Amines (McM chapt 24)
|
|
- Gillian Doreen Hart
- 5 years ago
- Views:
Transcription
1 Amines (McM chapt 24) (: alkyl, aryl) - 2 Primary amine ' Secondary amine '' ' Tertiary amine ' ''' '' Quartenary ammonium salts Basic compounds ' '' - ' '' + pka Alkylamines: ca 9-11 Arylamines: ca 4-5 (anilines) (:, alkyl, aryl)
2 Synthesis Known react. from KJM10xx Alkylation (ammonia or amine, phtalimide) (:, alkyl, aryl) - Base - - Base - C 2 C Acidity c.f. 1,3-dicarbonyls eductive amination - 2 [red] Aldehyde ketone ammonia prim amine Imine 2 / i acb 3 etc sec amine - 2 [red] Iminium ion
3 eductions itriles Azides Amides C itrile C LiAl 4 C Azide LiAl 4 C '' ' LiAl 4 Amide, ', '':, alkyl, aryl C '' ' 3 - Aromatic nitro compounds Ar- 2 [red] Ar- 2 ed: 2 / cat SnCl 2, +
4 Synthesis: ew reactions ofmann rearrangement a, Br prim amide C 2 2 Br-Br Br Br C Isocyanate 2 Br Br Acid / base properties amides 2 + pka ca C pka ca -0.5 carbamic acid instable 3 o resonance stab.
5 Curtius rearrangement C 2 3 2, heat + 2 acyl azide acyl azide Cl acyl halide 3 C Isocyanate 2 - C 2-2 Mechanistic. related to ofmann rearrang. 2 Br C Isocyanate 2 - C 2-2 Br
6 eactions of amines (Alkylamines) Alkylamines: Alkylation Acylation / synth of amide ofmann elimination ( ofmann rearrangement) E2 elimination to form alkene E2: mechanism B ' ' ' ' + B + = halogen, () 2 Strong base / bad leaving group C 3 I (excess) Base 2
7 2 C 3 I (excess) Base emoval of less sterically hindered ot necessarily most stable alkene formed 2 C 3 I (excess) 3 C C 3 C3 I Ag C C 3 C3 AgI + 3 C C3 C 3 Much better leaving group than 2 Morphine C 3 Base C 3 3 C C 3 Ph 3 C C 3 Codeine 3 C C 3 -I pka=10.0 pka ca 17 C 3 C 3 -I I C 2 C 3 offman elim C 3 C3 3 C 3 C 3 C
8 eactions of Arylamines (aniline derivatives) 2 Aniline Weak base (pka ca 4.6) ighly Activated for E-fil Ar Subst (o/p) Protect. as amide: Less activated, still o/p ' 3 o/p directing m-directing ucleophilic Aromatic Substitution - Mechanisms S Ar u u u u u S 1 Benzyne S1: Involves radicals (VS: Vicarious ucl. Subst.)
9 Formation of Diazonium Salts and the Sandmeyer eaction ' ' Diazonium salt Diazo compound Azide S 4 / Synthetically seldom useful prim alkylamine very unstable u 2 u Substitution 2 S 4 / 2 Y Aryl amine elatively stable Diazo couplng Y Y:, 2
10 Diazotation of primary amine 2 nitrous acid (salpetersyrling) dinitrogen trioxide + 2 Ar 2 Ar Ar itrosoamine taut Ar Sec amine gives nitroso compound Ar + 2 Ar Ar itrosoamine Amines with acidic a- may give diazo compounds ' 2 C 2 2 C ' - 2 C
11 Toxicity nitroso compounds (not in McM) - Alkylation of biomolecules 2 / 3 endoplasmatic reticulum 3 C 3 C CYP450 enzyme 3 C C C 3 C 3 C sec alkylamine C 3 3 C 3 C C 3 S 2 C 3-7 alkylation of guanine in DA S-methylated cysteine in a peptide/protein
12 I C CuC ai or KI Br + / 2 or CuBr CuCl Cl 2 as leaving group Cu 2 / Cu( 3 ) 2 2 BF 4 3 P 4 F S1 like mechanism or radical mechanism u u Cu - 2 Cu 2+ Cu + Cu-salt mediated react. Sandmeyer react. (radical mech.)
13 Diazo coupling Y Phenol Aniline der (eactive u) + Electrophile Electrophilic Aromatic subst. Y Base Y Azo dyes Bayer etc Late 1800-century, ex. 3 S Metylorange 2 Pararødt Metylorange 3 S 3 S p < 3.1 p >4.4
14 Azo dyes Bayer etc Late 1800-century, ex. 3 S Metylorange Screening of dyes as antibacterials 2 Pararødt 1932: Prontocil active against Streptoccocces infection no activity on bacterial cultures 2 S : Prontocil metabilized (azoreductase) to Sulfanilamid in vivo 2 S 2 (rel. toxisk) Antibacterial sulfonamides Modern sulfa drugsr S 2 : Aryl or hetroaryl
15 eterocycles (McM chapt 24) Monocyclic or fused rings Cont. one ore more ring atom C (normally ; ; S) Aromatic, partly saturated or saturated ring(s) 5-Membered rings (eteroatom,, S) S Thiophene Pyrrole Thiophene ther examples Imidazole S Thiazole Indole 2 Adenine (purine der.) 2 =C 2 : istidine =: istamine 3 C S 2 Thiamin (Vit B1) C 3 '' = '= '''= ' = '=C 2 '''= Serotonin =Ac '= '''=C 3 Tryptophane Melatonin
16 Criteria for Aromaticity (ückel) (Monocyclic) ring Planar o of π-electrons in conjugation 4n+2 (n: 0, 1, 2,...) Cyclopentadienyl anion S S Thiophene : S, Se e - in d-orb.
17 Benzene 6 π electrons Energy Cyclobutadiene 4 π electrons Diradical Cyclopentadienyl anion 6 π electrons Thiophene 6 π electrons S All π electrons in the bonding M
18 5-membered rings - electron rich on C - reactive i E-fil. Ar subst. : S, Se e - in d-orb. + E E E E E + E E E E eact. in α-position generally preferred Selectivity not always good eact.: Pyrrole > thiophene > furan
19 6-Membered rings (eteroatom ) Pyridine ther examples Quinoline Pyrimidine Pyrazine Pyridazine are in nature 3 C Quinine 2 Cytosine Ant pheremone 2 ydralazine Antihypertensive drug
20 Pyridine as a base + pka: 5.2 sp 2 less basic than sp 3 S pka 0.4 pka 11.3 pka 7.1 ( amidine) pka 2.5
21 Electrophilic eaction on Carbon: E-phil. Ar. Subs. 6-membered rings - electron deficient on C - reactivity + E E E E + res. forms Both C and may react 3/5 pos. most reactive C Diazines less reactive Sulfonation, itration, halogenatil ot FC react.
22 ucleophilic Aromatic Substitution S Ar u u u u u S 1: Via arylic cation Benzyne S1: Involves radicals VS: Vicarious nucl. Subst. 6-membered rings - electron deficient - reactive in u-fil. Ar subst. Cl Me Me Cl Me + res. form 2 / 4 Pos. reactive; electron def. C, neg. charge partly on in intermed 3 / 5-Pos. much less reactive (benzenoid pos.)
Amines. Amines are organic compounds containing a nitrogen functionality. primary secondary tertiary quaternary
Amines Amines are organic compounds containing a nitrogen functionality Depending upon the number of alkyl, or aryl, groups attached to nitrogen determines its classification, or order 2 primary secondary
More informationChapter 22: Amines. Organic derivatives of ammonia, NH 3. Nitrogen atom have a lone pair of electrons, making the amine both basic and nucleophilic
hapter 22: Amines. rganic derivatives of ammonia, 3. itrogen atom have a lone pair of electrons, making the amine both basic and nucleophilic 22.1: Amines omenclature. (please read) sp 3 Amines are classified
More informationAlchohols, Phenols, Ethers
Aromatic ompounds Aromaticity lectrophilic aromatic subst. epetition cleophilic aromatic subst. (McM 7th ed, 16.7) Benzyne (McM 7th ed, 16.8) eduction of aromatics (McM 7th ed, 16.10) Alchohols, Phenols,
More informationLoudon Chapter 23 Review: Amines CHEM 3331, Jacquie Richardson, Fall Page 1
Loudon Chapter 23 eview: Amines CEM 3331, Jacquie ichardson, Fall 2010 - Page 1 This chapter is about the chemistry of nitrogen. We ve seen it before in several places, but now we can look at several reactions
More informationR N R N R N. primary secondary tertiary
Chapter 19 Amines omenclature o assification of amines Amines are classified as 1, 2, or 3 based on how many R groups are attached to the nitrogen R R R R R R primary secondary tertiary When there are
More informationAmines Amines (e.g. RNH 2 ) are organic derivatives of ammonia, NH 3 similar to ammonia
148Exam 2 notes rganic hemistry (e.g. 2 ) are organic derivatives of ammonia, 3 similar to ammonia omenclature: suffix 2 prefix 2 ( 3 ) 2 Types: Primary (1 o ), secondary (2 o ), tertiary (3 o ) or quaternary
More informationAmines. Chapter 24 Organic Chemistry, 8th Edition. John McMurry
Amines Chapter 24 Organic Chemistry, 8th Edition John McMurry 1 Introduction Amines are stronger bases and better nucleophiles than other neutral organic compounds. 2 Nomenclature 1 Amines are named using
More informationCHAPTER 22: Amines R 2 H N N N R 1. cadeverine N CH 3. nicotine
Based on notes by JZ updated 4/2018 Amines are Biologically Important CAPTE 22: Amines Amino acids are the basis of all peptides and proteins. These are the tissue building blocks and nature's catalysts
More information1. LiAlH4 :.. :.. 2. H3O +
Ch 24 Amines Description of Amines - An amine is a compound with a nitrogen atom that has single bonds to carbon and hydrogen atoms. - An uncharged nitrogen atom normally has three bonds and a lone pair.
More information2016 Pearson Education, Inc. Isolated and Conjugated Dienes
2016 Pearson Education, Inc. Isolated and Conjugated Dienes 2016 Pearson Education, Inc. Reactions of Isolated Dienes 2016 Pearson Education, Inc. The Mechanism Double Bonds can have Different Reactivities
More informationChapter 24. Amines. Based on McMurry s Organic Chemistry, 7 th edition
Chapter 24. Amines Based on McMurry s Organic Chemistry, 7 th edition Amines Organic Nitrogen Compounds Organic derivatives of ammonia, NH 3, Nitrogen atom with a lone pair of electrons, making amines
More informationLecture 13A 05/11/12. Amines. [Sn2; Hofmann elimination; reduction of alkyl azides, amides, nitriles, imines; reductive amination; Gabriel synthesis]
Lecture 13A 05/11/12 Amines [Sn2; ofmann elimination; reduction of alkyl azides, amides, nitriles, imines; reductive amination; Gabriel synthesis] Curtius and ofmann rearrangements Both of these, in principle,
More informationChapter 20 Amines-part 2
Reactions of Amines Lone pair on the nitrogen directs the chemistry of amines Chapter 20 Amines-part 2 The nitrogen lone pair can also make a carbon nucleophilic by resonance Amines can also activate carbons
More information896 Chapter 21 Amines H H N R R R N R H R N R H O H R 3 N CH 2 NH 2 NHCH 3
896 Chapter 21 Amines 21.20 Summary Section 21.1 Section 21.2 Section 21.3 Section 21.4 Alkylamines are compounds of the type shown, where R, R, and R are alkyl groups. ne or more of these groups is an
More information22.16 Nitrosation of Alkylamines
22.16 itrosation of Alkylamines itrite Ion, itrous Acid, and itrosyl Cation O O O O O O O O itrosyl Cation and itrosation O itrosyl Cation and itrosation O O itrosation of Secondary Alkylamines O O O nitrosation
More informationChemistry of Benzene: Electrophilic Aromatic Substitution
Chemistry of Benzene: Electrophilic Aromatic Substitution Why this Chapter? Continuation of coverage of aromatic compounds in preceding chapter focus shift to understanding reactions Examine relationship
More informationAlkylamines are compounds of the type shown, where R, R, and R are alkyl groups. One or more of these groups is an aryl group in arylamines.
22.20 Summary 955 22.20 SUMMARY Section 22.1 Alkylamines are compounds of the type shown, where R, R, and R are alkyl groups. ne or more of these groups is an aryl group in s. R R R R amine R Secondary
More informationChem 225 Notes Page 128. Chapter 23: Amines
Chem 225 Notes Page 128 Chapter 23: Amines I. Introduction A. Classification of Amines Amines are classified by the number of carbon groups attached to the nitrogen: ammonia primary (1 o ) secondary (2
More informationLoudon Chapter 23 Review: Amines Jacquie Richardson, CU Boulder Last updated 4/22/2018
This chapter is about the chemistry of nitrogen. We ve seen it before in several places, but now we can look at several reactions that are specific to nitrogen. Amines can be subdivided based on how many
More informationAmmonia Primary Secondary Tertiary Quarternary Ammonium Ion
1 Chapter 19: Amines I. Introduction: Classification: NH 3 RNH 2 R 2 NH R 3 N R 4 N + Ammonia Primary Secondary Tertiary Quarternary Ammonium Ion Amines are a very common functional group in organic chemistry,
More informationBenzene and Aromatic Compounds. Chapter 15 Organic Chemistry, 8 th Edition John McMurry
Benzene and Aromatic Compounds Chapter 15 Organic Chemistry, 8 th Edition John McMurry 1 Background Benzene (C 6 H 6 ) is the simplest aromatic hydrocarbon (or arene). Four degrees of unsaturation. It
More informationChapter 19: Amines. Introduction
Chapter 19: Amines Chap 19 HW: (be able to name amines); 37, 39, 41, 42, 44, 46, 47, 48, 53-55, 57, 58 Introduction Organic derivatives of ammonia. Many are biologically active. Chap 19: Amines Slide 19-2
More information20.5 Preparation of Amines
RGANIC CHEMISTRY 20.5 Preparation of Amines RGANIC CHEMISTRY 20.5A Through Nucleophilic Substitution Reactions Alkylation of Ammonia or Amines NaH NH 3 + R X RNH 3 X RNH2 R + R X R 2 X NaH R 2 NH R 2 NH
More informationDr. Munther Abdujaleel M.A. Assist. Prof. Org. Chem.
Dr. Munther Abdujaleel M.A. Assist. Prof. Org. Chem. Amines An amine, derivatives of ammonia NH 3 has the general formula RNH 2, R 2 NH, or R 3 N, where R is any alkyl or aryl group. For example: Adernalin
More informationLecture Notes Chemistry Mukund P. Sibi Lecture 36 Synthesis of Amines
Lecture otes hemistry 42-2008 Mukund P. Sibi Synthesis of Amines Amines can be prepared from a variety of starting materials. All of these methods involve functional group transformations. The main methods
More informationCH 24: Amines. Topics Synthesis of amines Hofmann Elimination Aryl amines Diazonium salts. Connections: CH 2 NH2. R Br R C N O NH 2 CH 3 N H 2 N + O -
rganic Chemistry otes by Jim Maxka C 24: Amines Topics Synthesis of amines ofmann Elimination Aryl amines Diazonium salts Connections: C C 2 2 2 C 2 2 2-3 - 2 2 2 C Ph- 2 Ph- Ph-C Ph- C24-1 rganic Chemistry
More informationReactions of Aromatic Compounds. Aromatic compounds do not react like other alkenes. With an appropriate catalyst, however, benzene will react
Reactions of Aromatic Compounds Aromatic compounds do not react like other alkenes 2 Fe 3 2 Does not form A major part of the problem for this reaction is the product has lost all aromatic stabilization,
More informationChapter 23 Amines Review of Concepts azide synthesis synthesis reductive amination sodium cyanoborohydride Hofmann elimination
Chapter 23 Amines eview of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 23. Each of the sentences below appears verbatim in the
More informationAROMATIC & HETEROCYCLIC CHEMISTRY
- 1 - AROMATIC & HETEROCYCLIC CHEMISTRY Aromatic Chemistry Aromaticity This confers an energetic stability over the equivalent double bond system. This can be explained from an MO point of view. The Huckel
More informationSp2002 Final Organic II 200pts (Weighted as 300) Good luck ( I believe in you, you can do it, etc.) and please read the questions!
Sp2002 Final rganic II 200pts (Weighted as 300) NAME: To not have your graded script placed outside my office please check this box Good luck ( I believe in you, you can do it, etc.) and please read the
More informationChapter 20. Amines. Nomenclature for amines. Aryl amines
Nomenclature for amines Chapter 20 Common names are widely used, named as alkylamines Systematic (IUPAC) nomenclature replaces the -e of the corresponding parent alkane with -amine Amines Simple secondary
More informationAmines and Heterocycles. McMurry: Chapter 24
Amines and Heterocycles McMurry: Chapter 24 Introduction to Amines and Heterocycles Amines and heterocycles (cyclic amines) are ammonia derivatives, many of whichare found widely in livingorganisms: 2
More informationAmines Reading Study Problems Key Concepts and Skills Lecture Topics: Amines: structure and nomenclature
Amines Reading: Wade chapter 19, sections 19-1-19-19 Study Problems: 19-37, 19-39, 19-40, 19-41, 19-44, 19-46, 19-47, 19-48, 19-51, 19-54 Key Concepts and Skills: Explain how the basicity of amines varies
More informationammonium 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 informationChapter 22 Amines. Nomenclature Amines are classified according to the degree of substitution at nitrogen.
CH. 22 Chapter 22 Amines Amines are very important in biological chemistry. Most of the bases in biological acid-base reactions are amines. They are also very important nucleophiles in biochemical reactions.
More informationChemistry II (Organic)
Chemistry II (rganic) eteroaromatic Chemistry LECTURE 8 (Iso)quinolines & diazines: properties, syntheses & reactivity Alan C. Spivey a.c.spivey@imperial.ac.uk Mar 0 Format & scope of lecture 8 pyrrole
More informationCHEM 234: Organic Chemistry II Reaction Sheets
EM234:rganichemistry eactionsheets ucleophilic addition at carbonyl groups: Grignards and reducing agents u: u u u: u u = or = or l u u u ucleophilic addition at carbonyl groups: oxygen and nitrogen nucleophiles:
More information16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Based on McMurry s Organic Chemistry, 7 th edition
16. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry, 7 th edition Substitution Reactions of Benzene and Its Derivatives Benzene is aromatic: a cyclic conjugated
More informationAmines. Introduction Organic derivatives of ammonia. Many are biologically active.
Amines Introduction Organic derivatives of ammonia. Many are biologically active. 1 Biological Activity Neurotransmitters: dopamine Bioregulators: epinephrine Vitamins: niacin, B 6 Alkaloids: nicotine,
More informationDownloaded from
Page 1 of 6 AMINES Amines are derivatives of ammonia (NH3), obtained by replacement of 1, 2 or all the 3 hydrogen atoms by alkyl and/or aryl groups. In nature amines are present in - proteins, vitamins,
More informationAmines. Amines are bases usually the base involved in biochemical acid-base reactions.
Amines Amines Amines are derivatives of ammonia. Amines are bases usually the base involved in biochemical acid-base reactions. Vitamins comes from the term vital amines - not all vitamins are amines.
More informationSynthesis of Amines Amine Alkylation by SN2 reaction II. Reductive Amination
Synthesis of Amines I. Amine Alkylation by SN2 reaction Amines can be alkylated in SN2 fashion by alkyl halides; primary halides are best for this purpose. This is not a practical reaction for formation
More informationLecture 28 Organic Chemistry 1
CEM 232 rganic Chemistry I University of Illinois at ChicagoUIC Lecture 28 rganic Chemistry 1 Professor Duncan Wardrop April 22, 2010 1 Today s Lecture Topics Covered: 1. Aryl alides - Bonding, Physical
More informationClass XII: Chemistry Chapter 13: Amines Top concepts
Class XII: Chemistry Chapter 13: Amines Top concepts 1. Amines are regarded as derivatives of ammonia in which one, two or all three hydrogen atoms are replaced by alkyl or aryl group 2. Classification
More informationElectrophilic Aromatic Substitution
Electrophilic Aromatic Substitution Chemistry 391 10/14/02 Lecture 5 Diazonium Salts OH NH 2 NaNO 2 aq. HCl N N Cl H 2 O HCl Cl + H 3 O + Chemistry 391 10/16/02 Diazonium Salts The -N + 2 group of an arenediazonium
More informationMODULE I (INORGANIC CHEMISTRY) 1. Coordination Chemistry: 10 Hrs. IUPAC Nomenclature of Co-ordination Compounds :
GOVERNMENT COLLEGE (AUTONOMOUS), RAJAMAHENDRAVARAM DEPARTMENT OF CHEMISTRY New CBCS Syllabus for B.Sc. III Year Effective from 2018 2019 onwards Paper V Semester V Syllabus Applied Inorganic Chemistry
More informationChemistry of Carbonyl Compounds
Chemistry of Carbonyl Compounds ucleophilic addition (1,2-add) / substitution Conjugate addition (1,4 add) obinson annulation (McM 23.12) Alkylation of enolate anions namines as enolate equivs. (McM 23.11)
More informationReactions 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 information16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2
16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based
More information16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2
16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based
More informationDisconnect the carbon heteroatom bonds first
86 44. Aromatic heterocycles 2: synthesis Allopurinol was discussed in Chapter 4, p. 000. ammonia under pressure to give a simple pyridine. The yield is only about 50%, but what does that matter in such
More informationLecture Notes Chemistry 342 Mukund P. Sibi Lecture 33 Amines
Lecture otes Chemistry 342 Mukund P. Sibi Amines Amines are organic compounds derived from ammonia. The nitrogen in amines contains a lone pair of electrons. The presence of this lone pair of electrons
More informationChapter 5 N S. Typical Reactivity of Pyridines, Quinolines and Isoquinolines
Chapter 5 S Typical Reactivity of Pyridines, Quinolines and Isoquinolines 1 2 Typical Reactivity of Pyridines pyridines are much less susceptible to electrophilic substitution than benzene and much more
More informationUnit 13-NITROGEN CONTAINING ORGANIC COMPOUNDS
Unit 13-NITROGEN CONTAINING ORGANIC COMPOUNDS Two marks: 1. Name the product obtained when a nitrile is reduced by H 2 /Ni,. Give the equation. H 2 /Ni, Primary amine: RCN RCH 2 NH 2. 2. How is nitrobenzene
More informationCHAPTER 12. Substituted Benzene
CHAPTER 12 Substituted Benzene 12.1 Alkylbenzenes (Ar-R) Bezylic carbons: CH 3 CH 2 CH 3 CH(CH 3 ) 2 1 Reactions of Alkylbenzens 1. Free Radical Halogenation CH 2 CH 3 Br 2 hv Br CHCH 3 2 2- xidation R
More informationSAR. Structure - Activity Relationships (alkoholy, amíny, aldehydy, ketóny, estery, amidy, kyseliny, uhľovodíky) 2/28/2016
Structure Activity elationships (SA) identifies which functional groups are important for binding and activity SA Structure - Activity elationships (alkoholy, amíny, aldehydy, ketóny, estery, amidy, kyseliny,
More informationChemistry II (Organic)
Chemistry II (rganic) 1 eteroaromatic Chemistry LECTUE 8 Diazoles & diazines: properties, syntheses & reactivity Alan C. Spivey a.c.spivey@imperial.ac.uk Mar 2012 Format & scope of lecture 8 2 Diazoles:
More informationAMINES. 3. Secondary When two hydrogen atoms are replaced by two alkyl or aryl groups.
AMINES Amine may be regarded as derivative of ammonia formed by replacement of one or more hydrogen atoms by corresponding number of alkyl or aryl group CLASSIFICATION 1. Ammonia 2. Primary amine 3. Secondary
More informationInfrared Characteristic Group Frequencies
Infrared Characteristic Group Frequencies Tables and Charts Second Edition GEORGE SOCRATES Brunei, The University of West London, Middlesex, United Kingdom JOHN WILEY & SONS Chichester New York Brisbane
More informationReactions of Benzene Reactions of Benzene 1
Reactions of Benzene Reactions of Benzene 1 2 Halogenation of Benzene v Benzene does not react with Br 2 or Cl 2 unless a Lewis acid is present (a catalytic amount is usually enough) 3 v Mechanism v Mechanism
More informationAmines. Many low molecular weight amines have foul odors.
1 Amines เอกสารประกอบการสอน รายว ชา 01403224 ดร.นงพงา จร สโสภณ Morphine 2 Interesting and Useful Amines Many low molecular weight amines have foul odors. Trimethylamine [(CH 3 ) 3 N], formed when enzymes
More informationChapter 20 Amines 胺类
Amines ORGAIC CEMISTRY 20.1 omenclature ORGAIC CEMISTRY Amines are classified as primary (R 2 ), secondary (R 2 ), or tertiary (R 3 ), depending on the number of organic substituents attached to nitrogen.
More informationChapter 15: Reactions of Substituted Benzenes
Learning Objectives: Chapter 15: Reactions of Substituted Benzenes 1. Be able to recognize and utilize the oxidative and reductive reactions involving the substituents on benzene. 2. Recognize whether
More informationKOT 222 Organic Chemistry II
KOT 222 Organic Chemistry II Course Objectives: 1) To introduce the chemistry of alcohols and ethers. 2) To study the chemistry of functional groups. 3) To learn the chemistry of aromatic compounds and
More informationSuggested solutions for Chapter 30
s for Chapter 30 30 PRBLEM 1 uggest a mechanism for this synthesis of a tricyclic aromatic heterocycle. 2 Cl base A simple exercise in the synthesis of a pyridine fused to a pyrrole (or an indole with
More informationChapter 09 Benzene and Its Derivatives
Chapter 09 Benzene and Its Derivatives Benzene First isolated in 1825 from whale oil by Michael Faraday Unsaturated hydrocarbon but did not have the typical reactivity of alkenes or alkynes. CM 240: Fall
More informationCh.16 Chemistry of Benzene: Electrophilic Aromatic Substitution
Ch.16 Chemistry of Benzene: Electrophilic Aromatic Substitution Electrophilic aromatic substitution: E + E + + Some electrophilic aromatic substitution: X N 2 S 3 R C R alogenation Nitration Sulfonation
More informationTop concepts Chapter: Amines 1. Amines are regarded as derivatives of ammonia in which one, two or all three hydrogen atoms are replaced by alkyl or aryl group 2. Classification of amines: 3. Preparation
More informationOrganic Chemistry. M. R. Naimi-Jamal. Faculty of Chemistry Iran University of Science & Technology
Organic Chemistry M. R. Naimi-Jamal Faculty of Chemistry Iran University of Science & Technology Chapter 5-2. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry,
More informationCHAPTER 16 - CHEMISTRY OF BENZENE: ELECTROPHILIC AROMATIC SUBSTITUTION
CAPTR 16 - CMISTRY F BNZN: LCTRPILIC ARMATIC SUBSTITUTIN As stated in the previous chapter, benzene and other aromatic rings do not undergo electrophilic addition reactions of the simple alkenes but rather
More informationExamples of Substituted Benzenes
Organic Chemistry 5 th Edition Paula Yurkanis Bruice Examples of Substituted Benzenes Chapter 15 Reactions of Substituted Benzenes Irene Lee Case Western Reserve University Cleveland, OH 2007, Prentice
More informationChapter 13 Reactions of Arenes Electrophilic Aromatic Substitution
. 13 hapter 13 eactions of Arenes lectrophilic Aromatic ubstitution lectrophiles add to aromatic rings in a fashion somewhat similar to the addition of electrophiles to alkenes. ecall: 3 4 Y 1 4 2 1 δ
More informationThe now-banned diet drug fen-phen is a mixture of two synthetic substituted benzene: fenfluramine and phentermine.
The now-banned diet drug fen-phen is a mixture of two synthetic substituted benzene: fenfluramine and phentermine. Chemists have synthesized compounds with structures similar to adrenaline, producing amphetamine.
More informationORGANIC - BROWN 8E CH. 22- REACTIONS OF BENZENE AND ITS DERIVATIVES
!! www.clutchprep.com CONCEPT: ELECTROPHILIC AROMATIC SUBSTITUTION GENERAL MECHANISM Benzene reacts with very few reagents. It DOES NOT undergo typical addition reactions. Why? If we can get benzene to
More informationCHEM 303 Organic Chemistry II Problem Set III Chapter 14 Answers
CHEM 303 rganic Chemistry II Problem Set III Chapter 14 Answers 1) Give the major products of each of the following reactions. If a mixture is expected, identify the major product. + H 3 CHC CHCH 3 H 2
More information10. Amines (text )
2009, Department of Chemistry, The University of Western Ontario 10.1 10. Amines (text 10.1 10.6) A. Structure and omenclature Amines are derivatives of ammonia (H 3 ), where one or more H atoms has been
More informationStructure and Reactivity: Prerequired Knowledge
Structure and eactivity: Prerequired Knowledge!!! The concepts presented in this summary are required for lecture and examination!!! 1. Important Principles in rganic Chemistry In general, structures which
More informationChapter 20 Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution
ucleophilic Acyl Substitution hapter 20 arboxylic Acid Derivatives ucleophilic Acyl Substitution Y (1) need to have Y as a u Y u u + Y (2) could not happen with aldehydes or ketones as : and : are poor
More informationChapter 15 Amines Amines 15.2 Naming Amines 15.3 Physical Properties of Amines
Chapter 15 Amines 15.1 Amines 15.2 Naming Amines 15.3 Physical Properties of Amines 1 Amines Amines are organic compounds in which one or more H in ammonia, NH 3, is replaced with alkyl or aromatic groups.
More informationChapter 21. Organic Chemistry 4 th Edition Paula Yurkanis Bruice. More About Amines. Heterocyclic Compounds
Organic Chemistry 4 th Edition Paula Yurkanis Bruice Chapter 21 More About Amines. Heterocyclic Compounds Irene Lee Case Western Reserve University Cleveland, OH 2004, Prentice Hall Amines An amine is
More informationHeterocyclic Chemistry
eterocyclic Chemistry S Chapter 10:Pyrroles, eactions and Synthesis M.. aimi-jamal Pyrroles: eactions and Synthesis Based n: J. A. Joule & K. Mills s eterocyclic Chemistryocyclic Chemistry Pyrrole and
More informationMore EAS. Lecture 12. Di- and Polysubstitution CH 3 + H + H HNO 2 NO 2. February 25, /25/16 OCH 3 OCH OCH. o-nitro-anisole (31%) Anisole
Lecture 12 More EAS February 25, 2016 Di- and Polysubstitution O O OC OC 3 3 NO 3 2 SO 4 Anisole o-nitro-anisole (31%) m-nitro-anisole (2%) p-nitro-anisole (67%) l -O is ortho-para directing and activating
More informationAryl Halides. Structure
Aryl Halides Structure Aryl halides are compounds containing halogen attached directly to an aromatic ring. They have the general formula ArX, where Ar is phenyl, substituted phenyl. X= F,Cl,Br,I An aryl
More informationOrganic Tutorials 3 rd Year Xmas Vac
rganic Tutorials 3 rd Year Xmas Vac Third Year Reactive Intermediates: Radicals, Arynes, Carbenes etc. Radicals References: Moody and Whitham Reactive Intermediates, xford Chemistry Primer 8; Carey and
More informationPAPER No. 5: REACTION MECHANISM MODULE No. 2: Types of Organic Reaction Mechanisms
Subject Chemistry Paper No and Title Module No and Title Module Tag Paper No. 5:Organic Chemistry-II Module No. 2: Overview of different types of Organic Reaction Mechanisms CHE_P5_M2 TABLE OF CONTENTS
More informationChem 263 Oct. 12, 2010
Chem 263 ct. 12, 2010 Alkyl Side Chain xidation Reaction If the carbon directly attached to the aromatic ring has > 1 hydrogen attached to it, it can be oxidized to the corresponding carboxylic acid with
More information6.10 Amines. Naming. N Goalby chemrevise.org 1 CH2 CH2
6.10 Amines aming Amines These end in amine. There is, however, rather confusingly two ways of using this suffix. The exam board tend to use the common version where the name stem ends in -yl propylamine.
More information11/26/ Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds
9.5 Polycyclic Aromatic Compounds The general concept of aromaticity can be extended to include polycyclic aromatic compounds Benzo[a]pyrene is one of the cancer-causing substances found in tobacco smoke
More informationChapter 16 Chemistry of Benzene: Electrophilic Aromatic Substitution
John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 16 Chemistry of Benzene: Electrophilic Aromatic Substitution Paul D. Adams University of Arkansas Substitution Reactions of Benzene and Its Derivatives
More informationChem 263 Nov 24, Properties of Carboxylic Acids
Chem 263 ov 24, 2009 Properties of Carboxylic Acids Since carboxylic acids are structurally related to both ketones and aldehydes, we would expect to see some similar structural properties. The carbonyl
More informationChem 345 Reaction List: Chem 343 Reactions: Page 1 (You do not need to know the mechanism for the reactions in the boxes).
Chem 345 eaction List: Chem 343 eactions: Page 1 (You do not need to know the mechanism for the reactions in the boxes). uc - optically active LG 2 optically active uc Alpha carbon (carbon attached to
More informationDr. Mohamed El-Newehy
By Dr. Mohamed El-Newehy Chemistry Department, College of Science, King Saud University http://fac.ksu.edu.sa/melnewehy Amines 1 Classification and Structure of Amines -The relation between ammonia and
More informationReactions at α-position
Reactions at α-position In preceding chapters on carbonyl chemistry, a common reaction mechanism observed was a nucleophile reacting at the electrophilic carbonyl carbon site NUC NUC Another reaction that
More informationSeptember [KV 804] Sub. Code: 3804
September 2009 [KV 804] Sub. Code: 3804 (Regulations 2008-2009) (Candidates admitted from 2008-2009 onwards) Paper IV PHARMACEUTICAL ORGANIC CHEMISTRY Time : Three hours Maximum : 70 marks Answer All questions
More informationChapter 16: Aromatic Compounds
Chamras Chemistry 106 Lecture otes xamination 2 Materials Chapter 16: Aromatic Compounds Benzene, the Most Commonly Known Aromatic Compound: The aromatic nature of benzene stabilizes it 36 kcal.mol 1.
More informationSynthetic possibilities Chem 315 Beauchamp 1
Synthetic possibilities hem Beauchamp Propose reasonable syntheses f the following target molecules (TM-#). You can use the given starting materials and any typical ganic reagents studied in our course
More informationHighlights of Schmidt Reaction in the Last Ten Years
ighlights of Schmidt eaction in the Last Ten Years Dendrobates histrionicus Jack Liu ov. 18, 2003 Introduction Classical Schmidt reaction of aldehydes and carboxylic acids Classical Schmidt reaction of
More information22.7 Reactions of Amines: A Review and a Preview
22.7 Reactions of Amines: A Review and a Preview Preparation of Amines Two questions to answer: 1) How is the C N C N bond to be formed? 2) How do we obtain the correct oxidation state of nitrogen (and
More information.. Amines CHAPTER SUMMARY
10 N.. N.. CHAPTER SUMMARY 10.1 Structure of are derivatives of ammonia in which one or more hydrogens have been replaced by organic groups. Replacement of one hydrogen results in a primary amine. In a
More information