. o Ester o Ether. o Amine o Aldehyde

Unit Vocabulary: o Organic Acid o Alcohol. o Ester o Ether. o Amine o Aldehyde Unit Vocabulary: Addition rxn Esterification Polymer Alcohol Ether Polymerization Aldehyde Fermentation Primary Alkane Functional group Saponification Alkene Halide (halocarbon) Saturated hydrocarbon Alkyne

More information

Homework Chapter 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions mandatory problems are highlighted (up to page 16)

Homework Chapter 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions mandatory problems are highlighted (up to page 16) Homework Chapter 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions mandatory problems are highlighted (up to page 16) SHORT ANSWER IUPAC Naming Instructions: Provide proper IUPAC

More information

ALKENES, ALKYNES and AROMATIC COMPOUNDS Chapter 13

ALKENES, ALKYNES and AROMATIC COMPOUNDS Chapter 13 ALKENES, ALKYNES and AROMATIC COMPOUNDS Chapter 13 13.1 Introduction An ALKENE is a hydrocarbon with a double C bond that looks like C=C An ALKYNE is a hydrocarbon with a triple C bond that looks like

More information

Identification of Unknown Organic Compounds

Identification of Unknown Organic Compounds Identification of Unknown Organic Compounds Introduction The identification and characterization of the structures of unknown substances are an important part of organic chemistry. Although it is often

More information

Chapter 4 Introduction to Organic Compounds

Chapter 4 Introduction to Organic Compounds Chapter 4 Introduction to Organic Compounds Outline 4.1 Alkanes: The Simplest Organic Compounds 4.2 Representing Structures of Organic Compounds 4.3 Families of Compounds Functional Groups 4.4 Nomenclature

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

the double or triple bond. If the multiple bond is CH 3 C CCHCCH 3

the double or triple bond. If the multiple bond is CH 3 C CCHCCH 3 Alkenes, Alkynes, and Aromatic ompounds Alkenes and Alkynes Unsaturated contain carbon-carbon double and triple bond to which more hydrogen atoms can be added. Alkenes: carbon-carbon double bonds Alkynes:

More information

Nomenclature of organic compounds

Nomenclature of organic compounds P.1 Nomenclature of organic compounds A. Alkanes (C n H 2n+2 ) i. The following table give the names of some root names different number of carbon atoms of hydrocarbon. CH 4 methane C 6 H 14 hexane C 2

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

Monday, September 10th

Monday, September 10th Monday, September 10th Review Chapter 11 iclicker Quiz #1 Chapter 12 Chapter 13(maybe) Group assignment Keep checking the class webpage at www.bhsu.edu/danasunskis. Go to the course tab then CHEM107 Lecture

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

Alkenes and Alkynes. Chapter 1.2

Alkenes and Alkynes. Chapter 1.2 Alkenes and Alkynes Chapter 1.2 Unsaturated Hydrocarbons Alkenes and alkynes are unsaturated hydrocarbons An alkene is a hydrocarbon that contains at least one carbon-carbon double bond An alkyne is a

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

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

Chapter 11 Unsaturated Hydrocarbons Alkenes and Alkynes

Chapter 11 Unsaturated Hydrocarbons Alkenes and Alkynes 1 Chapter 11 Unsaturated ydrocarbons Alkenes and Alkynes Saturated ydrocarbons 2 Saturated hydrocarbons have the maximum number of hydrogen atoms attached to each carbon atom are alkanes and cycloalkanes

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

IDENTIFYING STUDENTS MISCONCEPTIONS IN A-LEVEL ORGANIC CHEMISTRY

IDENTIFYING STUDENTS MISCONCEPTIONS IN A-LEVEL ORGANIC CHEMISTRY IDENTIFYING STUDENTS MISCONCEPTIONS IN A-LEVEL ORGANIC CHEMISTRY Lim Choon Huat Bryan Innova Junior College Abstract In recent years, research in science education has been focused on identifying and addressing

More information

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. CHM 210 Chemistry Homework #6 Alkanes (Ch. 10) Due: MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Compounds that have the same molecular formula

More information

Alkenes: Alkynes: Example: What are all the structural possibilities for C 3 H 4? Unsaturated hydrocarbons: Bonding Patterns of Multiple Bonds

Alkenes: Alkynes: Example: What are all the structural possibilities for C 3 H 4? Unsaturated hydrocarbons: Bonding Patterns of Multiple Bonds Chapter 3 Organic Chem: Alkenes & Alkynes Don t need to know the following reactions found on summary pages 110-112: 1. Hydroboration-Oxidation 2. Cycloaddition to Conjugated Dienes 3. Alkyne reaction

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 18 Organic Chemistry I: The Hydrocarbons

Chapter 18 Organic Chemistry I: The Hydrocarbons Key oncepts Overview hapter 18 Organic hemistry I: The ydrocarbons Aliphatic ydrocarbons (Sections 18.1 18.7) hydrocarbons, types of hydrocarbons, aliphatic hydrocarbon, aromatic hydrocarbon, condensed

More information

Chapter 10 Introduction to Organic Chemistry: Alkanes. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition

Chapter 10 Introduction to Organic Chemistry: Alkanes. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition 1 hapter 10 Introduction to Organic hemistry: Alkanes Organic hemistry and Organic ompounds 2 An organic compound is a compound made from carbon atoms has one or more atoms has many atoms may also contain

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

Alkanes. Chapter 1.1

Alkanes. Chapter 1.1 Alkanes Chapter 1.1 Organic Chemistry The study of carbon-containing compounds and their properties What s so special about carbon? Carbon has 4 bonding electrons. Thus, it can form 4 strong covalent bonds

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

Acid-Base Chemistry of Sugars

Acid-Base Chemistry of Sugars Acid-Base Chemistry of Sugars Lewis acids are electron pair acceptors while Lewis bases are electron pair donors. Last time we saw that sugar molecules have a carbonyl carbon that acts as a Lewis acid

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

1 Lecture 5 Resonance 1. Lone pair next to empty 2p orbital

1 Lecture 5 Resonance 1. Lone pair next to empty 2p orbital 1 Lecture 5 esonance 1. Lone pair next to empty 2p orbital sp 2 + is more common sp + is less common + needs electrons, has to overlap with a. an adjacent 2p lone pair with electrons b. an adjacent pi

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

IDENTIFICATION OF ALCOHOLS

IDENTIFICATION OF ALCOHOLS IDENTIFICATION OF ALCOHOLS Alcohols are organic compounds that which considered as derivatives of water. One of the hydrogen atoms of water molecule (H-O-H) has been replaced by an alkyl or substituted

More information

3/9/2012. First Ten Alkanes. Simple Organic Chemistry Basic Structure and Nomenclature. (Nomenclature) Rules for Naming Alkanes.

3/9/2012. First Ten Alkanes. Simple Organic Chemistry Basic Structure and Nomenclature. (Nomenclature) Rules for Naming Alkanes. C Simple Organic Chemistry Basic Structure and Nomenclature First Ten Alkanes Formula Name Formula Name CH4 Methane C6H14 Hexane C2H5 Ethane C7H16 Heptane C3H8 Propane C8H18 Octane C4H10 Butane C9H20 Nonane

More information

Chapter 5 Classification of Organic Compounds by Solubility

Chapter 5 Classification of Organic Compounds by Solubility Chapter 5 Classification of Organic Compounds by Solubility Deductions based upon interpretation of simple solubility tests can be extremely useful in organic structure determination. Both solubility and

More information

EXPERIMENT 3 (Organic Chemistry II) Nitration of Aromatic Compounds: Preparation of methyl-m-nitrobenzoate

EXPERIMENT 3 (Organic Chemistry II) Nitration of Aromatic Compounds: Preparation of methyl-m-nitrobenzoate EXPERIMENT 3 (Organic Chemistry II) Nitration of Aromatic Compounds: Preparation of methyl-m-nitrobenzoate Pahlavan/Cherif Purpose a) Study electrophilic aromatic substitution reaction (EAS) b) Study regioselectivity

More information

(Woods) Chem-131 Lec-15 09-4 Carboxyllic acid 1. Carboxylic Acid Derivatives Esters, Acid Anhydrides, Amides, and Acid Halides

(Woods) Chem-131 Lec-15 09-4 Carboxyllic acid 1. Carboxylic Acid Derivatives Esters, Acid Anhydrides, Amides, and Acid Halides (Woods) Chem-131 Lec-15 09-4 Carboxyllic acid 1 Carboxylic Acid Derivatives Esters, Acid Anhydrides, Amides, and Acid Halides The oxidation state of carbon in a carboxylic acid is the highest of the organic

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

Substituted Alkanes. Alcohol Amine Ether Thiol

Substituted Alkanes. Alcohol Amine Ether Thiol Substituted Alkanes While alkanes have very few reactions that occur, combustion and some radical reactions, substituted alkanes display a variety of reactions and properties X ften the amount of information

More information

IUPAC System of Nomenclature

IUPAC System of Nomenclature IUPAC System of Nomenclature The IUPAC (International Union of Pure and Applied Chemistry) is composed of chemists representing the national chemical societies of several countries. ne committee of the

More information

Copyright 2010 Pearson Education, Inc. Chapter Fourteen 1

Copyright 2010 Pearson Education, Inc. Chapter Fourteen 1 An alcohol has an OH bonded to an alkyl group; a phenol has an OH bonded directly to an aromatic ring; and an ether has an O bonded to two organic groups. Chapter Fourteen 1 Ethyl alcohol, dimethyl ether,

More information

Laboratory 22: Properties of Alcohols

Laboratory 22: Properties of Alcohols Introduction Alcohols represent and important class of organic molecules. In this experiment you will study the physical and chemical properties of alcohols. Solubility in water, and organic solvents,

More information

Ch 12. Alkanes Introduction to Organic Chemistry: Simple Hydrocarbons

Ch 12. Alkanes Introduction to Organic Chemistry: Simple Hydrocarbons Ch 12. Alkanes Introduction to Organic Chemistry: Simple Hydrocarbons Diagram of Methane. Member of Alkane family of hydrocarbons. Alkanes have only single bonds. When carbon is bonded to four atoms, the

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

14 Friedel-Crafts Alkylation

14 Friedel-Crafts Alkylation 14 Friedel-Crafts Alkylation 14.1 Introduction Friedel-Crafts alkylation and acylation reactions are a special class of electrophilic aromatic substitution (EAS) reactions in which the electrophile is

More information

Synthesis of Isopentyl Acetate

Synthesis of Isopentyl Acetate Experiment 8 Synthesis of Isopentyl Acetate Objectives To prepare isopentyl acetate from isopentyl alcohol and acetic acid by the Fischer esterification reaction. Introduction Esters are derivatives of

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

CHM220 Addition lab. Experiment: Reactions of alkanes, alkenes, and cycloalkenes*

CHM220 Addition lab. Experiment: Reactions of alkanes, alkenes, and cycloalkenes* CM220 Addition lab Experiment: Reactions of alkanes, alkenes, and cycloalkenes* Purpose: To investigate the physical properties, solubility, and density of some hydrocarbon. To compare the chemical reactivity

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

13C NMR Spectroscopy

13C NMR Spectroscopy 13 C NMR Spectroscopy Introduction Nuclear magnetic resonance spectroscopy (NMR) is the most powerful tool available for structural determination. A nucleus with an odd number of protons, an odd number

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

Organic Chemistry. Hydrocarbons. Introduction to Organic Molecules. The simplest organic molecules containing only carbon and hydrogen atoms

Organic Chemistry. Hydrocarbons. Introduction to Organic Molecules. The simplest organic molecules containing only carbon and hydrogen atoms Introduction to Organic Molecules Organic Chemistry: (1828) Friedrich Wohler first synthesized an organic compound from an inorganic source leading to the birth of Organic Chemistry. Organic chemistry

More information

1) A compound gives a mass spectrum with peaks at m/z = 77 (40%), 112 (100%), 114 (33%), and essentially no other peaks. Identify the compound.

1) A compound gives a mass spectrum with peaks at m/z = 77 (40%), 112 (100%), 114 (33%), and essentially no other peaks. Identify the compound. 1) A compound gives a mass spectrum with peaks at m/z = 77 (40%), 112 (100%), 114 (33%), and essentially no other peaks. Identify the compound. First, your molecular ion peak is 112 and you have a M+2

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

Mr. Kent s Organic Chemistry Unit Notes I Basic Concepts

Mr. Kent s Organic Chemistry Unit Notes I Basic Concepts Mr. Kent s Organic Chemistry Unit Notes I Basic Concepts A. Organic Chemistry-The study of containing compounds. 1. They occur extensively in nature because all living things are made of containing compounds.

More information

How to Quickly Solve Spectrometry Problems

How to Quickly Solve Spectrometry Problems How to Quickly Solve Spectrometry Problems You should be looking for: Mass Spectrometry (MS) Chemical Formula DBE Infrared Spectroscopy (IR) Important Functional Groups o Alcohol O-H o Carboxylic Acid

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

CHEM 203 Exam 1. KEY Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question.

CHEM 203 Exam 1. KEY Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question. CHEM 203 Exam 1 KEY Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question. _D C 1. Which of the following elements is a large percentage of both

More information