22.7 Reactions of Amines: A Review and a Preview
|
|
- Iris Lester
- 6 years ago
- Views:
Transcription
1 22.7 Reactions of Amines: A Review and a Preview
2 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 carbon)?
3 Methods for C N C N Bond Formation Nucleophilic substitution by azide ion (N 3 ) (Section 8.1, 8.13) Nitration of arenes (Section 12.3) Nucleophilic ring opening of epoxides by ammonia (Section 16.12) Nucleophilic addition of amines to aldehydes and ketones (Sections 17.10, 17.11) Nucleophilic substitution by ammonia on a-halo a acids (Section 19.16) Nucleophilic acyl substitution (Sections 20.3, 20.5, and 20.11) Hofmann rearrangement (Section 20.17)
4 22.8 Preparation of Amines by Alkylation of Ammonia
5 Desired reaction is: Alkylation of Ammonia 2 NH 3 + R X R NH 2 + NH 4 X
6 Desired reaction is: Alkylation of Ammonia 2 NH 3 + R X R NH 2 + NH 4 X via: H 3 N X + X + R H 3 N R + then: H H 3 N + H + N R + H 3 N H + N H R H H
7 Alkylation of Ammonia But the method doesn't work well in practice. Usually gives a mixture of primary, secondary, and tertiary amines, plus the quaternary salt. NH 3 RX RNH 2 RX R 2 NH R 4 N + X RX R 3 N RX
8 Example CH 3 (CH 2 ) 6 CH 2 Br NH 3 CH 3 (CH 2 ) 6 CH 2 NH 2 As octylamine is formed, it competes with ammonia for the remaining 1-bromooctane. 1 Reaction of octylamine with 1-bromooctane 1 gives N,N-dioctylamine.
9 Example CH 3 (CH 2 ) 6 CH 2 Br NH 3 CH 3 (CH 2 ) 6 CH 2 NH 2 (45%) + CH 3 (CH 2 ) 6 CH 2 NHCH 2 (CH 2 ) 6 CH 3 (43%) As octylamine is formed, it competes with ammonia for the remaining 1-bromooctane. 1 Reaction of octylamine with 1-bromooctane 1 gives N,N-dioctylamine.
10 22.9 The Gabriel Synthesis of Primary Alkylamines
11 Gabriel Synthesis gives primary amines without formation of secondary, etc. amines as byproducts uses an S N 2 reaction on an alkyl halide to form the C N C N bond the nitrogen-containing nucleophile is N-potassiophthalimide
12 Gabriel Synthesis gives primary amines without formation of secondary, etc. amines as byproducts uses an S N 2 reaction on an alkyl halide to form the C N C N bond the nitrogen-containing nucleophile is N-potassiophthalimide N K +
13 N-Potassiophthalimide the pka p a of phthalimide is 8.3 N-potassiophthalimide is easily prepared by the reaction of phthalimide with KH NH KH N K +
14 N-Potassiophthalimide as a nucleophile N + R X S N 2 N R + X
15 Cleavage of Alkylated Phthalimide N R + H 2 acid or base C 2 H C 2 H + imide hydrolysis is nucleophilic acyl substitution H 2 N R
16 Cleavage of Alkylated Phthalimide hydrazinolysis is an alternative method of releasing the amine from its phthalimide derivative N R H 2 NNH 2 NH NH + H 2 N R
17 Example N K + + C 6 H 5 CH 2 Cl DMF
18 Example N K + + C 6 H 5 CH 2 Cl DMF N CH 2 C 6 H 5 (74%)
19 Example NH NH + C 6 H 5 CH 2 NH 2 H 2 NNH 2 (97%) N CH 2 C 6 H 5
20 22.10 Preparation of Amines by Reduction
21 Preparation of Amines by Reduction almost any nitrogen-containing compound can be reduced to an amine, including: azides nitriles nitro-substituted benzene derivatives amides
22 Synthesis of Amines via Azides S N 2 reaction, followed by reduction, gives a primary alkylamine. CH 2 CH 2 Br NaN 3 CH 2 CH 2 N 3 (74%) 1. LiAlH 4 2. H 2 CH 2 CH 2 NH 2 (89%)
23 Synthesis of Amines via Azides S N 2 reaction, followed by reduction, gives a primary alkylamine. CH 2 CH 2 Br NaN 3 CH 2 CH 2 N 3 azides may also be reduced by catalytic hydrogenation (74%) 1. LiAlH 4 2. H 2 CH 2 CH 2 NH 2 (89%)
24 Synthesis of Amines via Nitriles S N 2 reaction, followed by reduction, gives a primary alkylamine. CH 3 CH 2 CH 2 CH 2 Br NaCN CH 3 CH 2 CH 2 CH 2 CN (69%) H 2 (100 atm), Ni CH 3 CH 2 CH 2 CH 2 CH 2 NH 2 (56%)
25 Synthesis of Amines via Nitriles S N 2 reaction, followed by reduction, gives a primary alkylamine. CH 3 CH 2 CH 2 CH 2 Br NaCN CH 3 CH 2 CH 2 CH 2 CN nitriles may also be reduced by lithium aluminum hydride (69%) H 2 (100 atm), Ni CH 3 CH 2 CH 2 CH 2 CH 2 NH 2 (56%)
26 Synthesis of Amines via Nitriles S N 2 reaction, followed by reduction, gives a primary alkylamine. CH 3 CH 2 CH 2 CH 2 Br NaCN CH 3 CH 2 CH 2 CH 2 CN the reduction also works with cyanohydrins (69%) H 2 (100 atm), Ni CH 3 CH 2 CH 2 CH 2 CH 2 NH 2 (56%)
27 Synthesis of Amines via Nitroarenes Cl HN 3 H 2 S 4 Cl N 2 (88-95%) 1. Fe, HCl 2. NaH Cl NH 2 (95%)
28 Synthesis of Amines via Nitroarenes Cl HN 3 H 2 S 4 Cl N 2 nitro groups may also be reduced with tin (Sn) + HCl or by catalytic hydrogenation (88-95%) 1. Fe, HCl 2. NaH Cl NH 2 (95%)
29 Synthesis of Amines via Amides CH 1. SCl 2 2. (CH 3 ) 2 NH (86-89%) 89%) CN(CH 3 ) 2 1. LiAlH 4 2. H 2 CH 2 N(CH 3 ) 2 (88%)
30 Synthesis of Amines via Amides CH only LiAlH 4 is an appropriate reducing agent for this reaction 1. SCl 2 2. (CH 3 ) 2 NH (86-89%) 89%) 1. LiAlH 4 2. H 2 CN(CH 3 ) 2 CH 2 N(CH 3 ) 2 (88%)
31 22.11 Reductive Amination
32 Synthesis of Amines via Reductive Amination In reductive amination, an aldehyde or ketone is subjected to catalytic hydrogenation in the presence of ammonia or an amine. R fast R C + NH 3 C NH + H 2 R' R' The aldehyde or ketone equilibrates with the imine faster than hydrogenation occurs.
33 Synthesis of Amines via Reductive Amination The imine undergoes hydrogenation faster than the aldehyde or ketone. An amine is the product. R fast R C + NH 3 C NH + H 2 R' R' R C NH 2 R' H 2, Ni H
34 Example: Ammonia gives a primary amine. + NH 3 H 2, Ni ethanol H NH 2 (80%) via: NH
35 Example: Primary amines give secondary amines CH 3 (CH 2 ) 5 CH + H 2 N H 2, Ni ethanol CH 3 (CH 2 ) 5 CH 2 NH (65%)
36 Example: Primary amines give secondary amines CH 3 (CH 2 ) 5 CH + H 2 N H 2, Ni ethanol CH 3 (CH 2 ) 5 CH 2 NH (65%) via: CH 3 (CH 2 ) 5 CH N
37 Example: Secondary amines give tertiary amines CH 3 CH 2 CH 2 CH H 2, Ni, ethanol + N H N CH 2 CH 2 CH 2 CH 3 (93%)
38 Example: Secondary amines give tertiary amines possible intermediates include: H N CHCH 2 CH 2 CH 3 N+ CHCH 2 CH 2 CH 3 N CH CHCH 2 CH 3
20.5 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 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 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 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 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 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 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 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 informationLecture 23. Amines. Chemistry 328N. April 12, 2016
Lecture 23 Amines April 12, 2016 Michael Reaction Michael reaction: conjugate addition of an enolate Arthur Michael anion to an, -unsaturated carbonyl compound!! Following are two examples in the first,
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 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 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 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 informationROADMAP FOR REACTIONS Chapter 6
RADMAP FR REACTINS Chapter 6 (A) (B) (C) (D) (E) (F) (G) (H) (I) (J) (K) (L) (M) (N) () Regiochemistry: Markovnikov addition to a bond Stereochemistry: anti-addition Regiochemistry: non-markovnikov addition
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 informationMechanisms. . CCl2 F + Cl.
Mechanisms 1) Free radical substitution Alkane à halogenoalkane Initiation: Propagation: Termination: Overall: 2) Ozone depletion UV light breaks the C Cl bond releasing chlorine radical CFCl 3 F à. CCl2
More informationPhysical Properties. Alcohols can be: CH CH 2 OH CH 2 CH 3 C OH CH 3. Secondary alcohol. Primary alcohol. Tertiary alcohol
Chapter 10: Structure and Synthesis of Alcohols 100 Physical Properties Alcohols can be: CH 3 CH 3 CH CH 2 OH * Primary alcohol CH 3 OH CH * CH 2 CH 3 Secondary alcohol CH 3 CH 3 * C OH CH 3 Tertiary alcohol
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 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 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 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 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 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 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 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 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 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 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 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 informationOption G: Further organic chemistry (15/22 hours)
Option G: Further organic chemistry (15/) TOK: The relationship between a reaction mechanism and the experimental evidence to support it could be discussed. See 16... Core material: G1 G8 are core material
More informationThe Claisen Condensation
Lecture 22 The Claisen Condensation CH 3 CCH 2 CH 3 CH 2 CCH 2 CH 3 April 10, 2018 Hydrolysis of Amides Hydrolysis of amides is irreversible. In acid solution the amine product is protonated to give an
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. 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 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 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 informationCOMPOUND CONTAINING NITROGEN. 1) Which will give nitrosoamine when treated with?
COMPOUND CONTAINING NITROGEN 1) Which will give nitrosoamine when treated with? C 6 H 5 NHCH 3 b) H 3 C NH H 3 C H N d) All of these 2) What is the end product in following sequence of reactions? C 2 H
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 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 informationSummary of mechanisms. Type of reaction: Nucleophilic subsitution/hydrolysis
S Summary of mechanisms S Summary of mechanisms electrophilic addition Electrophiles: H δ in H (Ni catalyst needed), H δ in H-X; X δ in X ; H δ in H O (g) (conc H 3 PO 4 cat needed); H δ in NH 3 ; H δ
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 informationCh 20 Carboxylic Acids and Nitriles
Ch 20 Carboxylic Acids and Nitriles Carboxylic Acids (RCO 2 H) are compounds with an OH attached to a carbonyl. Nitriles (RC N) are compounds a carbon-nitrogen triple bond. Naming Carboxylic Acids 1. Replace
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 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 informationALCOHOLS AND PHENOLS
ALCOHOLS AND PHENOLS ALCOHOLS AND PHENOLS Alcohols contain an OH group connected to a a saturated C (sp3) They are important solvents and synthesis intermediates Phenols contain an OH group connected to
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 informationTopic 4.10 ORGANIC SYNTHESIS AND ANALYSIS. Organic analysis Organic synthesis
Topic 4.10 ORGANIC SYNTHESIS AND ANALYSIS Organic analysis Organic synthesis DISTINGUISHING BETWEEN DIFFERENT ORGANIC COMPOUNDS Many of the organic compounds prepared in AS Unit 2 and in A2 Unit 4 can
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 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 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 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 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 informationOrganic Chemistry Review: Topic 10 & Topic 20
Organic Structure Alkanes C C σ bond Mechanism Substitution (Incoming atom or group will displace an existing atom or group in a molecule) Examples Occurs with exposure to ultraviolet light or sunlight,
More informationChapter 12: Carbonyl Compounds II
Chapter 12: Carbonyl Compounds II Learning bjectives: 1. Recognize and assign names to aldehydes and ketones. 2. Write the mechanism for nucleophilic addition and nucleophilic addition-elimination reactions
More informationLECTURE #22 Thurs., Nov.15, 2007
Provide a rxn sequence to make these as the major products Answers: 1. i Pr-Cl, AlCl 3 2. conc. fuming? H 2 S 4 3. Cl 2, FeCl 3 or AlCl 3 4. dilute H 2 S 4 note: normally aqueous workup after step 1, but
More information18.8 Oxidation. Oxidation by silver ion requires an alkaline medium
18.8 Oxidation Oxidation by silver ion requires an alkaline medium Test for detecting aldehydes Tollens reagent to prevent precipitation of the insoluble silver oxide, a complexing agent is added: ammonia
More informationDAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE
DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 6 Dr Ali El-Agamey 1 Oxidation States Easy for inorganic salts: CrO 4 2- reduced to Cr 2 O 3. KMnO 4 reduced to MnO 2. Oxidation: Gain of O,
More informationChapter 20 Carboxylic Acid Derivatives Nucleophilic Acyl Substitution
Chapter 20 Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Nomenclature: In carboxylic acid chlorides, anhydrides, esters and amides, the parent is the carboxylic acid. In each case be sure
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 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 informationChapter 17 Aromati ti S u stit tit t u i tion Reactions
Chapter 17 Aromatic Substitution Reactions 1 17.1 Mechanism for Electricphilic Aromatic Substitution Arenium ion resonance stabilization 2 Example 1. Example 2. 3 Example 2. Mechanism of the nitration
More informationb.p.=100 C b.p.=65 C b.p.=-25 C µ=1.69 D µ=2.0 D µ=1.3 D
Alcohols I eading: Wade chapter 10, sections 10-1- 10-12 Study Problems: 10-35, 10-37, 10-38, 10-39, 10-40, 10-42, 10-43 Key Concepts and Skills: Show how to convert alkenes, alkyl halides, and and carbonyl
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 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 informationCHEMISTRY OF AMINES. There many organic nitrogen containing compounds, among which is amines. Organic nitrogen compounds are:
CHEMISTRY OF AMINES There many organic nitrogen containing compounds, among which is amines. Organic nitrogen compounds are: Amines RNH 2 Amide RCONH 2 Imine R R C=NR Nitrile RC N Generally amines are
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 informationReducing Agents. Linda M. Sweeting 1998
Reducing Agents Linda M. Sweeting 1998 Reduction is defined in chemistry as loss of oxygen, gain of hydrogen or gain of electrons; the gain of electrons enables you to calculate an oxidation state. Hydride
More informationAMINES HYDROXYNITRILES
AMINES ACYL CHLORIDES HYDROXYNITRILES ALDEHYDE/KETONE REDUCTION Amines are nitrogen- containing organic compounds derived from ammonia, where one or more of the hydrogen atoms has been replaced by an alkyl
More informationAromatic Compounds II
2302272 Org Chem II Part I Lecture 2 Aromatic Compounds II Instructor: Dr. Tanatorn Khotavivattana E-mail: tanatorn.k@chula.ac.th Recommended Textbook: Chapter 17 in Organic Chemistry, 8 th Edition, L.
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 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 informationNitro compounds are named by writing the word nitro before the name of the parent compound.
Nitro compounds are an important class of organic compounds which may be regarded as derived from hydrocarbons by the replacement of one or more hydrogen atoms by nitro (NO₂) groups. Nitro arenes(i.e.
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 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 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 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 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 informationCHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Final Exam December 15, 2010 Your name: ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This test contains 15 pages Time: 2h 30 min 1. / 16 2. / 15 3. / 24
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 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 informationQuímica Orgânica I. Ciências Farmacêuticas Bioquímica Química AFB QO I 2007/08 1
Química rgânica I Ciências Farmacêuticas Bioquímica Química AFB Q I 2007/08 1 alcohols Adaptado de rganic Chemistry, 6th Edition; Wade rganic Chemistry, 6 th Edition; McMurry AFB Q I 2007/08 2 Typical
More informationChapter 12. Reactions of Arenes: Electrophilic Aromatic Substitution. Class Notes. A. The method by which substituted benzenes are synthesized
Chapter 12 Reactions of Arenes: Electrophilic Aromatic Substitution Chapter 12 suggested problems: 22, 23, 26, 27, 32, 33 Class Notes I. Electrophilic aromatic substitution reactions A. The method by 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 informationOrganic Chemistry, 7 L. G. Wade, Jr. Chapter , Prentice Hall
Organic Chemistry, 7 th Edition L. G. Wade, Jr. Chapter 17 Reactions of Aromatic Compounds 2010, Prentice Hall Electrophilic Aromatic Substitution Although h benzene s pi electrons are in a stable aromatic
More informationCHEM 345 Problem Set 07 Key
CHEM 345 Problem Set 07 Key 1.) Fill in the appropriate reaction arrow. The starting material is on the left, the product is on the right. Use. Simple Ring Size. 5 and 6 are favored. 3 is not. That s it.
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 informationLecture 15. More Carbonyl Chemistry. Alcohols React with Aldehydes and Ketones in two steps first O R'OH, H + OR" 2R"OH R + H 2 O OR" 3/8/16
Lecture 15 More Carbonyl Chemistry R" R C + R' 2R" R C R" R' + 2 March 8, 2016 Alcohols React with Aldehydes and Ketones in two steps first R', + R R 1 emiacetal reacts further in acid to yield an acetal
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 informationAmmonia and Amines. Four sp 3 hybridized orbitals. Three used for bonding and one for the lone pair of electrons. secondary 2. Et Me.
Ammonia and Amines threefold axis of rotation 111 107 Four sp 3 hybridized orbitals. Three used for bonding and one for the lone pair of electrons. trigonal pyramidal primary 1 secondary 2 tertiary 3 quaternary
More informationORGANIC - CLUTCH CH ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION
!! www.clutchprep.com CONCEPT: ALDEHYDE NOMENCLATURE Replace the suffix of the alkane -e with the suffix On the parent chain, the carbonyl is always terminal, and receive a location As substituents, they
More informationFIVE MEMBERED AROMATIC HETEROCYCLES
FIVE MEMBERED AROMATIC HETEROCYCLES 63 Electrophilic aromatic substitution reaction of five membered aromatic heterocycles X = O, S or NH a-substitution b-substitution The Substitution is regioselective
More informationBenzenes & Aromatic Compounds
Benzenes & Aromatic Compounds 1 Structure of Benzene H H C C C H C 6 H 6 H C C C H H A cyclic conjugate molecule Benzene is a colourless odourless liquid, boiling at 80 o C and melting at 5 o C. It is
More informationCARBONYL COMPOUNDS: OXIDATION-REDUCTION REACTION
CARBONYL COMPOUNDS: OXIDATION-REDUCTION REACTION Introduction Several functional groups contain the carbonyl group Carbonyl groups can be converted into alcohols by various reactions Structure of the Carbonyl
More informationLecture'15:'March'21,'2013
CM'224' 'rganic'chemistry'ii Spring'2013,'Des'Plaines' 'Prof.'Chad'Landrie S C 3 C 3 cimetidine (Tagement) C Lecture'15:'March'21,'2013 Synthesis*of*Amines*(24.1) eac8ons*of*amines**(24.2924.5) Basicity)in)Drug)Development
More informationChapter 19. Synthesis and Reactions of b-dicarbonyl Compounds: More Chemistry of Enolate Anions. ß-dicarbonyl compounds. Why are ß-dicarbonyls useful?
Chapter 19 Synthesis and Reactions of b-dicarbonyl Compounds: More Chemistry of Enolate Anions ß-dicarbonyl compounds Two carbonyl groups separated by a carbon Three common types ß-diketone ß-ketoester
More informationPaper 9: ORGANIC CHEMISTRY-III (Reaction Mechanism-2) Module 16: Reduction by Metal hydrides Part-I
Subject Chemistry Paper No and Title Module No and Title Module Tag 9: ORGANIC -III (Reaction Mechanism-2) 16: Reduction by Metal hydrides Part-I CHE_P9_M16 TABLE OF CONTENTS 1. Learning Outcomes 2. Introduction
More informationEthers can be symmetrical or not:
Chapter 14: Ethers, Epoxides, and Sulfides 175 Physical Properties Ethers can be symmetrical or not: linear or cyclic. Ethers are inert and make excellent solvents for organic reactions. Epoxides are very
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 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 informationORGANIC - EGE 5E CH. 2 - COVALENT BONDING AND CHEMICAL REACTIVITY
!! www.clutchprep.com CONCEPT: HYBRID ORBITAL THEORY The Aufbau Principle states that electrons fill orbitals in order of increasing energy. If carbon has only two unfilled orbitals, why does it like to
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 information