Química Orgânica I. Ciências Farmacêuticas Bioquímica Química AFB QO I 2007/08 1
|
|
|
- Loraine Carroll
- 5 years ago
- Views:
Transcription
1 Química rgânica I Ciências Farmacêuticas Bioquímica Química AFB Q I 2007/08 1
2 alcohols Adaptado de rganic Chemistry, 6th Edition; Wade rganic Chemistry, 6 th Edition; McMurry AFB Q I 2007/08 2
3 Typical reactions of alcohols Two general classes of reaction At the carbon of the C bond At the proton of the H bond AFB Q I 2007/08 3
4 Types of Alcohol Reactions Dehydration to alkene xidation to aldehyde, ketone Substitution to form alkyl halide Reduction to alkane Esterification Tosylation Williamson synthesis of ether => AFB Q I 2007/08 4
5 Summary Table AFB Q I 2007/08 5 =>
6 xidation States Easy for inorganic salts Cr 4 2- reduced to Cr 2 3 KMn 4 reduced to Mn 2 xidation: loss of H 2, gain of, 2, or X 2 Reduction: gain of H 2 or H-, loss of, 2, or X 2 Neither: gain or loss of H +, H 2, HX => AFB Q I 2007/08 6
7 xydation 1º Carbons 2º Carbons 3º Carbons AFB Q I 2007/08 7 =>
8 xidation of 1 Alcohols 1 alcohol to aldehyde to carboxylic acid Difficult to stop at aldehyde Use pyridinium chlorochromate (PCC) to limit the oxidation. PCC can also be used to oxidize 2 alcohols to ketones. H N H Cr 3 Cl CH 2 CH 2 CH 2 CH 2 CH 2 CH AFB Q I 2007/08 8 =>
9 xidation of 2 Alcohols 2 alcohol becomes a ketone Reagent is Na 2 Cr 2 7 /H 2 S 4 Active reagent probably H 2 Cr 4 Color change: orange to greenishblue H CHCH 2 Na 2 Cr 2 7 / H 2 S 4 CCH 2 => AFB Q I 2007/08 9
10 Mechanism of Chromic Acid xidation Alcohol forms a chromate ester followed by elimination with electron transfer to give ketone AFB Q I 2007/08 10
11 3 Alcohols Don t xidize Cannot lose 2 H s Basis for chromic acid test => AFB Q I 2007/08 11
12 ther xidation Reagents Collins reagent: Cr 2 3 in pyridine Jones reagent: chromic acid in acetone KMn 4 (strong oxidizer) Nitric acid (strong oxidizer) Cu, 300 C (industrial dehydrogenation) Swern oxidation: dimethylsulfoxide, with oxalyl chloride and hindered base, oxidizes 2 alcohols to ketones and 1 alcohols to aldehydes. => AFB Q I 2007/08 12
13 xidation of Primary Alcohols with K Cr (Jones) K 2 Cr 2 7 K 2 Cr 2 7 R CH 2 H R C H R C H H 2 S 4 H 2 S 4 + Cr 3+ Jones xidation
14 xidation with Chromic xide and Pyridine H R CH R Cr 3. CH 2 Cl 2 N R C R Sarrett reaction: Primary alcohols get oxidized to aldehydes Aldehydes are not further oxidized to carboxylic acids Sarett xidation
15 The Swern xidation AFB Q I 2007/08 15
16 Mechanism of the Swern xidation AFB Q I 2007/08 16
17 The Tollens Reagent xidizes nly Aldehydes AFB Q I 2007/08 17
18 Both aldehydes and ketones can be oxidized by peroxyacid: The Baeyer Villiger oxidation AFB Q I 2007/08 18
19 AFB Q I 2007/08 19
20 Mechanism of the Baeyer Villiger xidation AFB Q I 2007/08 20
21 Therefore, the product of the Baeyer Villiger oxidation of cyclohexyl methyl ketone will be cyclohexyl acetate, because a secondary alkyl group is more likely to migrate than AFB a methyl group Q I 2007/08 21
22 Biological xidation Catalyzed by ADH, alcohol dehydrogenase. xidizing agent is NAD +, nicotinamide adenine dinucleotide. Ethanol oxidizes to acetaldehyde, then acetic acid, a normal metabolite. Methanol oxidizes to formaldehyde, then formic acid, more toxic than methanol. Ethylene glycol oxidizes to oxalic acid, toxic. Treatment for poisoning is excess ethanol. AFB Q I 2007/08 22 =>
23 Biological xidation Reduction Reactions AFB Q I 2007/08 23
24 AFB Q I 2007/08 24
25 NAD + oxidizes ethanol by accepting a hydride ion AFB Q I 2007/08 25
26 NADH reduces a carbonyl compound by donating a hydride ion AFB Q I 2007/08 26
27 Alcohol as a Nucleophile H C R X RH is weak nucleophile R - is strong nucleophile New -C bond forms, -H bond breaks. => AFB Q I 2007/08 27
28 Alcohol as an Electrophile H - is not a good leaving group unless it is protonated, but most nucleophiles are strong bases which would remove H +. + C H Convert to tosylate (good leaving group) to react with strong nucleophile (base) C-Nuc bond forms, C- bond breaks => AFB Q I 2007/08 28
29 Formation of Tosylate Ester C H Cl S N H C S C S p-toluenesulfonyl chloride TsCl, tosyl chloride RTs, a tosylate ester => AFB Q I 2007/08 29
30 S N 2 Reactions of Tosylates With hydroxide produces alcohol With cyanide produces nitrile With halide ion produces alkyl halide With alkoxide ion produces ether With ammonia produces amine salt With LiAlH 4 produces alkane => AFB Q I 2007/08 30
31 Summary of Tosylate Reactions => AFB Q I 2007/08 31
32 Reduction of Alcohols Dehydrate with conc. H 2 S 4, then add H 2 Tosylate, then reduce with LiAlH 4 H H 2 S 4 H 2 CH CH 2 CH CH 2 Pt alcohol alkene alkane H CH alcohol TsCl Ts CH tosylate LiAlH 4 CH 2 alkane => AFB Q I 2007/08 32
33 Reaction with HBr -H of alcohol is protonated -H 2+ is good leaving group 3 and 2 alcohols react with Br - via S N 1 1 alcohols react via S N 2 H 3 + H Br - R H R H R Br => AFB Q I 2007/08 33
34 Reaction with HCl Chloride is a weaker nucleophile than bromide. Add ZnCl 2, which bonds strongly with -H, to promote the reaction. The chloride product is insoluble. Lucas test: ZnCl 2 in conc. HCl 1 alcohols react slowly or not at all. 2 alcohols react in 1-5 minutes. 3 alcohols react in less than 1 minute. => AFB Q I 2007/08 34
35 Limitations of HX Reactions HI does not react Poor yields of 1 and 2 chlorides May get alkene instead of alkyl halide Carbocation intermediate may rearrange. => AFB Q I 2007/08 35
36 Alcohols to halides Reactions with Phosphorus Halides Good yields with 1 and 2 alcohols PCl 3 for alkyl chloride (but SCl 2 better) PBr 3 for alkyl bromide P and I 2 for alkyl iodide (PI 3 not stable) => AFB Q I 2007/08 36
37 Mechanism with PBr 3 P bonds to -H as Br - leaves Br - attacks backside (S N 2) HPBr 2 leaves AFB Q I 2007/08 37
38 Reaction with Thionyl Chloride Produces alkyl chloride, S 2, HCl S bonds to -H, Cl - leaves Cl - abstracts H + from H C- bond breaks as Cl - transferred to C AFB Q I 2007/08 38
39 Dehydration Reactions Conc. H 2 S 4 produces alkene Carbocation intermediate Saytzeff product Bimolecular dehydration produces ether Low temp, 140 C and below, favors ether High temp, 180 C and above, favors alkene AFB Q I 2007/08 39
40 Dehydration Mechanisms H CH alcohol H 2 S 4 H H CH CH H 2 H 3 + H H 2 H CH 2 CH H H 2 => AFB Q I 2007/08 40
41 Energy Diagram, E1 AFB Q I 2007/08 41 =>
42 Unique Reactions of Diols Pinacol rearrangement Periodic acid cleavage AFB Q I 2007/08 42
43 Pinacol Rearrangement C H H + C C C H H H H C H C C H C C H C C H C C C pinacolone AFB Q I 2007/08 43
44 Periodic Cleavage of Glycols H C H C HI 4 C H H + C s 4 H ( ) 2 S H C C H 3 C AFB Q I 2007/08 44
45 Esterification Fischer: alcohol + carboxylic acid Tosylate esters Sulfate esters Nitrate esters Phosphate esters => AFB Q I 2007/08 45
46 Fischer Esterification Acid + Alcohol yields Ester + Water Sulfuric acid is a catalyst. Each step is reversible. C H + H CH 2 CH 2 CH H + C CH 2 CH 2 CH + HH => AFB Q I 2007/08 46
47 Tosylate Esters Alcohol +p-toluenesulfonic acid, TsH Acid chloride is actually used, TsCl CH 2 H + H S CH 2 S => + HH AFB Q I 2007/08 47
48 Sulfate Esters Alcohol + Sulfuric Acid H S H + H + H CH 2 H S CH 2 CH 2 H + H S CH 2 H + CH 2 S CH 2 => AFB Q I 2007/08 48
49 Nitrate Esters N H + H CH 2 H + N CH 2 CH 2 CH 2 H H + 3 H N 2 CH 2 CH 2 N 2 N 2 CH 2 H CH 2 N 2 glycerine nitroglycerine => AFB Q I 2007/08 49
50 Phosphate Esters H P H H P H H P H H H P H => AFB Q I 2007/08 50
51 Phosphate Esters in DNA CH 2 H H P base H CH 2 H H P base H CH 2 base H H H P CH 2 base H H H AFB Q I 2007/08 51 P =>
52 Alkoxide Ions RH + Na (or NaH) yields sodium alkoxide R alkyl halide yields ether (Williamson ether synthesis) CH 2 CH + CH 2 Br CH 2 CH 2 CH CH 2 => AFB Q I 2007/08 52
Chapter 11 Reactions of Alcohols. Types of Alcohol Reactions
hapter 11 Reactions of Alcohols Types of Alcohol Reactions Dehydration to alkene (Discussed in hap 7) xidation to aldehyde, ketone Substitution to form alkyl halide Reduction to alkane Esterification Tosylation
But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens).
Reactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations the majority of which are either oxidation or reduction type reactions. Normally: Oxidation
(Neither an oxidation or reduction: Addition or loss of H +, H 2 O, HX).
eactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations the majority of which are either oxidation or reduction type reactions. xidation is a
Oxidation of alcohols Chromic Acid KMnO4 PCC Swern 1 ROH RCOOH RCOOH RCHO RCHO 2 ROH Ketone Ketone Ketone Ketone 3 ROH NR NR NR NR
Chapter 11 xidation in rganic terms xidation Reduction Neither Addition of, X2; loss of 2 Addition of 2; loss of or X2 Anytime you oxidize one carbon but reduce another (ex. Adding and to adjacent carbons)
Alcohols. Have seen many reactions to synthesize alcohols: In this chapter we will study reactions of the alcohols
Alcohols ave seen many reactions to synthesize alcohols: In this chapter we will study reactions of the alcohols Oxidation Need to understand the nomenclature of organic reduction/oxidation In general
Learning Guide for Chapter 15 - Alcohols (II)
Learning Guide for Chapter 15 - Alcohols (II) I. Introduction to alcohol reactivity II. Reactions of alcohols with acids III. Reactions of alcohols with electrophiles alogenated phosphorus and sulfur compounds
Loudon Chapter 10 Review: Alcohols & Thiols Jacquie Richardson, CU Boulder Last updated 4/26/2016
Alcohols (R) and thiols (RS) have many reactions in common with alkyl halides, but they don t do everything exactly the same. The main difference between this and alkyl halide chemistry is that unlike
DAMIETTA 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,
Chapter 13: Alcohols and Phenols
Chapter 13: Alcohols and Phenols [ Chapter 9 Sections: 9.10; Chapter 13 Sections: 13.1-13.3, 13.9-13.10] 1. Nomenclature of Alcohols simple alcohols C3 C3C2 Eddie Sachs 1927-1964 larger alcohols find the
Alcohols, Ethers, & Epoxides
Alcohols, Ethers, & Epoxides Alcohols Structure and Bonding Enols and Phenols Compounds having a hydroxy group on a sp 2 hybridized carbon enols and phenols undergo different reactions than alcohols. Chapter
c. Oxidizing agent shown here oxidizes 2º alcohols to ketones and 1º alcohols to carboxylic acids. 3º alcohols DO NOT REACT.
Exam 1 (Ch 17 and Review of CEM 331) Answer Key: 1. ne-step Questions: You need to know reagents for reagent arrows and to be able to draw products. I know a lot of them seem to look alike its your job
Introduction & Definitions Catalytic Hydrogenations Dissolving Metal Reduction Reduction by Addition of H- and H+ Oxidation of Alcohols Oxidation of
CEM 241- UNIT 4 xidation/reduction Reactions Redox chemistry 1 utline Introduction & Definitions Catalytic ydrogenations Dissolving Metal Reduction Reduction by Addition of - and + xidation of Alcohols
Chapter 10 Outline: Alcohols
Chapter 10 Outline: Alcohols Review Nomenclature, Structure & Physical Properties on your own 1. Acidity of Alcohols 2. Reactions of Alcohols 3. Reactions of Thiols You should do all the problems in the
CHAPTER 20: MORE ABOUT OXIDATION REDUCTION REACTIONS Oxidation Reduction Reactions of Organic Compounds: An Overview
CHAPTER 20: MORE ABOUT OXIDATION REDUCTION REACTIONS In an oxidation-reduction reaction (redox reaction), one species loses electrons and one gains electrons. The species that loses electrons is oxidized,
Chapter 7: Alcohols, Phenols and Thiols
Chapter 7: Alcohols, Phenols and Thiols 45 -Alcohols have the general formula R-OH and are characterized by the presence of a hydroxyl group, -OH. -Phenols have a hydroxyl group attached directly to an
Chapter 17: Alcohols and Phenols. Based on McMurry s Organic Chemistry, 7 th edition
Chapter 17: Alcohols and Phenols Based on McMurry s Organic Chemistry, 7 th edition Alcohols and Phenols Alcohols contain an OH group connected to a a saturated C (sp 3 ) They are important solvents and
Alcohols, Ethers and Epoxides. Chapter Organic Chemistry, 8th Edition John McMurry
Alcohols, Ethers and Epoxides Chapter 17-18 Organic Chemistry, 8th Edition John McMurry 1 Introduction Structure and Bonding Alcohols contain a hydroxy group (OH) bonded to an sp 3 hybridized carbon. 2
ALCOHOLS 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
REACTIONS OF ALCOHOLS Created by: Mohammad Heidarian
Nucleophilic Substitution, β- Elimination, and Oxidation reactions are the main type of reactions associated with alcohols. Nucleophilic Substitution: A reaction in which a nucleophile replaces a leaving
Chapter 20: Carboxylic Acids
1 Chapter 20: Carboxylic Acids I. Introduction: Carboxylic acid structure: Classification of carboxylic acids: A carboxylic acid donates protons by the heterocyclic cleavage of the O-H bond, generating
Ch 17 Alcohols and Phenols
Ch 17 Alcohols and Phenols Alcohols are compounds with a hydroxyl group (OH) attached to an sp 3 C. Phenols are compounds with a hydroxyl group (OH) attached to an aromatic sp 2 C. Classification of Alcohols
Chapter 16 Alcohol, Diols, Thiols
Chapter 16 Alcohol, Diols, Thiols Alcohols are a very important functional group, which we have already seen in previous chapters. In this chapter we will review previous material and see some new ways
LECTURE #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
Chapter 20: Aldehydes and Ketones
hem A225 Notes Page 67 I. Introduction hapter 20: Aldehydes and Ketones Aldehydes and ketones contain a carbonyl group (=) with no other heteroatoms attached. An aldehyde has at least one hydrogen attached;
Module9. 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
DAMIETTA UNIVERSITY. Energy Diagram of One-Step Exothermic Reaction
DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 5 Dr Ali El-Agamey 1 Energy Diagram of One-Step Exothermic Reaction The vertical axis in this graph represents the potential energy. The transition
REACTION AND SYNTHESIS REVIEW
REACTION AND SYNTHESIS REVIEW A STUDENT SHOULD BE ABLE TO PREDICT PRODUCTS, IDENTIFY REACTANTS, GIVE REACTION CONDITIONS, PROPOSE SYNTHESES, AND PROPOSE MECHANISMS (AS LISTED BELOW). REVIEW THE MECHANISM
KOT 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
Chem 263 Nov 7, elimination reaction. There are many reagents that can be used for this reaction. Only three are given in this course:
hem 263 Nov 7, 2013 Preparation of Ketones and Aldehydes from Alcohols xidation of Alcohols [] must have at least 1 E elimination reaction [] = oxidation; removal of electrons [] = reduction; addition
CHEM 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
Chapter 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
REASONING QUESTIONS FROM ORGANIC CHEMISTRY (CH. 1 & 2)
REASONING QUESTIONS FROM ORGANIC CHEMISTRY (CH. 1 & 2) 1.) Why do haloalkenes under go nucleophillic substitution whereas haloarenes under go electophillic substitution. Ans. Due to more electro negative
Ch 19 Aldehydes and Ketones
Ch 19 Aldehydes and Ketones Aldehydes (RCHO), with the exception of formaldehyde (H 2 CO), are compounds with both an H and an organic group attached to a carbonyl. Ketones (R 2 CO) are compounds with
Electrophile = electron loving = any general electron pair acceptor = Lewis acid, (often an acidic proton)
314 Arrow Pushing practice/eauchamp 1 Electrophile = electron loving = any general electron pair acceptor = Lewis acid, (often an acidic proton) ucleophile = nucleus/positive loving = any general electron
18.8 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
acetaldehyde (ethanal)
hem 263 Nov 2, 2010 Preparation of Ketones and Aldehydes from Alkenes zonolysis 1. 3 2. Zn acetone 1. 3 2. Zn acetone acetaldehyde (ethanal) Mechanism: 3 3 3 + - oncerted reaction 3 3 3 + ozonide (explosive)
Chapter 16. Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group. Physical Properties of Aldehydes and Ketones. Synthesis of Aldehydes
Nomenclature of Aldehydes and Ketones Chapter 16 Aldehydes and Ketones I. Aldehydes replace the -e of the parent alkane with -al The functional group needs no number Nucleophilic Addition to the Carbonyl
Physical 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
Carbon-heteroatom single bonds basic C N C X. X= F, Cl, Br, I Alkyl Halide C O. epoxide Chapter 14 H. alcohols acidic H C S C. thiols.
hapter 13: Alcohols and Phenols 13.1 Structure and Properties of Alcohols Alkanes arbon - arbon Multiple Bonds arbon-heteroatom single bonds basic Alkenes X X= F, l,, I Alkyl alide amines hapter 23 nitro
Allyl radicals are especially stable due to resonance ( and double bond switch places):
Ch 10 Alkyl Halides Nomenclature Rules The parent is the longest alkyl chain or ring. The #1 C for a chain is at the end that is nearest to the first substituent. The #1 C for a ring possesses the first
Reactions of Chapter 10 Worksheet and Key
1) Alcohol Fermentation Reactions of Chapter 10 Worksheet and Key Alcohol fermentation is a series of chemical reaction that convert sugar molecules, such a glucose, into ethanol and C 2. The overall reaction
Basic Organic Chemistry
Basic rganic hemistry ourse code: EM 12162 (Pre-requisites : EM 11122) hapter 06 hemistry of Aldehydes & Ketones Dr. Dinesh R. Pandithavidana ffice: B1 222/3 Phone: (+94)777-745-720 (Mobile) Email: dinesh@kln.ac.lk
Mechanisms. . 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
Chapter 17 Alcohols and Phenols
Chapter 17 Alcohols and Phenols Alcohols and Phenols Organic derivatives of water One of water s hydrogens is replaced by an organic group Alcohols contain an OH group connected to a saturated, sp 3 -hybridized
CHEMISTRY Topic #8: Oxidation and Reduction Reactions Fall 2018 Dr. Susan Findlay
CEMISTRY 2600 Topic #8: xidation and Reduction Reactions Fall 2018 Dr. Susan Findlay xidation States of Carbon Carbon can have any oxidation state from -4 (C 4 ) to +4 (C 2 ). As a general rule, increasing
Chapter 19 Substitutions at the Carbonyl Group
Chapter 19 Substitutions at the Carbonyl Group In Chapter 18 Additions to the Carbonyl Groups In Chapter 19 Substitutions at the Carbonyl Group O O - - O - O R Y R C+ Y R Y Nu -Ȳ R N u + Y=goodleavinggroup
Background Information
ackground nformation ntroduction to Condensation eactions Condensation reactions occur between the α-carbon of one carbonyl-containing functional group and the carbonyl carbon of a second carbonyl-containing
Synthesis 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
Organic Chemistry Lecture 2 - Hydrocarbons, Alcohols, Substitutions
ALKANES Water-insoluble, low density C-C single bonds Higher MW -> higher BP, higher MP Branching -> lower BP, higher MP Forms cycloalkanes which can have ring strain Cyclohexane: chair vs. boat configuration
Chapter 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
Organic 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,
OCR (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
Chapter 1 Reactions of Organic Compounds. Reactions Involving Hydrocarbons
Chapter 1 Reactions of Organic Compounds Reactions Involving Hydrocarbons Reactions of Alkanes Single bonds (C-C) are strong and very hard to break, therefore these compounds are relatively unreactive
CARBONYL 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
Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides
Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides Learning objectives: 1. Provide both IUPAC and common (when applicable) names for alcohols and ethers. 2. Describe the physical properties
Carbonyl Chemistry. aldehydes ketones. carboxylic acid and derivatives. Wednesday, April 29, 2009
Carbonyl Chemistry X aldehydes ketones carboxylic acid and derivatives Electrophiles (eg. + ) Nucleophiles (eg. C 3 MgBr) an enolate Base β β β α α α 1 2 3 4 Nuc- 1 2 Nuc 3 4 1,2-addition 1 2 3 4 Nuc-
Essential Organic Chemistry. Chapter 9
Essential Organic Chemistry Paula Yurkanis Bruice Chapter 9 Substitution and Elimination Reactions of Alkyl Halides 9.1 How Alkyl Halides React Substitution Reactions One group takes the place of another.
Chapter 17: Alcohols and Phenols
hapter 17: Alcohols and Phenols sp 3 alcohol phenol (aromatic alcohol) pka~ 16-18 pka~ 10 Alcohols contain an group connected to a saturated carbon (sp 3 ) Phenols contain an group connected to a carbon
Aldehydes and Ketones Reactions. Dr. Sapna Gupta
Aldehydes and Ketones Reactions Dr. Sapna Gupta Reactions of Aldehydes and Ketones Nucleophilic Addition A strong nucleophile attacks the carbonyl carbon, forming an alkoxide ion that is then protonated.
Chapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group
Chapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al
Chapter 7: Alcohols, Phenols and Thiols
Chapter 7: Alcohols, Phenols and Thiols Nomenclature of Alcohols In the IUPAC system, the hydroxyl group in alcohols is indicated by the ending ol. In common names, the separate word alcohol is placed
CHM252/Spring 12 Assignment: Chapter 17 & 18
CHM252/Spring 12 Assignment: Chapter 17 & 18 We will spend the first 2 weeks reviewing and covering the chemistry of alcohols, phenols, ethers, epoxides & their sulfur analogs the thiols and sulfides.
CHEMISTRY 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:
TOK: 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
Name/CG: 2012 Term 2 Organic Chemistry Revision (Session II) Deductive Question
Name/G: 2012 Term 2 rganic hemistry Revision (Session II) Deductive Question 1(a) A yellow liquid A, 7 7 N 2, reacts with alkaline potassium manganate (VII) and on acidification gives a yellow solid B,
Carboxylic 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
Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group
Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al
Available chemicals from the catalog (the starting sources of carbon compounds will continually decrease as we learn new reactions.
ucleophilic ubstitution & Elimination Chemistry Beauchamp 1 Available chemicals from the catalog (the starting sources of carbon compounds will continually decrease as we learn new reactions. ources of
Alcohols: Contain a hydroxy group( OH) bonded to an sp 2 or sp 3 hybridized
Lecture Notes hem 51B S. King hapter 9 Alcohols, Ethers, and Epoxides I. Introduction Alcohols, ether, and epoxides are 3 functional groups that contain σ-bonds. Alcohols: ontain a hydroxy group( ) bonded
CHEMISTRY MIDTERM # 2 November 02, The total number of points in this midterm is 100. The total exam time is 120 min (2 h). Good luck!
CEMISTRY 314-01 MIDTERM # 2 November 02, 2009 Name... The total number of points in this midterm is 100. The total exam time is 120 min (2 h). Good luck! 1. (8 pts) Mark as true (T) or false (F) the following
Chapter 12. Alcohols from Carbonyl Compounds Oxidation-Reduction & Organometallic Compounds. Structure
Chapter 12 Alcohols from Carbonyl Compounds xidation-eduction & rganometallic Compounds Created by Professor William Tam & Dr. Phillis Chang Structure ~ 120 o ~ 120 o C ~ 120 o Carbonyl carbon: sp 2 hybridized
Chapter 20: Aldehydes and Ketones
Chapter 20: Aldehydes and Ketones [Chapter 20 Sections: 20.1-20.7, 20.9-10.10, 20.13] 1. Nomenclature of Aldehydes and Ketones ' ketone aldehyde f both aldehydes and ketones, the parent chain is the longest
Chem 263 Notes March 2, 2006
Chem 263 Notes March 2, 2006 Average for the midterm is 102.5 / 150 (approx. 68%). Preparation of Aldehydes and Ketones There are several methods to prepare aldehydes and ketones. We will only deal with
Chapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds
Chapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds Introduction Several functional groups contain the carbonyl group Carbonyl groups can be converted into alcohols
CARBOXYLIC ACIDS and their Derivatives Nucleophilic Acyl substitution - Review the nomenclature for these compounds in your textbook
CARBXYLIC ACIDS and their Derivatives Nucleophilic Acyl substitution - Review the nomenclature for these compounds in your textbook R Z R Z R Z - the basicity of Z determines the relative stability of
CHEM 203. Final Exam December 12, This a closed-notes, closed-book exam. You may use your set of molecular models. This test contains 11 pages
CEM 203 Final Exam December 12, 2012 Your name: This a closed-notes, closed-book exam You may use your set of molecular models This test contains 11 pages Time: 2h 30 min 1. / 20 2. / 24 3. / 26 4. / 30
Chem HH W13-Notes Dr. Masato Koreeda - Page 1 of 13 Date: February 20, 2013
hem 215-216 W13-otes Dr. Masato Koreeda - Page 1 of 13 Date: February 20, 2013 hapter 13. Alcohols, Diols, and Ethers verview: hemistry and reactions of sp 3 oxygen groups, particularly oxidation of an
Alcohols. Contents. Structure. structure
Page 1 of 9 Alcohols Contents structure Physical Properties Classification of Alcohols Nomenclature of Alcohols Preparation of Alcohols Oxidation of Alcohols oxidation of aldehydes Structure Alcohols can
Chemistry 2030 Introduction to Organic Chemistry Fall Semester 2017 Dr. Rainer Glaser
Chemistry 2030 Introduction to Organic Chemistry Fall Semester 2017 Dr. Rainer Glaser Examination #3 Nucleophilic Substitutions & Eliminations, Alcohols, and Ethers Thursday, November 2, 2017, 8:25-9:15
Chapter 18 Ketones and Aldehydes. Carbonyl Compounds. Chapter 18: Aldehydes and Ketones Slide 18-2
hapter 18 Ketones and Aldehydes arbonyl ompounds hapter 18: Aldehydes and Ketones Slide 18-2 1 arbonyl Structure arbon is sp 2 hybridized. = bond is shorter, stronger, and more polar than = bond in alkenes.
ORGANIC - 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
Alpha Substitution and Condensations of Enols and Enolate Ions. Alpha Substitution
Alpha Substitution and ondensations of Enols and Enolate Ions hap 23 W: 27, 28, 30, 31, 37, 39, 42-44, 47, 51, 54-56 Alpha Substitution Replacement of a hydrogen on the carbon adjacent to the carbonyl,
Classification Tests
3CLASFIC.DC 10/23/2008 Classification Tests 1. Classification Tests For Alcohols a) Sodium Metal: RH Na RNa H2(g) Positive Test: evolution of gas the rate is highly variable and depends upon the alcohol
2.222 Practice Problems 2003
2.222 Practice Problems 2003 Set #1 1. Provide the missing starting compound(s), reagent/solvent, or product to correctly complete each of the following. Most people in the class have not done this type
CHM 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
Chapter 20 Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution
ucleophilic Acyl Substitution hapter 20 arboxylic Acid Derivatives ucleophilic Acyl Substitution Y (1) need to have Y as a u Y u u + Y (2) could not happen with aldehydes or ketones as : and : are poor
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
S N 2 and E2 Mechanisms (strong base/nucleophile competition reacting at a carbon or reacting at a proton)
Electrophile (Lewis Acid) = electron loving = any general electron pair acceptor (can also be an acidic proton = onsted acid) ucleophile (Lewis Base) = nucleus/positive loving = any general electron pair
Downloaded from
1 Class XII Chemistry Chapter: Alcohols, Phenols And Ethers Top concepts: 1. Structure of alcohols, phenols and ethers: 2. Preparation of alcohols: 3. Preparation of phenols: 2 4. Physical properties of
Chem 350 Jasperse Ch. 11 Handouts 1. Summary of Alcohol Reactions, Ch. 11.
Chem 350 Jasperse Ch. 11 andouts 1 Summary of Alcohol eactions, Ch. 11.??? 1 + NaZ Na Acid-Base + Z 1. Deprotonation by a base. 2. Controlled by relative stability of versus Z. 3. Consider relative electronegativity
Chapter 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
UNIT 11 ALCOHOLS, PHENOLS & ETHERS
UNIT 11 ALCOHOLS, PHENOLS & ETHERS Alcohols and Phenol are Organic compound with a hydroxyl group (- OH) as functional group. Ethers are identified by a functional group ( 0 ). Cyclic alcohols are named
ALCOHOLS AND PHENOLS; ETHERS AND EPOXIDES; THIOLS AND SULFIDES
ALCOHOLS AND PHENOLS; ETHERS AND EPOXIDES; THIOLS AND SULFIDES A STUDENT SHOULD BE ABLE TO: 1. Give the IUPAC name when given the structure, and draw the structure given the name of open-chain and monocyclic
ELECTROPHILIC ADDITIONS OF ALKENES AS THE COUNTERPART OF ELIMINATIONS
ELECTRPHILIC ADDITINS F ALKENES AS THE CUNTERPART F ELIMINATINS INTRDUCTIN - Chapter 8 is mostly about alkene reactions. That is, how one can transform alkenes into other functional groups. Most of these
Chemistry 335 Supplemental Slides: Interlude 1. Reduction: addition of hydrogen to the substrate. Oxidation: addition of oxygen to the substrate
Interlude 1: Oxidations, Reductions & Other Functional Group Interconversions (FGI) 1. Definition of Oxidation and Reduction For practical purposes in organic chemistry, oxidation and reduction are defined
Chapter 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
Chemistry 52 Exam #2. Name: 5 February This exam has six (6) questions, two cover pages, six exam pages, and three scratch pages.
Chemistry 52 Exam #2 Name: 5 February 2003 This exam has six (6) questions, two cover pages, six exam pages, and three scratch pages. Please check before beginning to make sure no questions are missing.
Chapter 17 Reactions of Aromatic Compounds. Electrophilic Aromatic Substitution
Chapter 17 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Electrophile substitutes for a hydrogen on the benzene ring. Chapter 17: Aromatics 2-Reactions Slide 17-2 1 Mechanism Step
Chapter 11 - Alcohols and Ethers 1
Andrew Rosen Chapter 11 - Alcohols and Ethers 1 11.1 - Structure and Nomenclature - The common naming calls alcohols as alkyl alcohols (eg: methyl alcohol) - The common names of ethers have the groups
CHEM 203. Final Exam December 18, This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Final Exam December 18, 2013 Your name: This a closed-notes, closed-book exam You may use your set of molecular models This test consists of 10 pages Time: 2h 30 min 1. / 20 2. / 20 3. / 30 4.