Amines and Heterocycles. McMurry: Chapter 24
|
|
- Cornelia Stafford
- 6 years ago
- Views:
Transcription
1 Amines and Heterocycles McMurry: Chapter 24
2 Introduction to Amines and Heterocycles Amines and heterocycles (cyclic amines) are ammonia derivatives, many of whichare found widely in livingorganisms: 2
3 Colourful Amines and Heterocycles Nature has inspired chemists to duplicate natural dyes and create new synthetic ones to introduce colour to our world: King George VI O H N Br Br N H O - purpura molluscs 3
4 Heterocyclic c Amines Heterocycles are cyclic compounds containing at least one heteroatom: 4
5 Heterocyclic c Amines Heterocycles are found in many natural products that exhibit useful biologicalactivityactivity and in widely used pharmaceuticals: 5
6 Amine Nomenclature Amines are named by added the suffix amine, but in more complex compounds, the amine can be an amino substituent or an aniline derivative: Complex compounds are treated as alkanamines with simpler alkylgroups on the amine identified with the locant N : N 6
7 Take Home: ae e: Nomenclature catu e Draw the following compounds: 4 bromo N isopropyl 3 methylaniline (R,E) oct 6 en 3 amine 7
8 Amine Structure and Properties Alkyl amines have an sp 3 N with approximately tetrahedral geometry. The N H groups participate ii in hd hydrogen bonding: Small amines have a bad odor resembling fish/decaying i material: 8
9 Basicity of Alkyl Amines Amines have a lone pair of electrons on the nitrogen that make them both hbasic and nucleophilic in nature: Nucleophilic amine: Basic amine: ammonium salt ammonium salt The relative base strengths of amines are calculated using the pk a of the ammonium salt! 9
10 Basicity of Amines ammonium salt weak conjugate base (NR 3 ) Low pk a (strong acid) strong conjugate base (NR 3 3) High pk a (weak acid) stronger base weaker base 10
11 Explaining Relative Basicity of Amines Amides are non basic and non nucleophilic due to resonance with the carbonyl: Aryl amines are less basic than alkyl amines due to electron delocalization into the aromatic ring: 11
12 Basicity of Aryl Amines Substituents on the aromatic ring varies the amine basicity: Electron donors: increase basicity adds electron density to nitrogen Electron withdrawing: decrease basicity withdraws electron density from nitrogen strong base weak base 12
13 IR Spectroscopy of Amines N H stretch: cm 1 R 2 NH have 1 band while RNH 2 have 2 bands sharper and less intense than O H stretch 13
14 NMR Spectroscopy ofamines 13 C NMR: Carbons attached to amines are deshielded and are found between ppm. 1 H NMR: RNH: variable chemical shift ( ppm, broad singlet) R 2 CHNH: deshielded and found in the ppm range 2 14
15 Amine Synthesis: S N 2 Reactions Amines are good nucleophiles, so they readily participate in S N 2 reactions with alkyl halides: N 15
16 Amine Synthesis: S N 2 Reactions How can S N 2 reactivity be limited? Use a large excess of amine to maximize i monoalkylation: l N How can the excessive S N 2 reactivity it be made and utilized? If the quaternary salt is desired, use excess alkylating reagent: 16
17 Alkyl Amine Reactivity: ty: Hofmann Elimination Amines (like alcohols) can be eliminated to give alkenes. Just like H 2 O is a better leaving group than OH, the amide ion ( NH 2 ) must be converted to a better LG for elimination to occur: 17
18 Alkyl Amine Reactivity: ty: Hofmann Elimination Elimination of the ammonium salt is promoted by silver oxide, which exchanges the iodide ion for a hydroxide ion. Then, an E2 reaction occurs to give the less substituted alkene due to sterics: 18
19 Synthesis Problems Predict the products of the following Hofmann elimination reactions: *
20 Amine Synthesis: Azides Azide ions ( N 3 ) are useful alternatives to NH 3 since they only undergo S N 2 reactivity ii once and can be reduced dto 1 amines: 3 N alkyl azide
21 Amine Synthesis: Gabriel Synthesis The Gabriel synthesis of 1 amines utilizes phthalimide alkylation l and imide id hd hydrolysis steps: N phthalimide
22 Take Home ae emechanism Problem Draw the imide hydrolysis mechanism: *Hint: an imide is just like 2 amide functional groups! 22
23 Amine Synthesis: Reductive Amination Reductive amination is another common amine synthesis whichinvolves involves converting an aldehyde or ketone to an imine and then reduced it with sodium cyanoborohydride: H H B H Na CN O NaBH 3 CN OH O 3 H very slow NH NaBH 3 CN NH 2 H very fast 23
24 Synthesis s Problems Complete the following Gabriel synthesis: 24
25 Take Home ae esynthesis s Problems Predict the starting material or product in the following reactions: 25
26 Aryl Amine Reactivity: ty: Diazonium ao Salts When aryl amines are treated with nitrous acid (made in situ), the reaction produces very useful and reactive intermediates called diazonium salts: Diazonium salts from alkyl l amines cannot be used since they spontaneously decompose! 26
27 Diazonium ao Salts in Sandmeyer Reactions Diazonium salts are useful because they can be replaced with a variety of substituents including halides in Sandmeyer reactions: The mechanism is believed to occur via radical intermediates. 27
28 Diazonium ao Salts in S E Ar Reactions Diazonium salts also couple with phenols and anilines in an S E Ar reaction to give azo compounds: 28
29 y Connections Chemistry Azo Compounds: Keeping Things Colourful! Azo compounds have extended conjugation so they absorb in the visible region, which we perceive as colour: Small structural changes to the azo compound allows a variety of colours to be made. These compounds p are used widelyy as dyes y ((called azo dyes) for textiles, paint, food, cosmetics, and indicators. 29
30 In Class CassSynthesis s Problem Predict the products of the following reactions:
31 Take Home ae esynthesis s Problem * Propose a synthesis for the following compounds using benzene and phenol as your starting materials: 31
Chapter 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 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 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 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 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 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. 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 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 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 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 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 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 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 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 informationAMINES. 3. From your knowledge of the effects involved, predict or explain experimental results. Important areas include:
AMINES A STUDENT SHOULD BE ABLE TO: 1. Name given the structure, and draw the structure given the name of amines and common nitrogen heterocycles (pyrrole and pyridine). Also, give the classification of
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 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 informationAmines. 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 informationQuestion 13.1: Classify the following amines as primary, secondary or tertiary: (i) (ii) (iii) (C 2 H 5 ) 2 CHNH 2 (iv) (C 2 H 5 ) 2 NH Primary: (i) and (iii) Secondary: (iv) Tertiary: (ii) Question 13.2:
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 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 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 informationChapter 20: Carboxylic Acids and Nitriles شیمی آلی 2
Chapter 20: Carboxylic Acids and Nitriles شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry s Organic Chemistry, 7 th edition The
More information21.1 Introduction Carboxylic Acids Nomenclature of Carboxylic Acids. Acids Structure and Properties of Carboxylic Acids.
21.1 Introduction Carboxylic Acids Carboxylic acids are abundant in nature and in pharmaceuticals. 21.1 Introduction Carboxylic Acids The US produces over 2.5 million tons of acetic acid per year, which
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 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 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 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 informationAMINES. 4. From your knowledge of the effects involved, predict or explain experimental results. Important areas include:
AMINES A STUDENT SHOULD BE ABLE TO: 1. Give the IUPAC or common name given the structure, and draw the structure given the name of amines and common nitrogen heterocycles (pyrrole, pyridine, purine, pyrimidine,
More informationCarboxylic Acids and Nitriles
Carboxylic Acids and Nitriles Why this Chapter? Carboxylic acids present in many industrial processes and most biological processes They are the starting materials from which other acyl derivatives are
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 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 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 information٢
Amines ١ ٢ ٣ ٤ ٥ ٦ ٧ ٨ ٩ ١٠ ١١ Physical Properties of Amines - Amines are moderately polar. For this reason the low formula weight amines are readily soluble in water due to the formation of hydrogen bonds
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 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 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 informationChapter AMINES
Chapter - 13 - AMINES Level one 1) Write IUPAC names of the following compounds and classify them into primary,secondary andteritary amines. a) (CH 3) 2CHNH 2 Ans:propan-2-amine(primary) b)ch 3(CH 2) 2NH
More informationChapter 8. Acidity, Basicity and pk a
Chapter 8 Acidity, Basicity and pk a p182 In this reaction water is acting as a base, according to our definition above, by accepting a proton from HCl which in turn is acting as an acid by donating a
More informationAdditions to the Carbonyl Groups
Chapter 18 Additions to the Carbonyl Groups Nucleophilic substitution (S N 2andS N 1) reaction occurs at sp3 hybridized carbons with electronegative leaving groups Why? The carbon is electrophilic! Addition
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 informationCarboxylic Acids O R C + H + O - Chemistry 618B
arboxylic Acids R H R + H + - R - Nomenclature - IUPA IUPA names: drop the -e from the parent alkane and add the suffix -oic acid If the compound contains a carbon-carbon double bond, change the infix
More informationBenzylamine reacts with nitrous acid to form unstable diazonium salt, which in turn gives alcohol with the evolution of nitrogen gas.
Benzylamine reacts with nitrous acid to form unstable diazonium salt, which in turn gives alcohol with the evolution of nitrogen gas. On the other hand, aniline reacts with HNO2 at a low temperature to
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 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 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 informationChapter 10: Carboxylic Acids and Their Derivatives
Chapter 10: Carboxylic Acids and Their Derivatives The back of the white willow tree (Salix alba) is a source of salicylic acid which is used to make aspirin (acetylsalicylic acid) The functional group
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 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 informationCarbonyl Chemistry V + C O C. Chemistry /30/02
arbonyl hemistry V Ō - + Keto-enol enol Tautomerism H 3 H 3 Ketone H H R 2 H R' H H 3 H 2 H Enol H Acid atalyzed α Halogenation R 2 R' + X 2 H + R 2 R' + HX H X X 2 can be l 2, Br 2, or I 2. Substitution
More informationCHM 292 Final Exam Answer Key
CHM 292 Final Exam Answer Key 1. Predict the product(s) of the following reactions (5 points each; 35 points total). May 7, 2013 Acid catalyzed elimination to form the most highly substituted alkene possible
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 informationAnswers to Assignment #5
Answers to Assignment #5 A. 9 8 l 2 5 DBE (benzene + 1 DBE) ( 9 2(9)+2-9 8+1+1 = 10 ˆ 5 DBE) nmr pattern of two doublets of equal integration at δ7.4 and 7.9 ppm means the group (the δ7.9 shift) IR band
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 information22.1 Amine Nomenclature
Chapter 22 Amines 22.1 Amine Nomenclature Classification of Amines Alkylamine N attached to alkyl group Arylamine N attached to aryl group Primary, secondary, or tertiary determined by number of carbon
More informationChemistry Questions ans Answers BASED ON HIGH ORDER THINKING SKILL (HOTS) UNIT- 13 ORGANIC COMPOUNDS CONTAINING NITROGEN
Chemistry Questions ans Answers BASED N HIGH RDER THINKING SKILL (HTS) UNIT- 13 RGANIC CMPUNDS CNTAINING NITRGEN 1 MARK QUESTINS Q. 1. Why the presence of a base is essential in the ammonolysis of alkyl
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 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 informationChapter 9 Aldehydes and Ketones Excluded Sections:
Chapter 9 Aldehydes and Ketones Excluded Sections: 9.14-9.19 Aldehydes and ketones are found in many fragrant odors of many fruits, fine perfumes, hormones etc. some examples are listed below. Aldehydes
More informationCape Cod Community College
Cape Cod Community College Departmental Syllabus Prepared by the Department of Natural Sciences & Applied Technology Date of Departmental Approval: February 3, 2014 Date Approved by Curriculum and Programs:
More informationTOPIC 5. AMINES (Chapter 20)
L TPIC 5. AMIES (Chapter 20) BJECTIVES 1. ame aliphatic and aromatic amines 2. Describe the basicity of amines, predict base strength based on structure 3. Recognize nucleophilicity of amines 4. Develop
More informationMCAT Organic Chemistry Problem Drill 10: Aldehydes and Ketones
MCAT rganic Chemistry Problem Drill 10: Aldehydes and Ketones Question No. 1 of 10 Question 1. Which of the following is not a physical property of aldehydes and ketones? Question #01 (A) Hydrogen bonding
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 informationLecture Topics: I. Electrophilic Aromatic Substitution (EAS)
Reactions of Aromatic Compounds Reading: Wade chapter 17, sections 17-1- 17-15 Study Problems: 17-44, 17-46, 17-47, 17-48, 17-51, 17-52, 17-53, 17-59, 17-61 Key Concepts and Skills: Predict and propose
More informationKey ideas: In EAS, pi bond is Nu and undergoes addition.
Objective 7. Apply addition and elimination concepts to predict electrophilic aromatic substitution reactions (EAS) of benzene and monosubstituted benzenes. Skills: Draw structure ID structural features
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 informationCHEMISTRY 263 HOME WORK
Lecture Topics: CHEMISTRY 263 HOME WORK Module7: Hydrogenation of Alkenes Hydrogenation - syn and anti- addition - hydrogenation of alkynes - synthesis of cis-alkenes -synthesis of trans-alkenes Text sections:
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 informationAMINES. Unit Write IUPAC names of the following :
Unit - 13 AMINES 1. Write IUPAC names of the following : 2. Giving an example of each, describe the following reactions : Hoffman bromamide reaction Gabriel phthanlimide synthesis Gatterman reaction Coupling
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 17. Carbonyl Compounds I Nucleophilic Acyl Substitution
Chapter 17. Carbonyl Compounds I Nucleophilic Acyl Substitution Carbonyl compounds: compounds containing C=O group. 1. Class I carbonyl compounds: Carboxylic acids and derivatives containing a group (
More informationModule9. Nuclear Magnetic Resonance Spectroscopy Nuclear Magnetic Resonance (NMR) spectroscopy - Chemical shift - Integration of signal area
1 CHEMISTRY 263 HOME WORK Lecture Topics: Module7. Hydrogenation of Alkenes The Function of the Catalyst - Syn and anti- addition Hydrogenation of Alkynes - Syn- addition of hydrogen: Synthesis of cis-alkenes
More informationLearning Guide for Chapter 11 - Alkenes I
Learning Guide for Chapter 11 - Alkenes I I. Introduction to alkenes - p 1 bond structure, classifying alkenes, reactivity, physical properties, occurrences and uses, spectroscopy, stabilty II. Unsaturation
More information24.4: Acidity of Phenols. Phenols are more acidic than aliphatic alcohols. + Electron-withdrawing groups make an O
Chapter 24: Phenols. Alcohols contain an group bonded to an sp 3 -hybridized carbon. Phenols contain an group bonded to an sp 2 -hybridized carbon of a benzene ring 24.1: Nomenclature (please read) 24.2:
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 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 informationName: Student Number: University of Manitoba - Department of Chemistry CHEM Introductory Organic Chemistry II - Term Test 2
Name: Student Number: University of Manitoba - Department of Chemistry CHEM 2220 - Introductory Organic Chemistry II - Term Test 2 Thursday, March 12, 2015; 7-9 PM This is a 2-hour test, marked out of
More information1/4/2011. Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds
Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds The Acidity of the Hydrogens of Carbonyl Compounds: Enolate Anions Hydrogens on carbons to carbonyls are unusually acidic
More informationSynthesis of Nitriles a. dehydration of 1 amides using POCl 3 : b. SN2 reaction of cyanide ion on halides:
I. Nitriles Nitriles consist of the CN functional group, and are linear with sp hybridization on C and N. Nitriles are non-basic at nitrogen, since the lone pair exists in an sp orbital (50% s character
More informationN_HW1 N_HW1. 1. What is the purpose of the H 2 O in this sequence?
N_HW1 N_HW1 Multiple Choice Identify the choice that best completes the statement or answers the question. There is only one correct response for each question. 1. What is the purpose of the H 2 O in this
More informationWhat happens when methanamine reacts with FeCl 3? Methylamine in water reacts with FeCl 3 to givebrown precipitate of hydrated ferric oxide:
What happens when methanamine reacts with FeCl 3? Methylamine in water reacts with FeCl 3 to givebrown precipitate of hydrated ferric oxide: Due to the electron donating inductive or +I effect of CH 3
More informationHyperlearning MCAT Instructor Qualifying Exam Organic Chemistry
Hyperlearning MCAT Instructor Qualifying Exam Organic Chemistry 30 Questions (5 pages); Time limit = 45 minutes Use of books or notes is not permitted. 1. When analyzed with a polarimeter, which of the
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 informationSome..(A) Describe the synthesis of azo dyes and the full chemical equations for each step.
A2 Chemistry: F324 Rings, Polymers and Analysis Amines Learning Outcomes: All.. (E) Most.. (C) Explain why amines are basic Draw the structure of a primary secondary and tertiary amine Describe the reactions
More information11/30/ Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions
Chapter 9 Problems: 9.1-29, 32-34, 36-37, 39-45, 48-56, 58-59, 61-69, 71-72. 9.8 Substituent effects in the electrophilic substitution of an aromatic ring Substituents affect the reactivity of the aromatic
More informationProperties of Amines
Properties of Amines 1. Boiling Point and Water Solubility It is instructive to compare the boiling points and water solubility of amines with those of corresponding alcohols and ethers. The dominant factor
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 informationTOK: The relationship between a reaction mechanism and the experimental evidence to support it could be discussed. See
Option G: Further organic chemistry (15/22 hours) SL students study the core of these options and HL students study the whole option (the core and the extension material). TOK: The relationship between
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 informationOCR (A) Chemistry A-level. Module 6: Organic Chemistry and Analysis
OCR (A) Chemistry A-level Module 6: Organic Chemistry and Analysis Organic Synthesis Notes by Adam Robertson DEFINITIONS Heterolytic fission: The breaking of a covalent bond when one of the bonded atoms
More informationChem 263 March 28, 2006
Chem 263 March 28, 2006 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 informationREACTIONS OF AROMATIC COMPOUNDS
A STUDENT SHOULD BE ABLE TO: REACTIONS OF AROMATIC COMPOUNDS 1. Predict the product(s) of Electrophilic aromatic substitution (EAS): halogenation, sulfonation, nitration, Friedel- Crafts alkylation and
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 Chemistry II KEY March 25, a) I only b) II only c) II & III d) III & IV e) I, II, III & IV
rganic Chemistry II KEY March 25, 2015 Exam 2: VERSIN A 1. Which of the following compounds will give rise to an aromatic conjugate base? E a) I only b) II only c) II & III d) III & IV e) I, II, III &
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 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 informationInfrared Spectroscopy
Infrared Spectroscopy Introduction Spectroscopy is an analytical technique which helps determine structure. It destroys little or no sample. The amount of light absorbed by the sample is measured as wavelength
More informationExam 1 (Monday, July 6, 2015)
Chem 231 Summer 2015 Assigned Homework Problems Last updated: Friday, July 24, 2015 Problems Assigned from Essential Organic Chemistry, 2 nd Edition, Paula Yurkanis Bruice, Prentice Hall, New York, NY,
More informationChapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions
Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry s Organic
More informationCHE1502. Tutorial letter 203/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry
E1502/203/1/2016 Tutorial letter 203/1/2016 General hemistry 1B E1502 Semester 1 Department of hemistry This tutorial letter contains the answers to the questions in assignment 3. FIRST SEMESTER: KEY T
More information