Chapter 12 Electrophilic and Nucleophilic Aromatic Substitution
|
|
|
- Griffin Geoffrey Fields
- 7 years ago
- Views:
Transcription
1 Chapter 12 Electrophilic and Nucleophilic Aromatic Substitution
2 CHAPTER 12 Electrophilic and Nucleophilic Aromatic Substitution Aromatic compounds may undergo substitution reactions. Electrophilic aromatic substitutions (S E Ar, or sometimes EAS) are the central focus and these reactions are treated in the first 18 sections. Nucleophilic aromatic substitutions (S N Ar, or sometimes NAS) are treated in the last 3 sections. S E Ar reactions involve the substitution of a hydrogen atom on an aromatic ring. The reactions are initiated by a very reactive electronphile. The S E Ar mechanism is discussed in detail and can be used to explain regiochemistry of the reaction on substituted aromatic systems. S N Ar reactions differ from S E Ar in that these reactions involve the substitution of a leaving group. The S N Ar mechanism shares many similarities with S E Ar and, a familiarity with the S E Ar will help understanding the the S N Ar mechanism. These mechanisms involves a heavy does of resonance, so please review this topic from chapter 1. Chapter 12 Problems: 33, 34, 39, 40, 46, 49, 50, 53, 57, 59 Chapter 12-2
3 PREVIEW OF ELECTROPHILIC AND NUCLEOPHILIC AROMATIC SUBSTITUTIONS S E Ar is mechanistically related to previously presented electrophilic addition (chapter 6). Likewise, S N Ar is related to nucleophilic (aliphatic) substitution (chapters 4 and 8). Chapter 12-3
4 FIVE S E Ar REACTIONS 1. Nitration 2. Sulfonation 3. Halogenation 4. Friedel-Crafts Alkylation 5. Friedel-Crafts Acylation Chapter 12-4
5 GENERAL MECHANISM FOR S E Ar Two-step mechanism that begins with an electrophile removing electrons from an aromatic π bond, followed by a base removing a hydrogen to reform the alkene (aromaticity). Chapter 12-5
6 NITRATION OF BENZENE Overall reaction replaces a aromatic hydrogen with a nitro group (-NO 2 ) Requires the formation of the nitronium ion (NO 2+ ), a very good electrophile. Chapter 12-6
7 SULFONATION OF BENZENE Overall reaction replaces a aromatic hydrogen with a sulfonic acid group (-SO 3 H). Sulfur trioxide is suspected to be the reacting electrophile (SO 3 ). Chapter 12-7
8 HALOGENATION OF BENZENE Overall reaction replaces a aromatic hydrogen with a halide (-X), X = Br, Cl, I. Dihalogens are not electrophilic enough to react on their own, so an reactive species with an electron deficient halogen must be created. Chapter 12-8
9 FRIEDEL-CRAFTS ALKYLATION OF BENZENE Overall reaction replaces a aromatic hydrogen an alkyl group (-R). The reactive electrophile is a carbocation generated from an alkyl halide and a strong Lewis acid. Chapter 12-9
10 FRIEDEL-CRAFTS ALKYLATION OF BENZENE (cont.) Because the reactive electrophile is a carbocation, reactions will only work with 3 and 2 cations. Possible carbocation rearrangements may occur. Chapter 12-10
11 FRIEDEL-CRAFTS ACYLATION OF BENZENE Overall reaction replaces a aromatic hydrogen an acyl group (-COR). The reactive electrophile is an acylium ion which is generated with an acid halide and a strong Lewis acid. Chapter 12-11
12 REDUCTION OF ARYL KETONES TO METHYLENES Reduction of an aromatic acyl group leads to a (-CH 2 -); equivalent to an alkylation with a 1 carbocation. Chapter 12-12
13 REDUCTION OF ARYL KETONES TO METHYLENES Clemmensen reduction under acidic conditions. Wolff-Kishner reduction under basic condition. Chapter 12-13
14 REACTION RATES OF S E Ar Activating groups will increase S E Ar rates. Deactivating groups will decrease S E Ar rates. Chapter 12-14
15 REGIOSELECTIVITY IN S E Ar: EXAMPLE TOLUENE A methyl group directs the reaction to the ortho and para positions. ortho nitration meta nitration para nitration Chapter 12-15
16 REGIOSELECTIVITY IN S E Ar: EXAMPLE (TRIFLUOROMETYL)BENZENE A trifluoro-methyl group directs the reaction to the meta positions. ortho nitration meta nitration para nitration Chapter 12-16
17 REGIOSELECTIVITY IN S E Ar: EXAMPLE (TRIFLUOROMETYL)BENZENE Hammond s postulate is invoked to explain regiochemistry. Chapter 12-17
18 CLASSIFICATION OF SUBSTITUENTS Chapter 12-18
19 SUBSTITUENT EFFECT: ACTIVATING GROUPS Activating groups (aka electron donating groups or EDG) increase the overall reaction rate and direct ortho/para. Chapter 12-19
20 SUBSTITUENT EFFECT: DEACTIVATING GROUPS Deactivating groups (aka electron withdrawing groups or EWG) decrease the overall reaction rate and direct meta. Chapter 12-20
21 SUBSTITUENT EFFECT: HALOGENS Halogens are exceptions. They are decrease the reaction rate, but direct otho/para. Chapter 12-21
22 MULTIPLE SUBSTITUENTS Case 1: groups can reinforce each other. Chapter 12-22
23 MULTIPLE SUBSTITUENTS Case 2: sterics may also direct substitution. Also, groups work against each other; stronger activator wins. Chapter 12-23
24 RETROSYNTHETIC ANALYSIS For multiple substituted benzenes, be sure to order the reactions correctly. Chapter 12-24
25 RETROSYNTHETIC ANALYSIS Don t forget about Friedel-Crafts acylation combined with reductions. Chapter 12-25
26 S E Ar ON OTHER ARENES Regiochemistry determined by electrophilic addition generates the more stable σ- complexes. For naphthalene, resonance forms with aromaticity will increase stability over resonance forms without aromaticity. Chapter 12-26
27 S E Ar ON HETEROCYCLIC AROMATIC COMPOUNDS Regiochemistry determined by electrophilic addition generates the more stable σ- complexes. Chapter 12-27
28 NUCLEOPHILIC AROMATIC SUBSTITUTION: S N Ar Aryl halides can undergo nucleophilic substitution. Nitro groups ( NO 2 ) at the ortho or para positions to the halide ACTIVATE the reaction (unlike S E Ar reactions). Chapter 12-28
29 S N Ar MECHANISM: ADDITION-ELIMINATION Nucleophilic addition to the aryl ring produces a cyclohexadienyl anion. Nitro groups next to a carbanion have an additional resonance form. Dissociation of the leaving group regenerates aromaticity in the ring. Chapter 12-29
30 OTHER EXAMPLES OF S N Ar Hexafluorobenzene is susceptible to S N Ar. Heterocyclic compound with specifically placed electronegative atoms can also help stabilize anionic intermediates. Chapter 12-30
31 S N Ar MECHANISM: BENZYNE INTERMEDIATES* Halobenzene under stongly basic conditions can eliminate to produce a cyclic alkyne, called a benzyne. Nucleophilic attack of benzyne, followed by protonation of the carbanion completes the substitution product. * In Descriptive Passage section at the end of chapter 12 on pp Chapter 12-31
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
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
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.
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,
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
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
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
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
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
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,
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
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
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).
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
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
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
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
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.
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
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
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
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
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
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
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:
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:
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
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
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
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
Typical Infrared Absorption Frequencies. Functional Class Range (nm) Intensity Assignment Range (nm) Intensity Assignment
Typical Infrared Absorption Frequencies Functional Class Range (nm) Intensity Assignment Range (nm) Intensity Assignment Alkanes 2850-3000 CH 3, CH 2 & CH 2 or 3 bands Alkenes 3020-3100 1630-1680 1900-2000
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
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
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.
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
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 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
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
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
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
CHE 232 - Organic Chemistry Exam 1, February 10, 2004
CE 232 - rganic Chemistry Exam 1, February 10, 2004 ame Student ID o. Before you begin this exam: First: You are allowed to have a simple model set at your seat. Please put away all other materials. Second:
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.
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,
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
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
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,
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,
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.
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
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,
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
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.
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
Physicochemical Properties of Drugs
Therapeutics I Michael B. Bolger 1/3/02 bjectives: At the end of the next hour: Physicochemical Properties of Drugs 1. The student should be able to calculate the degree of ionization for an acidic or
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
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
Organometallics Study Seminar Chapter 13: Metal-Ligand Multiple Bonds
Organometallics Study Seminar Chapter 13: Metal-Ligand Multiple Bonds Contents 1. Carbene Complexes 2. Silylene Complexes 3. Metal-Heteroatom Multiple Bonds 1. Carbene Complexes 1.1 Classes of Carbene
INTERMOLECULAR FORCES
INTERMOLECULAR FORCES Intermolecular forces- forces of attraction and repulsion between molecules that hold molecules, ions, and atoms together. Intramolecular - forces of chemical bonds within a molecule
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
1. Oxidation number is 0 for atoms in an element. 3. In compounds, alkalis have oxidation number +1; alkaline earths have oxidation number +2.
à xidation numbers In the Lewis model of bonding, when nonidentical atoms are bonded together, an important consideration is how the bonding electrons are apportioned between the atoms. There are two different
Chapter 14 - Acids and Bases
Chapter 14 - Acids and Bases 14.1 The Nature of Acids and Bases A. Arrhenius Model 1. Acids produce hydrogen ions in aqueous solutions 2. Bases produce hydroxide ions in aqueous solutions B. Bronsted-Lowry
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
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
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
Ch 13_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) In organic chemistry, the term unsaturated means a molecule A) which contains one or more
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
ACID and BASES - a Summary
AID and BASES - a Summary Stefan Svensson 2004 Brönsted-Lowry : Acids donate protons Lewis -acid : Electron pair acceptor Bases accept protons Lewis-base: Electron pair donator. Acetic acid ättiksyra 3
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
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:
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
ORGANIC CHEM I Practice Questions for Ch. 4
ORGANIC CHEM I Practice Questions for Ch. 4 1) Write an equation to describe the initiation step in the chlorination of methane. 2) Reaction intermediates that have unpaired electrons are called. 3) When
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
Self Assessment_Ochem I
UTID: 2013 Objective Test Section Identify the choice that best completes the statement or answers the question. There is only one correct answer; please carefully bubble your choice on the scantron sheet.
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
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
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
Chapter 2 Polar Covalent Bonds: Acids and Bases
John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 2 Polar Covalent Bonds: Acids and Bases Modified by Dr. Daniela R. Radu Why This Chapter? Description of basic ways chemists account for chemical
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
Theme 3: Bonding and Molecular Structure. (Chapter 8)
Theme 3: Bonding and Molecular Structure. (Chapter 8) End of Chapter questions: 5, 7, 9, 12, 15, 18, 23, 27, 28, 32, 33, 39, 43, 46, 67, 77 Chemical reaction valence electrons of atoms rearranged (lost,
MOLECULAR REPRESENTATIONS AND INFRARED SPECTROSCOPY
MLEULAR REPRESENTATINS AND INFRARED SPETRSPY A STUDENT SULD BE ABLE T: 1. Given a Lewis (dash or dot), condensed, bond-line, or wedge formula of a compound draw the other representations. 2. Give examples
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
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
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
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
Brønsted-Lowry Acids and Bases
Brønsted-Lowry Acids and Bases 1 According to Brønsted and Lowry, an acid-base reaction is defined in terms of a proton transfer. By this definition, the reaction of Cl in water is: Cl(aq) + Cl (aq) +
11.4 NUCLEOPHILIC SUBSTITUTION REACTIONS OF EPOXIDES
.4 NUEPII SUBSTITUTIN REATINS F EPXIDES 495 (d When tert-butyl methyl ether is heated with sulfuric acid, methanol and -methylpropene distill from the solution. (e Tert-butyl methyl ether cleaves much
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
H 2O gas: molecules are very far apart
Non-Covalent Molecular Forces 2/27/06 3/1/06 How does this reaction occur: H 2 O (liquid) H 2 O (gas)? Add energy H 2O gas: molecules are very far apart H 2O liquid: bonding between molecules Use heat
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
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
NOMENCLATURE OF ORGANIC COMPOUNDS 2010, 2003, 1980, by David A. Katz. All rights reserved.
NMENCLATURE F RGANIC CMPUNDS 2010, 2003, 1980, by David A. Katz. All rights reserved. rganic chemistry is the chemistry of carbon compounds. Carbon has the ability to bond with itself to form long chains
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
The strength of the interaction
The strength of the interaction Host Guest Supramolecule (host-guest complex) When is the host capable to recognize the guest? How do we define selectivity Which element will we use to design the host
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
For example: (Example is from page 50 of the Thinkbook)
SOLVING COMBINED SPECTROSCOPY PROBLEMS: Lecture Supplement: page 50-53 in Thinkbook CFQ s and PP s: page 216 241 in Thinkbook Introduction: The structure of an unknown molecule can be determined using
Organic Chemistry, 5e (Bruice) Chapter 17: Carbonyl Compounds II
Organic Chemistry, 5e (Bruice) Chapter 17: Carbonyl Compounds II 1) Which of the following compounds is an aldehyde? A) I B) II C) III D) IV E) V D Section: 17-1 2) Which of the following compounds is
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
Quantifying Nucleophilicity and Electrophilicity: The Mayr Scales. log k = s(n + E)
Quantifying ucleophilicity and Electrophilicity: The Mayr Scales E k E R R log k = s( + E) Valerie Shurtleff MacMillan Group Meeting July 10, 2013 A Brief History of Polar Reactivity Scales 1920s: G..
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
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,
Reactions of Aldehydes and Ketones
Reactions of Aldehydes and Ketones Structure Deduction using lassification Tests 1 Determination of Structure Determining the structure of an unknown organic compound is an exercise in deductive reasoning.
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