Carboxylic Acids and Carboxylic Acid Deriva3ves. Nucleophilic Acyl Subs0tu0on (Addi0on- Elimina0on)
|
|
- Sharyl Shaw
- 5 years ago
- Views:
Transcription
1 Carboxylic Acids and Carboxylic Acid Deriva3ves Nucleophilic Acyl Subs0tu0on (Addi0on- Elimina0on) 1
2 Carboxylic Compounds Acyl group bonded to X, an electronega3ve atom or leaving group Includes: X = halide (acid halides), acyloxy (anhydrides), alkoxy (esters), amine (amides), thiolate (thioesters), phosphate (acyl phosphates) 2
3 Nomenclature of Carboxylic Acids In systema3c nomenclature, the carbonyl carbon is C- 1. In common nomenclature, the carbon next to the carbonyl is the alpha-carbon. 3
4 Nomenclature of Carboxylic Acids 4
5 Nomenclature of Acyl Halides (Acyl Chlorides and Acyl Bromides) 5
6 Nomenclature of Acid Anhydrides 6
7 Nomenclature of Esters and Carboxylate Ion Salts state the subs3tuent apached to the O delete ic acid add ate 7
8 Nomenclature of Lactones (Cyclic Esters) 8
9 Nomenclature of Amides 9
10 Nomenclature of Lactams (Cyclic Amides) 10
11 Nomenclature of Nitriles 11
12 Physical Proper3es 12
13 Amides and Nitriles Have Rela3vely High Boiling Points 13
14 General Reac3on PaPern Nucleophilic acyl subs3tu3on Why this Chapter? Carboxylic acids (deriva3ves) are among the most widespread of molecules. A study of them and their primary reac3on nucleophilic acyl subs3tu3on is fundamental to understanding organic chemistry 14
15 If the Incoming Nucleophile (Z) is a Weaker Base Than the Base in the Reactant (Y) The weakest base is eliminated from the tetrahedral intermediate. If the incoming nucleophile (Z) is a weaker base than the base in the reactant (Y), the reactants will be reformed. 15
16 If the Incoming Nucleophile (Z) is a Stronger Base Than the Base in the Reactant (Y) The weakest base is eliminated from the tetrahedral intermediate. If the incoming nucleophile (Z) is a stronger base than the base in the reactant (Y), a new product will be formed. 16
17 If the Two Groups Have Similar Basici3es A mixture of reactants and products is obtained. 17
18 Reac3on Coordinate Diagrams 18
19 The Class to which a Carbonyl Group Belongs Depends on the Basicity of the Group APached to the Acyl Group 19
20 The Rela3ve Reac3vi3es Depend on the Basicity of the Subs3tuent APached to the Leaving Group 20
21 Rela3ve Reac3vity of Carboxylic Acid Deriva3ves Nucleophiles react more readily with unhindered carbonyl groups More electrophilic carbonyl groups are more reac3ve to addi3on (acyl halides are most reac3ve, amides are least) The intermediate with the best leaving group decomposes fastest 21
22 Subs3tu3on in Synthesis We can readily convert a more reac3ve acid deriva3ve into a less reac3ve one Reac3ons in the opposite sense are possible but require more complex approaches 22
23 General Reac3ons of Carboxylic Acid Deriva3ves Water is a reagent used to make carboxylic acids Alcohols is a reagent used to make esters ammonia or an amine are used to make an amide hydride source is used to make an aldehyde or an alcohol Grignard reagent is used to make a ketone or an alcohol 23
24 Nucleophilic Acyl Subs3tu3on Reac3ons of Carboxylic Acids Must enhance reac3vity Convert OH into a beper leaving group Specific reagents can produce acid chlorides, anhydrides, esters, amides 24
25 Conversion of Carboxylic Acids into Acid Chlorides Reac3on with thionyl chloride, SOCl 2 25
26 Mechanism of Thionyl Chloride Reac3on Nucleophilic acyl subs3tu3on pathway Carboxylic acid is converted into a chlorosulfite which then reacts with chloride 26
27 Conversion of Carboxylic Acids into Acid Anhydrides Acid anhydrides can be derived from two molecules of carboxylic acid by strong hea3ng to remove water 27
28 Conversion of Carboxylic Acids into Esters Methods include reac3on of a carboxylate anion with a primary alkyl halide 28
29 Fischer Esterifica3on Hea3ng a carboxylic acid in an alcohol solvent containing a small amount of strong acid produces an ester from the alcohol and acid 29
30 Mechanism of the Fischer Esterifica3on The reac3on is an acid- catalyzed, nucleophilic acyl subs3tu3on of a carboxylic acid When 18 O- labeled methanol reacts with benzoic acid, the methyl benzoate produced is 18 O- labeled but the water produced is unlabeled 30
31 Reac3on of a Carboxylic Acid with an Amine A carboxylic acid is an acid and an amine is a base, so an acid- base reac3on occurs. 31
32 Hea3ng the Product of the Acid Base Reac3on Forms an Amide 32
33 Mechanism of Amide Forma3on from Carboxylic Acids 33
34 Dicarboxylic Acids 34
35 The Two pk a Values of Dicarboxylic are Different Why? The neighboring COOH group withdraws electrons and lowers the first pk a. Electrosta3c interac3on between like charges raises the second pk a. 35
36 Dicarboxylic Acids Lose Water When Heated if They Can Form a Five- or Six- Membered Ring 36
37 Ace3c Anhydride (or Acetyl Chloride) Catalyzed Anhydride Forma3on 37
38 Deriva3ves of Carbonic Acid 38
39 Chemistry of Acid Halides Acid chlorides are prepared from carboxylic acids by reac3on with SOCl 2 Reac3on of a carboxylic acid with PBr 3 yields the acid bromide 39
40 Reac3ons of Acid Halides Nucleophilic acyl subs3tu3on Halogen replaced by OH, by OR, or by NH 2 Reduc3on yields a primary alcohol Grignard reagent yields a ter3ary alcohol 40
41 Reac3ons of Acyl Chlorides 41
42 Hydrolysis: Conversion of Acid Halides into Acids Acid chlorides react with water to yield carboxylic acids HCl is generated during the hydrolysis: a base is added to remove the HCl 42
43 Conversion of Acid Halides to Esters Esters are produced in the reac3on of acid chlorides with alcohols in the presence of pyridine or NaOH. This is called Alcoholysis The reac3on is beper with less steric bulk 43
44 Two Equivalents of Amine are Required 44
45 Conversion of Acid Halides into Amides: Aminolysis Amides result from the reac3on of acid chlorides with NH 3, primary (RNH 2 ) and secondary amines (R 2 NH) The reac3on with ter3ary amines (R 3 N) gives an unstable species that cannot be isolated HCl is neutralized by the amine or an added base 45
46 Reduc3on: Conversion of Acid Chlorides into Alcohols LiAlH 4 reduces acid chlorides to yield aldehydes and then primary alcohols 46
47 Reac3on of Acid Chlorides with Organometallic Reagents Grignard reagents react with acid chlorides to yield ter3ary alcohols in which two of the subs3tuents are the same 47
48 Forma3on of Ketones from Acid Chlorides Reac3on of an acid chloride with a lithium diorganocopper (Gilman) reagent, Li + R 2 Cu - Addi3on produces an acyl diorganocopper intermediate, followed by loss of Rʹ Cu and forma3on of the ketone 48
49 Chemistry of Acid Anhydrides Prepared by nucleophilic acyl subs3tu3on of a carboxylate with an acid chloride 49
50 An Acid Anhydride is Formed When Water is Lost from Two Molecules of a Carboxylic Acid 50
51 Reac3ons of Acid Anhydrides 51
52 The Mechanism 52
53 Reac3ons of Acid Anhydrides Similar to acid chlorides in reac3vity 53
54 Acetyla3on Ace3c anhydride forms acetate esters from alcohols and N- subs3tuted acetamides from amines 54
55 Chemistry of Esters Many esters are pleasant- smelling liquids: fragrant odors of fruits and flowers Also present in fats and vegetable oils 55
56 Prepara3on of Esters Esters are usually prepared from carboxylic acids 56
57 Reac3ons of Esters Less reac3ve toward nucleophiles than are acid chlorides or anhydrides Cyclic esters are called lactones and react similarly to acyclic esters 57
58 Hydrolysis: Conversion of Esters into Carboxylic Acids An ester is hydrolyzed by aqueous base or aqueous acid to yield a carboxylic acid plus an alcohol 58
59 Mechanism of Ester Hydrolysis Hydroxide catalysis via an addi3on intermediate 59
60 Aminolysis of Esters Ammonia reacts with esters to form amides 60
61 Reduc3on: Conversion of Esters into Alcohols Reac3on with LiAlH 4 yields primary alcohols 61
62 Mechanism of Reduc3on of Esters Hydride ion adds to the carbonyl group, followed by elimina3on of alkoxide ion to yield an aldehyde Reduc3on of the aldehyde gives the primary alcohol 62
63 Reac3on of Esters with Grignard Reagents React with 2 equivalents of a Grignard reagent to yield a ter3ary alcohol 63
64 Chemistry of Amides Amides are abundant in all living organisms proteins, nucleic acids, and other pharmaceu3cals have amid func3onal groups 64
65 Prepara3on of Amides Prepared by reac3on of an acid chloride with ammonia, monosubs3tuted amines, or disubs3tuted amines 65
66 Reac3ons of Amides Hea3ng in either aqueous acid or aqueous base produces a carboxylic acid and amine Acidic hydrolysis by nucleophilic addi3on of water to the protonated amide, followed by loss of ammonia 66
67 Basic Hydrolysis of Amides Addi3on of hydroxide and loss of amide ion 67
68 Reduc3on: Conversion of Amides into Amines Reduced by LiAlH 4 to an amine rather than an alcohol Converts C=O CH 2 68
69 Mechanism of Reduc3on Addi3on of hydride to carbonyl group Loss of the oxygen as an aluminate anion to give an iminium ion intermediate which is reduced to the amine 69
70 Uses of Reduc3on of Amides Works with cyclic and acyclic Good route to cyclic amines 70
71 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Deriva3ves Nucleophilic carboxyl subs3tu3on in nature ooen involves a thioester or acyl phosphate Acetyl CoA s are most common thioesters in nature 71
72 Polyamides and Polyesters: Step- Growth Polymers Reac3ons occur in dis3nct linear steps, not as chain reac3ons Reac3on of a diamine and a diacid chloride gives an ongoing cycle that produces a polyamide A diol with a diacid leads to a polyester 72
73 Polyamides (Nylons) Hea3ng a diamine with a diacid produces a polyamide called Nylon Nylon 66 is from adipic acid and hexamethylene- diamine at 280 C 73
74 Polyesters The polyester from dimethyl terephthalate and ethylene glycol is called Dacron and Mylar to make fibers 74
75 Synthesis of Nitrile Na CN + R Br RCN + NaBr O R :O: N H H Cl S Cl R O O S N H Cl H B R O O S N H Cl B R C N: O + S + O Cl 75
76 Synthesis of a Carboxylic Acid 76
77 Acid- Catalyzed Hydrolysis of a Nitrile 77
78 The Mechanism 78
79 HYDROLYSIS OF NITRILES TO THE CORRESPONDING CARBOXYLIC ACIDS: The mechanism for the acid-catalyzed conversion of nitriles into carboxylic acids has already been given. However, the use of the base-catalyzed conversion of nitriles into carboxylic acids still does not tolerate the presence of acid-sensitive functional groups because the final step in this sequence is the acid-catalyzed hydrolysis of the primary amide formed by the initial base-catalyzed process. R C N: + OH R C H O H N: R (Why, can it be? It's... C N: it's...it's REGENERATION of the CATALYST!!!!) H :O: H 3 O :O: R OH O H R NH 2 O H H (Can you say, "Tautomerize?") 79
80 Reduc3on of Nitrile R C N: + H R :N: C H 1) H 2) H 3 O H 2 O R NH 2 :O: R H 80
81 Synthesis of Ketone R C N: + R' MgBr R :N: MgBr C R' H 3 O R :O: R' + NH 3 81
Carboxylic Acids. The Importance of Carboxylic Acids (RCO 2 H)
Carboxylic Acids The Importance of Carboxylic Acids (RCO 2 H) Starting materials for acyl derivatives (esters, amides, and acid chlorides) Abundant in nature from oxidation of aldehydes and alcohols in
More informationChapter 10. Carboxylic Acids and Derivatives. Naming Carboxylic Acids and Derivatives. Carboxylic Acids: RCOOH (RCO 2 H)
Chapter 10 Carboxylic Acids and Derivatives Naming Carboxylic Acids and Derivatives Carboxylic Acids: RCH (RC 2 H) The functional group of a carboxylic acid is a carboxyl group (carbonyl & hydroxyl group)
More informationChapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions شیمی آلی 2
Chapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry
More informationChapter 21 The Chemistry of Carboxylic Acid Deriva7ves
Organic Chemistry, 5th ed. Marc Loudon Chapter 21 The Chemistry of Carboxylic Acid Deriva7ves Eric J. Kantorowski California Polytechnic State University San Luis Obispo, CA Chapter 21 Overview 21.1 Nomenclature
More informationCarboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions Dr. Ayad Kareem Department of Pharmaceutical Chemistry, Collage of Pharmacy Al-Mustansiriyah University (2017-2018). Closely related
More informationCARBOXYLIC ACIDS AND THEIR DERIVATIVES: NUCLEOPHILIC ADDITION-ELIMINATION AT THE ACYL CARBON
CARBOXYLIC ACIDS AND THEIR DERIVATIVES: NUCLEOPHILIC ADDITION-ELIMINATION AT THE ACYL CARBON RED ANT WAS SOURCE OF FORMIC ACID (RCOOH) Lecture 8 ORGANIC CHEMISTRY 2 Introduction The carboxyl group (-CO
More informationCh 21 Carboxylic Acid Derivatives and Nu Acyl Subst n
Ch 21 Carboxylic Acid Derivatives and Nu Acyl Subst n Acid Derivatives and their Names - Acid Halides have a Cl or Br instead of OH. Replace ic acid with yl halide, such as propionyl chloride (a common
More informationChapter 18. Carboxylic Acids and Their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon
Chapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon Carboxylic Acids Organic compounds characterized by their acidity Contains COOH group (must be at
More informationChapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic Addition- Elimination at the Acyl Carbon
Chapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic Addition- Elimination at the Acyl Carbon Introduction The carboxyl group (-CO 2 H) is the parent group of a family of compounds called acyl
More informationR O R' Acid anhydride. Acid halide. Carboxylic acid. Ester O O O O. Nitrile Acyl phosphate Thioester. Amide
Chapter 10. Carboxylic Acids and Derivatives Carboxylic acid X Acid halide ' Acid anhydride Ester ' P N 2 C N S' Amide Nitrile Acyl phosphate Thioester The common structural feature of all these compounds
More information1/3/2011. Chapter 17 Carboxylic Acids and Their Derivatives. Nucleophilic Addition- Elimination at the Acyl Carbon
Introduction The carboxyl group (-CO 2 H) is the parent group of a family of compounds called acyl compounds or carboxylic acid derivatives Chapter 17 Carboxylic Acids and Their Derivatives. Nucleophilic
More informationCarboxylic Acids and Nitriles. Chapters 20, 21 Organic Chemistry, 8th Edition John McMurry
Carboxylic Acids and Nitriles Chapters 20, 21 Organic Chemistry, 8th Edition John McMurry 1 Carboxylic Acid Derivatives 2 Carboxylic Acid Derivatives nitrile R = CH 3 acetonitrile 3 Structure and Bonding
More informationCarboxylic Acid Derivatives Reading Study Problems Key Concepts and Skills Lecture Topics: Structures and reactivity of carboxylic acid derivatives
Carboxylic Acid Derivatives Reading: Wade chapter 21, sections 21-1- 21-16 Study Problems: 21-45, 21-46, 21-48, 21-49, 21-50, 21-53, 21-56, 21-58, 21-63 Key Concepts and Skills: Interpret the spectra of
More informationFundamentals of Organic Chemistry CHEM 109 For Students of Health Colleges Credit hrs.: (2+1)
Fundamentals of Organic Chemistry CHEM 109 For Students of Health Colleges Credit hrs.: (2+1) King Saud University College of Science, Chemistry Department CHEM 109 CHAPTER 7. CARBOXYLIC ACIDS AND THEIR
More informationEsters of Carboxylic Acids These are derivatives of carboxylic acids where the hydroxyl group is replaced by an alkoxy group.
Carboxylic acid Derivatives Carboxylic acid derivatives are described as compounds that can be converted to carboxylic acids via simple acidic or basic hydrolysis. The most important acid derivatives are
More informationDERIVATIVES OF CARBOXYLIC ACIDS
13 Rl RH RNH 2 RR RR DERIVATIVES F ARBXYLI AIDS HAPTER SUMMARY 13.1 Structure and Nomenclature of arboxylic Acid Derivatives A. Structure arboxylic acids and their derivatives can be expressed as variations
More information10. CARBOXYLIC ACIDS AND THEIR DERIVATIVES 10.1 Nomenclature of Carboxylic Acids 10.2 Physical Properties of Carboxylic Acids 10.
BOOKS 1) Organic Chemistry Structure and Function, K. Peter C. Vollhardt, Neil Schore, 6th Edition 2) Organic Chemistry, T. W. Graham Solomons, Craig B. Fryhle 3) Organic Chemistry: A Short Course, H.
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 informationLoudon Chapter 21 Review: Carboxylic Acid Derivatives Jacquie Richardson, CU Boulder Last updated 3/20/2018
Loudon Chapter 21 eview: Carboxylic Acid Derivatives Jacquie ichardson, CU Boulder Last updated 3/20/2018 We learned how to make a lot of carboxylic acid derivatives from acids in Ch. 20, but now we ll
More informationCarboxylic Acids and Their Derivatives. Chapter 17. Carboxylic Acids and Their Derivatives
Chapter 17 Carboxylic Acids and Their Derivatives Chapter 17 suggested problems: 36, 38, 40, 42, 44, 52, 54, 56, 62, 64, 66, 70 Class Notes I. Carboxylic acids (organic acids) and their derivatives A.
More informationChapter 20: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
hapter 20: arboxylic Acid Derivatives: ucleophilic Acyl Substitution 20.1: omenclature of arboxylic Acid Derivatives (please read) carboxylic acid -oic acid ' ester -oate ' lactone cyclic ester l acid
More informationChapter 21. Carboxylic Acid Derivatives. and Nucleophilic Acyl Substitution. Reactions. - many carboxylic acid derivatives are known:
hapter 21 arboxylic Acid Derivatives and ucleophilic Acyl Substitution eactions - many carboxylic acid derivatives are known: X ' carboxylic acid acid halide (X = F, l, Br, I) acid anhydride ' 2 ester
More informationCarboxylic acid derivatives
Carboxylic acid derivatives Nucleophilic acyl substitution reaction Among the most important reactions of carboxylic acids are those that convert the carboxyl group into other acid derivatives by a nucleophilic
More informationAlehydes, Ketones and Carboxylic Acid
Alehydes, Ketones and Carboxylic Acid Aldehydes and Ketones: Introduction Aldedydes and ketones are organic compounds that contain carbon-oxygen doule bonds. The general formula for aldehydes is O C R
More informationChapter 17 Carboxylic Acids, Esters, and Amides Prepared by Andrea D. Leonard University of Louisiana at Lafayette
Chapter 17 Carboxylic Acids, Esters, and Amides Prepared by Andrea D. Leonard University of Louisiana at Lafayette Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
More informationCarboxylic Acids and their Derivatives I
2302272 Org Chem II Part I Lecture 5 Carboxylic Acids and their Derivatives I Instructor: Dr. Tanatorn Khotavivattana E-mail: tanatorn.k@chula.ac.th Recommended Textbook: Chapter 20 in Organic Chemistry,
More informationChapter 20 Carboxylic Acids. Introduction
hapter 20 arboxylic Acids Introduction arbonyl (-=) and hydroxyl (-H) on the same carbon is carboxyl group. arboxyl group is usually written -H or 2 H. Aliphatic acids have an alkyl group bonded to -H.
More informationChapter 19: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution 19.1: Nomenclature of Carboxylic Acid Derivatives (please read)
problem 18.33b - = 128.7 123.9 179.7 146.8 147.4 45.3 18.0 161 hapter 19: arboxylic Acid Derivatives: ucleophilic Acyl Substitution 19.1: omenclature of arboxylic Acid Derivatives (please read) carboxylic
More informationLecture 19. Nucleophilic Acyl Substitution Y - + X - Y X R C X. April 2, Chemistry 328N
Lecture 19 Nucleophilic Acyl Substitution X Y - - Y X X - Y April 2, 2019 hemistry 328N Acid-catalyzed Esterification (also called Fischer esterification) H H 3 H H H 2 H 3 Please study the mechanism hemistry
More informationLecture 20. Herman Emil Fischer Nobel Prize 1902 Sugars, Esters and Purines. April 4, Chemistry 328N
Lecture 20 April 4, 2019 Herman Emil Fischer 1852-1919 Nobel Prize 1902 Sugars, Esters and Purines Acid-catalyzed Esterification (also called Fischer esterification) CH CH 3 H H H 2 CCH 3 Please study
More informationPhysical properties: C L = L. Cl, NH 2, OCH 3, OH, OCR O O O NH 2 CH 3 N(CH 3 ) 2. Sol. in H 2 O
Lecture Notes hem 51 S. King hapter 22 arboxylic Acids and their Derivatives: Nucleophilic Acyl Substitution I. Structure and Physical Properties: Type 2 carbonyl compounds (carboxylic acids and derivatives)
More informationChemistry Chapter 19
hemistry 2100 hapter 19 arboxyl Derivatives In this chapter, we study three classes of compounds derived from carboxylic acids; anhydrides, esters, and amides. Each is related to a carboxyl group by loss
More informationCarboxylic Acid Derivatives: Nucleophilic Acyl Substitution
Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Carboxylic Acid Derivatives Carboxylic acid derivatives. Acyl chloride Acid anhydride Ester Amide Nucleophilic acyl substitution 19.1 Nomenclature
More informationEXPERIMENT 8 (Organic Chemistry II) Carboxylic Acids Reactions and Derivatives
EXPERIMENT 8 (rganic Chemistry II) Carboxylic Acids Reactions and Derivatives Pahlavan/Cherif Materials Medium test tubes (6) Test tube rack Beakers (50, 150, 400 ml) Ice Hot plate Graduated cylinders
More informationFunctional Derivatives of Carboxylic Acids
Functional Derivatives of Carboxylic Acids Derivatives of Carboxylic Acids are compounds in which the OH of a carboxyl group has been replaced by CI, OOCR, NH2, or OR'to convert acid chlorides,anhydrides,
More informationPaper 9: ORGANIC CHEMISTRY-III (Reaction Mechanism-2) Module17: Reduction by Metal hydrides Part-II CHEMISTRY
Subject Chemistry Paper No and Title Module No and Title Module Tag 9: ORGANIC -III (Reaction Mechanism-2) 17: Reduction by Metal hydrides Part-1I CHE_P9_M17 Table of Contents 1. Learning Outcomes 2. Introduction
More informationCarboxylic Acid Derivatives
arboxylic Acid Derivatives The most important derivatives of carboxylic acids are l " ' ' acid halide acid anhydride an ester an amide Although not direct derivatives, nitriles, -, are related to carboxylic
More informationREACTIONS OF CARBOXYLIC ACID DERIVATIVES WITH NUCLEOPHILES A. Reactions of Acid Chlorides with Nucleophiles
1016 CHAPTER 1 THE CHEMITRY F CARBXYLIC ACID DERIVATIVE 1.8 REACTI F CARBXYLIC ACID DERIVATIVE WITH UCLEPHILE ection 1.7 showed that all carboxylic acid derivatives hydrolyze to carboxylic acids. Water
More informationCh. 21: CARBOXYLIC ACID DERIVATIVES AND NUCLEOPHILIC ACYL SUBSTITUTION REACTIONS Nomenclature of Carboxylic Acid Derivatives:
h. 21: ABXYLI AID DEIVATIVES AND NULEPILI AYL SUBSTITUTIN EATINS Nomenclature of arboxylic Acid Derivatives: arboxylic acids "-oic acid" Examples: 3 2 Propanoic acid yclohexanecarboxylic acid 1 arboxylate
More informationA. Carboxylic acid functional groups contain the carboxyl structural feature. 1. Features of the carboxyl group
Chapter 17 Carboxylic Acids and Their Derivatives Chem 306 Roper I. Overview A. Carboxylic acid functional groups contain the carboxyl structural feature. 1. Features of the carboxyl group 2. The reactivity
More informationCH 3 C H 3 O. anhydride acid. ester amide. O acid O. amide. acid. amide. acid. nitriles
C 21: Carboxylic Acid Derivatives Topics: aming Interconversion of Acid Derivatives eactions of each functional group Connections: anhydride acid ester amide acid ester amide acid amide 2 acid nitriles
More informationChapters 13/14: Carboxylic Acids and Carboxylic Acid Derivatives
CHM 201 (Elements of Organic Chemistry) Dr. Virgil Lee Cal Poly Pomona Chapters 13/14: Carboxylic Acids and Carboxylic Acid Derivatives resonance stabilized OH group donates electron density to carbonyl
More informationPrelab 6: Carboxylic Acids
The Structure of Carboxylic Acids Prelab 6: Carboxylic Acids Carboxylic acids contain a carboxyl functional group attached to a hydrocarbon (alkyl group) part. Carboxyl groups contain both a carbonyl group,
More informationLecture'11:'February'21,'2013 Reac&ons*of*Deriva&ves*( )
CM'224' 'rganic'chemistry'ii Spring'2013,'Des'Plaines' 'Prof.'Chad'Landrie Vegetable il (C 2 ) 7 (C 2 ) 7 (C 2 ) 7 LL (a triacylglyceride in soybean oil) (1) transesterification ac 3 Biodiesel 3 C 3 C
More informationCarboxylic Acids, Esters and Acyl Chlorides
R hemistry A 432 arboxylic Acids, Esters and Acyl hlorides arboxylic Acids, Esters and Acyl hlorides arboxylic acids contain the functional group, attached to an alkyl stem. They are widely found in nature,
More informationNu: - Addition or Nu: - Acyl Substitution?
12. Apply nucleophilic addition and elimination concepts to nucleophilic acyl substution reactions of acids and derivatives (focus on esters and amides) In Class problems: 1. The reactive site of aldehydes,
More informationCarboxylic Acids and Esters
24 Carboxylic Acids and Esters The sour tang in fruit juice comes from carboxylic acids. Introduction to General, Organic, and Biochemistry, 10e John Wiley & Sons, Inc Morris Hein, Scott Pattison, and
More informationChapter 15. Alcohols, Diols, and Thiols. B. Sources: there are two principal sources of simple aliphatic alcohols
Chapter 15 Alcohols, Diols, and Thiols Chapter 15 suggested problems: 17, 19, 24, 28, 37, 39 I. Introduction A. The relevance of alcohols (from M&B: 497): "If an organic chemist were allowed to choose
More informationORGANIC SYNTHESIS VIA ENOLATES
1 ORGANIC SYNTHESIS VIA ENOLATES Aldehydes and ketones undergo nucleophilic addition reaction at the carbonyl group. Further, α-hydrogen containing compounds are acidic in nature. In addition to carbonyl
More informationChapter 7- Alkenes: Structure and Reactivity. Ashley Piekarski, Ph.D. Alkene
Chapter 7- Alkenes: Structure and Reactivity Ashley Piekarski, Ph.D. Alkene What is an alkene func
More informationIdentifying Functional Groups. (Chapter 2 in the Klein text)
Identifying Functional Groups (Chapter 2 in the Klein text) Basic Ideas A functional group is a substructure within a molecule that will have the potential to undergo chemical change, i.e. the group has
More informationEsterification. Preparation of β-d-glucose pentaacetate. Dr. Zerong Wang at UHCL. Table of contents
Esterification Preparation of β-d-glucose pentaacetate Table of contents Ester eaction with carboxylic acids eaction with esters: transesterification eaction with acid anhydrides eaction with acid halides
More informationThis is an addition reaction. (Other types of reaction have been substitution and elimination). Addition reactions are typically exothermic.
Reactions of Alkenes Since bonds are stronger than bonds, double bonds tend to react to convert the double bond into bonds + X-Y X Y This is an addition reaction. (Other types of reaction have been substitution
More informationLecture Notes Chemistry Mukund P. Sibi Lecture 31 Reactions at the Alpha-Carbon of Carbonyl Compounds
Lecture Notes hemistry 342-2008 Mukund P. Sibi eactions at the Alpha-arbon of arbonyl ompounds Enolates are nucleophilic and undergo reaction with electrophiles. For example, one can do halogenation under
More information13. Carboxylic Acids (text )
2009, Department of Chemistry, The University of Western ntario 13.1 13. Carboxylic Acids (text 14.1 14.9) A. Structure and Nomenclature The carboxylic acid functional group results from the connection
More informationH O. rapidly reduces. They dissolve. because they can hydrogen bond to the water molecules.
3.9 arboxylic Acids and Derivatives Naming arboxylic acids These have the ending oic acid but no number is necessary for the acid group as it must always be at the end of the chain. The numbering always
More informationChem 263 Nov 26, 2013 O R' alkyl. acid. ethyl. acetic acid. ethyl acetate ethyl ethanoate
hem 263 ov 26, 2013 arboxylic Acids and Derivatives omenclature Esters Systematic names for esters are derived by first giving the name of the alkyl group attached to the oxygen, and then identifying the
More informationCarboxylic Acids and Their Derivatives
arboxylic Acids and Their Derivatives Families ontaining the arbonyl Group Family Y Z Y Z aldehyde or ketone carboxylic acid or -- ester or -- acid halide or -F,-l,-Br,-I acid anhydride or amide or -N
More informationCarbonyl Chemistry VI + C O C. 1pm In Geology Room 112. Exam is Monday 11am-1pm. Chemistry /06/02
arbonyl hemistry VI Ō - + hemistry 391 11/06/02 Exam is Monday 11am-1pm 1pm In Geology Room 112 The Dibasic Acids h - My - Such - hemistry 391 11/06/02 Good- Apple- Pie- Fischer Esterification Esters can
More informationChapter 16 and GHW#6 Questions. Carboxylic Acids, Esters, and Other Acid Derivatives
Chapter 16 and GHW#6 Questions Carboxylic Acids, Esters, and Other Acid Derivatives Bonding Characteristics of Carboxylic Acids A carboxylic acid has functional a carboxyl group. A carboxyl group is a
More informationChap 7: Alcohols, Phenols, & Thiols
Chap 7: Alcohols, Phenols, & Thiols Objectives: Chap 7: Alcohols, Phenols, & Thiols (Chapter 7 and pages 283-285 & 296-297, A-1 & A-2 in lab manual) 1. Identify molecules as an alcohol, phenol, glycol,
More informationCarboxylic Acids. Carboxylic acid groups are always terminal groups with a carbonyl carbon also bound to a hydroxyl For example:
Carboxylic Acids The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. Structure of Carboxyl Carbon is sp 2 hybridized. Bond angles are close to 120. O-H eclipsed
More information22. The Fischer Esterification
22. The Fischer Esterification A. Background Esters are an incredibly important functional group in organic chemistry. Esters are typically very pleasant smelling molecules and are therefore frequently
More information3/27/2011. Chapter 8 Reactions of Alkenes and Alkynes. Alkene Addition Reactions. 8.1 Preparing Alkenes: A Preview of Elimination Reactions
John E. McMurry http://www.cengage.com/chemistry/mcmurry Chapter 8 Reactions of Alkenes and Alkynes Richard Morrison University of Georgia, Athens Alkene Addition Reactions Alkene addition reactions Addition
More informationCarboxylic Acids and Esters
arboxylic Acids and Esters N Goalby hemrevise.org - absorption IR Spectrum for arboxylic acids Butanoic acid 1 Solubility in Water The smaller carboxylic (up to 4) acids dissolve in water in all proportions
More informationChem 263 B6 Notes March 30, 2006 Demo-In-Class: O
hem 263 B6 otes March 30, 2006 Demo-In-lass: + 2 carbon dioxide carbonic acid arbon dioxide ( 2 ) is a solid at -78. It is dry ice. When it is added to water, we made carbonated water (as in soda pop).
More information6/9/2015. Unit 15: Organic Chemistry Lesson 15.2: Substituted Hydrocarbons & Functional Groups
1-chloropropane 2-methylpropane 1-iodobutane Ethanoic Acid Unit 15: Organic Chemistry Lesson 15.2: Substituted Hydrocarbons & Functional Groups 43 It Ain t Just Hydrocarbons There are all sorts of organic
More information(iii). Decarboxylation (iv)kolbe Electrolysis
ALKANOIC ACID/CARBOXYLIC ACID Contains carboxyl functional group COOH Two functional groups are contained in carboxyl- carbonyl (C=O)and hydroxyl (-OH) Saturated aliphatic alkanoic acids have general formula
More informationChemistry 1120 Exam 1 Study Guide
Chemistry 1120 Exam 1 Study Guide Chapter 3 3.1 a) Know that alcohols contain a hydroxy (-OH) group. Determine the IUPAC name for a given structure by determining the longest chain. b) Determine the number
More informationH 3 C OCH 3 3 C N(CH 3 ) 2 H 3 C H H 3 C CH 3. ketone. pk a = 9 H H. 1,3-keto ester pk a = 11
hapter 21: Ester Enolates 21.1: Ester α ydrogens and Their pk a s. The α-protons of s are less acidic that ketones and aldehydes. Typical pk a s of carbonyl compounds (α-protons): aldehydes 17 ketones
More informationAlcohol aldehydes cetones and carboxylic acids
Alcohol aldehydes cetones and carboxylic acids 1 Classes of organic compounds 2 Alcohols Alcohols are organic compounds containing hydroxyl (-OH) group attached to C atom. In an alcohol, -OH group replaces
More informationREVIEW IN CARBOXYLIC ACIDS AND ITS DERIVATIVES
IASET: International Journal of Agricultural & Bio-Chemical Science (IASET: IJABS) ISSN(P): Applied; ISSN(E): Applied Vol. 1, Issue 1, Jan - Jun 2017, 49-66 IASET REVIEW IN CARBXYLIC ACIDS AND ITS DERIVATIVES
More informationTOPIC 4. CARBOXYLIC ACIDS AND THEIR DERIVATES: NUCLEOPHILIC ADDITION-ELIMINATION AT THE ACYL CARBON (Chapter 17)
L TPI 4. ABXYLI AIDS AND TEI DEIVATES: NULEPILI ADDITIN-ELIMINATIN AT TE AYL ABN (hapter 17) BJETIVES 1. Name carboxylic acids and acid derivatives: acyl chlorides, anhydrides, esters, amides and nitriles
More information3.12 Polymers. As with esters, the OH from the carboxylic acid is lost with the H from the alcohol.
3.12 s Condensation polymerisation: This is the joining of 2 monomers while eliminating a small molecule - H 2 O or HCl The functional group on one monomer joins with a different functional group in another
More informationSolution CHEMISTRY (B) (CH3O)2CH COOH & HCHO. (A) Sulphur (B) Phosphorus (C) Magnesium (D) Chlorine
CHEMISTRY 31. H H OH H OH H OH H OCH 3 OCH 3 A & B are HIO 4 A B ( 2H2O) (A) HCHO & HCOCH(OCH3)2 (C) (CH3O)2C = O and COOH COOH (B) (CH3O)2CH COOH & HCHO (D) HCOOH & HCOCH(OCH3)2 32. In vulcanization of
More informationChem 263 Nov 21, 2013
hem 263 Nov 21, 2013 arbohydrates- emiacetal Formation You know from previous lectures that carbonyl compounds react with all kinds of nucleophiles. ydration and hemiacetal formation are typical examples.
More informationChemistry 212 Fall Semester 1996 Examination #2
Chemistry 212 Fall Semester 1996 Examination #2 University of Missouri Columbia Prof. Rainer Glaser Wednesday, October 16, 1996 103 Schlundt Hall, 8:40-9:30 featuring Carboxylic Acids and Carboxylic Acid
More informationDiverse Reactions of Alkenes
Chapter 8- Alkenes: Reactions and Synthesis Ashley Piekarski, Ph.D. Diverse Reactions of Alkenes Alkenes react with many electrophiles to give useful products by addiaon (ocen through special reagents)
More informationEsters An Introduction To Organic Chemistry Reactions
We have made it easy for you to find a PDF Ebooks without any digging. And by having access to our ebooks online or by storing it on your computer, you have convenient answers with esters an introduction
More informationMacromolecules. Small molecules that join together to form one large polymer molecules.
Macromolecules Polymerisation: Polymerisation is the joining of small molecules (monomers), into chains of a very large molecule (polymer). The monomers can be as atoms, simple molecules of ethen as in
More informationCELLULAR METABOLISM. Metabolic pathways can be linear, branched, cyclic or spiral
CHM333 LECTURE 24 & 25: 3/27 29/13 SPRING 2013 Professor Christine Hrycyna CELLULAR METABOLISM What is metabolism? - How cells acquire, transform, store and use energy - Study reactions in a cell and how
More informationChem 263 Dec 1, 2016
Chem 263 Dec 1, 2016 eactivity of Carboxylic acid Derivatives More eactive S 2 ' ' + a ' 2 - M + Less eactive Example: Acid chloride to anhydride Since an acid chloride is more reactive than an anhydride,
More informationFundamentals of Organic Chemistry CHEM 109 For Students of Health Colleges
Fundamentals of Organic Chemistry CHEM 109 For Students of Health Colleges Credit hrs.: (2+1) King Saud University College of Science, Chemistry Department CHEM 109 CHAPTER 9. AMINO ACIDS, PEPTIDES AND
More informationBIOLOGICAL MOLECULES REVIEW-UNIT 1 1. The factor being tested in an experiment is the A. data. B. variable. C. conclusion. D. observation. 2.
BIOLOGICAL MOLECULES REVIEW-UNIT 1 1. The factor being tested in an experiment is the A. data. B. variable. C. conclusion. D. observation. 2. A possible explanation for an event that occurs in nature is
More informationHydrolytic transformations involving amide-, ester bonds are the easiest to perform
Hydrolytic reactions Hydrolytic transformations involving amide-, ester bonds are the easiest to perform Proteins used for these reactions are proteases, esterases or lipases. A favourite class of enzymes
More informationESTERS AND RELATED CARBOXYLIC ACID DERIVATIVES. Jack DeRuiter
ESTES AD ELATED ABYLI AID DEIVATIVES I. Structure and Preparation Jack Deuiter Esters are derivatives of carboxylic acids that arise via replacement of the hydroxyl () portion of the acid function with
More informationChemistry B11 Chapters 13 Esters, amides and carbohydrates
Chapters 13 Esters, amides and carbohydrates Esters: esters are derived from carboxylic acids (the hydrogen atom in the carboxyl group of carboxylic acid is replaced by an alkyl group). The functional
More informationChapter 8 Lecture Reactions of Alkenes
Organic Chemistry, 9 th Edition L. G. Wade, Jr. Chapter 8 Lecture Reactions of Alkenes 2017 Pearson Education, Inc. Catalytic Hydrogenation of Alkenes Hydrogen (H 2 ) can be added across the double bond
More informationAlkenes are very useful in syntheses -they allow us to convert into many of the other types of functional groups.
Chapter 7: Alkenes: reactions and synthesis Alkenes are very useful in syntheses -they allow us to convert into many of the other types of functional groups. 7.1 Preparation of alkenes: preview Addition
More informationChemicals Based on Ethylene
Chemicals Based on Ethylene Ethylene is sometimes known as the king of petrochemicals because more commercial chemicals are produced from ethylene than from any other intermediate. This unique position
More informationThe Rules for Boiling Points
The Rules for Boiling Points The boiling points of compounds depend on how strongly they stick together: The more strongly they stick together, the higher the boiling point (the more heat it takes to rip
More informationMITOCW watch?v=xms9dyhqhi0
MITOCW watch?v=xms9dyhqhi0 The following content is provided under a Creative Commons license. Your support will help MIT OpenCourseWare continue to offer high-quality, educational resources for free.
More informationTopic 4.5 COMPOUNDS CONTAINING THE CARBONYL GROUP. Aldehydes and Ketones Carboxylic Acids and their Salts Esters Acyl Chlorides and Acid Anhydrides
Topic 4.5 MPUNDS NTAINING TE ARBNYL GRUP Aldehydes and Ketones arboxylic Acids and their Salts Esters Acyl hlorides and Acid Anhydrides ALDEYDES AND KETNES 1. Introduction Aldehydes and ketones are collectively
More information11/5/ Oxidation of Alkenes: Cleavage to Carbonyl Compounds. Oxidation of Alkenes: Cleavage to Carbonyl Compounds
8.8 Oxidation of Alkenes: Cleavage to Carbonyl Compounds Ozone (O 3 ) is useful double-bond cleavage reagent Ozone is generated by passing a stream of oxygen through a highvoltage electrical discharge
More informationCarboxylic Acids. Seminar_7
Seminar_7 1. Nomenclature of Carboxylic Acids 2. Preparation of Carboxylic Acids 3. Reactivity 4. Soaps and Detergents 5. Fats and Oils TEST Carboxylic acides, esters and fats. Give the names Carboxylic
More informationAS Describe aspects of organic chemistry. COLLATED POLYMER QUESTIONS - polyesters, polyamides and peptides
o Brain Too Small EMISTRY AS 90698 Describe aspects of organic chemistry LLATED PLYMER QUESTIS - polyesters, polyamides and peptides (2011:2) ylon 6,6 is a polymer with the following structure: (a) (b)
More informationChapter 15 Alcohols, Diols, and Thiols
Chapter 15 Alcohols, Diols, and Thiols 15.1 Sources of Alcohols Methanol Methanol is an industrial chemical end uses: solvent, antifreeze, fuel principal use: preparation of formaldehyde Methanol Methanol
More informationName the ester produced when methanol and pentanoic acid react. methyl pentanoate. Name the type of reaction used to make an ester
1 Name the ester produced when methanol and pentanoic acid react methyl pentanoate 2 Name the type of reaction used to make an ester condensation reaction 3 Name the by-product of the reaction used to
More informationCh14. Carboxylic Acids. Combining the hydroxyl and carbonyl functional groups. To make more powerful functional groups. version 1.
Ch14 Carboxylic Acids Combining the hydroxyl and carbonyl functional groups. To make more powerful functional groups. version 1.0 Nick DeMello, PhD. 2007-2015 Ch14 Carboxylic Acids & Esters Carboxylic
More information