Alcohols and Phenols
|
|
- Georgiana Kennedy
- 6 years ago
- Views:
Transcription
1 Chapter 17- Alcohols and Phenols Alcohols and Phenols Alcohols contain an OH group connected to a a saturated C (sp 3 ) They are important solvents and synthesis intermediates Phenols contain an OH group connected to a carbon in a benzene ring 1
2 Alcohols and Phenols Methanol, CH 3 OH, called methyl alcohol, is a common solvent, a fuel addigve, produced in large quangges Ethanol, CH 3 CH 2 OH, called ethyl alcohol, is a solvent, fuel, beverage Phenol, C 6 H 5 OH ( phenyl alcohol ) has diverse uses - it gives its name to the general class of compounds OH groups bonded to vinylic, sp 2 -hybridized carbons are called enols Why do I care, Dr. P? To begin to study oxygen-containing funcgonal groups These groups lie at the heart of biological chemistry 2
3 Nomenclature General classificagons of alcohols based on subsgtugon on C to which OH is apached Methyl (C has 3 H s), Primary (1 ) (C has two H s, one R), Secondary (2 ) (C has one H, two R s), TerGary (3 ) (C has no H, 3 R s), IUPAC Rules for Naming Alcohols 1) Select the longest carbon chain containing the hydroxyl group, and derive the parent name by replacing the -e ending of the corresponding alkane with -ol 2) Number the chain from the end nearer the hydroxyl group 3) Number subsgtuents according to posigon on chain, lisgng the subsgtuents in alphabegcal order 3
4 Naming Phenols Use phenol (the French name for benzene) as the parent hydrocarbon name, not benzene Name subsgtuents on aromagc ring by their posigon from OH Learning check Give the correct IUPAC names for the following compounds. OH Cl O 2 N HO H 4
5 Properties of Alcohols and Phenols The structure around O of the alcohol or phenol is similar to that in water, sp 3 hybridized Alcohols and phenols have much higher boiling points than similar alkanes and alkyl halides Why do you think alcohols and phenols have high boiling points? Properties of Alcohols and Phenols: Acidity and Basicity Weakly basic and weakly acidic Alcohols are weak Brønsted bases Protonated by strong acids to yield oxonium ions, ROH 2 + 5
6 Alcohols and Phenols are Weak Brønsted Acids Can transfer a proton to water to a very small extent Produces H 3 O + and an alkoxide ion, RO -, or a phenoxide ion, ArO - Acidity Measurements The acidity constant, K a, measures the extent to which a Brønsted acid transfers a proton to water [A - ] [H 3 O + ] K a = and pk a = -log K a [HA] RelaGve acidiges are more conveniently presented on a logarithmic scale, pk a, which is directly proporgonal to the free energy of the equilibrium What is the relagonship between pk a and the strength of the acid? Differences in pk a correspond to differences in free energy 6
7 pk a Values for Typical OH Compounds Relative Acidities of Alcohols Simple alcohols are about as acidic as water Alkyl groups make an alcohol a weaker acid The more easily the alkoxide ion is solvated by water the more its formagon is energegcally favored 7
8 Inductive Effects Electron-withdrawing groups make an alcohol a stronger acid by stabilizing the conjugate base (alkoxide) Generating Alkoxides from Alcohols Alcohols are weak acids requires a strong base to form an alkoxide such as NaH, sodium amide NaNH 2, and Grignard reagents (RMgX) Alkoxides are bases used as reagents in organic chemistry 8
9 Phenol Acidity Phenols (pk a ~10) are much more acidic than alcohols (pk a ~ 16) due to resonance stabilizagon of the phenoxide ion Phenols react with NaOH solugons (but alcohols do not), forming salts that are soluble in dilute aqueous solugon Why is this important in the laboratory? Nitro-Phenols Phenols with nitro groups at the ortho and para posigons are much stronger acids 9
10 Learning check The following data for isomeric four-carbon alcohols show that there is a decrease in boiling point with increasing subsgtugon of the OH-bearing carbon. How might you account for this trend? 1-butanol, bp C 2-butanol, bp 99.5 C 2-methyl-2-propanol, bp 82.2 C Preparation of Alcohols: A Review Alcohols are derived from many types of compounds The alcohol can be converted to many other funcgonal groups 10
11 Preparation of Alcohols What are some ways you can prepare alcohols from alkenes? Review: Preparation of Alcohols by Regiospecific Hydration of Alkenes HydroboraGon/oxidaGon: syn, non-markovnikov hydragon OxymercuraGon/reducGon: Markovnikov hydragon 11
12 1,2-Diols Cis-1,2-diols from hydroxylagon of an alkene with OsO 4 followed by reducgon with NaHSO 3 Trans-1,2-diols from acid-catalyzed hydrolysis of epoxides Learning check Predict the products of the following reacgons: 1. OsO 4, pyridine 2. NaHSO 3, H 2 O 1. Hg(OAc) 2, H 2 O 2. NaBH 4 12
13 Alcohols from Reduction of Carbonyl Compounds ReducGon of a carbonyl compound in general gives an alcohol Note that organic reducgon reacgons add the equivalent of H 2 to a molecule Reduction of Aldehydes and Ketones Aldehydes produce primary alcohols Ketones produce secondary alcohols 13
14 Reducing Reagent: Sodium Borohydride NaBH 4 is not sensigve to moisture and it does not reduce other common funcgonal groups Lithium aluminum hydride (LiAlH 4 ) is more powerful, less specific, and very reacgve with water Both add the equivalent of H - Mechanism of Reduction The reagent adds the equivalent of hydride to the carbon of C=O and polarizes the group as well 14
15 Reduction of Carboxylic Acids and Esters Carboxylic acids and esters are reduced to give primary alcohols LiAlH 4 is used because NaBH 4 is not effecgve Alcohols from Reaction of Carbonyl Compounds with Grignard Reagents Alkyl, aryl, and vinylic halides react with magnesium in ether or tetrahydrofuran to generate Grignard reagents, RMgX Grignard reagents react with carbonyl compounds to yield alcohols 15
16 Reactions of Grignard Reagents with Carbonyl Compounds Reactions of Esters and Grignard Reagents Yields tergary alcohols in which two of the subsgtuents come from the Grignard reagent Grignard reagents do not add to carboxylic acids they undergo an acid-base reacgon, generagng the hydrocarbon of the Grignard reagent 16
17 Grignard Reagents and Other Functional Groups in the Same Molecule Can't be prepared if there are reacgve funcgonal groups in the same molecule, including proton donors Mechanism of the Addition of a Grignard Reagent Grignard reagents act as nucleophilic carbon anions (carbanions, : R-) in adding to a carbonyl group The intermediate alkoxide is then protonated to produce the alcohol 17
18 Learning check Predict the product of the following reacgons below. MgBr + O 1. ether 2. H 3 O + O OH 1. LiAlH 4, ether 2. H 3 O + Reactions of Alcohols Conversion of alcohols into alkyl halides: - 3 alcohols react with HCl or HBr by S N 1 through carbocagon intermediate - 1 and 2 alcohols converted into halides by treatment with SOCl 2 or PBr 3 via S N 2 mechanism 18
19 Conversion of Alcohols into Tosylates ReacGon with p-toluenesulfonyl chloride (tosyl chloride, p-toscl) in pyridine yields alkyl tosylates, ROTos FormaGon of the tosylate does not involve the C O bond so configuragon at a chirality center is maintained Alkyl tosylates react like alkyl halides 19
20 Stereochemical Uses of Tosylates The S N 2 reacgon of an alcohol via a tosylate, produces inversion at the chirality center The S N 2 reacgon of an alcohol via an alkyl halide proceeds with two inversions, giving product with same arrangement as stargng alcohol Dehydration of Alcohols to Yield Alkenes The general reacgon: forming an alkene from an alcohol through loss of O-H and H (hence dehydragon) of the neighboring C H to give π bond 20
21 Acid- Catalyzed Dehydration TerGary alcohols are readily dehydrated with acidwhy is 2-methyl-2-butene the major product? Secondary alcohols require severe condigons (75% H 2 SO 4, 100 C) - sensigve molecules don't survive Primary alcohols require very harsh condigons impracgcal ReacGvity is the result of the nature of the carbocagon intermediate 21
22 Dehydration with POCl 3 Phosphorus oxychloride in the amine solvent pyridine can lead to dehydragon of secondary and tergary alcohols at low temperatures An E2 via an intermediate ester of POCl 2 22
23 Conversion of Alcohols into Esters Learning check Predict the product for the following reacgon below. H OH 1. p-toscl, pyridine 2. NaOCH 3, CH 3 OH 23
24 Oxidation of Alcohols Can be accomplished by inorganic reagents, such as KMnO 4, CrO 3, and Na 2 Cr 2 O 7 or by more selecgve, expensive reagents Oxidation of Primary Alcohols To aldehyde: pyridinium chlorochromate (PCC, C 5 H 6 NCrO 3 Cl) in dichloromethane Other reagents produce carboxylic acids 24
25 Oxidation of Secondary Alcohols EffecGve with inexpensive reagents such as Na 2 Cr 2 O 7 in acegc acid PCC is used for sensigve alcohols at lower temperatures Mechanism of Chromic Acid Oxidation Alcohol forms a chromate ester followed by eliminagon with electron transfer to give ketone The mechanism was determined by observing the effects of isotopes on rates 25
26 Protection of Alcohols Hydroxyl groups can easily transfer their proton to a basic reagent This can prevent desired reacgons ConverGng the hydroxyl to a (removable) funcgonal group without an acidic proton protects the alcohol Methods to Protect Alcohols ReacGon with chlorotrimethylsilane in the presence of base yields an unreacgve trimethylsilyl (TMS) ether The ether can be cleaved with acid or with fluoride ion to regenerate the alcohol 26
27 Protection-Deprotection An example of TMS-alcohol protecgon in a synthesis Reactions of Phenols The hydroxyl group is a strongly acgvagng, making phenols substrates for electrophilic halogenagon, nitragon, sulfonagon, and Friedel Crats reacgons ReacGon of a phenol with strong oxidizing agents yields a quinone Fremy's salt [(KSO 3 ) 2 NO] works under mild condigons through a radical mechanism 27
28 Quinones in Nature Ubiquinones mediate electron-transfer processes involved in energy producgon through their redox reacgons Spectroscopy of Alcohols and Phenols CharacterisGc O H stretching absorpgon at 3300 to 3600 cm -1 in the infrared Sharp absorpgon near 3600 cm -1 except if H-bonded: then broad absorpgon 3300 to 3400 cm -1 range Strong C O stretching absorpgon near 1050 cm -1 Phenol OH absorbs near 3500 cm -1 28
29 IR spectrum 29
30 Nuclear Magnetic Resonance Spectroscopy 13 C NMR: C bonded to OH absorbs at a lower field, δ 50 to 80 1 H NMR: electron-withdrawing effect of the nearby oxygen, absorbs at δ 3.5 to 4 (See Figure 17-13) Usually no spin-spin coupling between O H proton and neighboring protons on C due to exchange reacgons with moisture or acids Spin spin spliung is observed between protons on the oxygen-bearing carbon and other neighbors Phenol O H protons absorb at δ 3 to 8 NMR spectrum 30
31 Mass Spectrometry Alcohols undergo alpha cleavage, a C C bond nearest the hydroxyl group is broken, yielding a neutral radical plus a charged oxygen-containing fragment Alcohols undergo dehydragon to yield an alkene radical anion Mass Spectrum 31
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
More informationChapter 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
More informationAlcohols and Phenols and Their Reac1ons
Alcohols and Phenols and Their Reac1ons More About the Families in Group II The families in Group II all have an electronega1ve atom or group that is a>ached to an sp 3 carbon. Alcohols and Phenols Alcohols
More informationCh 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
More informationChapter 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
More informationChapter 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
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 informationChapter 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
More informationAlcohols, 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
More informationBut 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
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 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
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 informationSynthesis and Structure of Alcohols Alcohols can be considered organic analogues of water.
Synthesis and Structure of Alcohols Alcohols can be considered organic analogues of water. Alcohols are usually classified as primary, secondary and tertiary. Alcohols with the hydroxyl bound directly
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 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 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 informationAlcohols. Alcohol any organic compound containing a hydroxyl (R-OH) group. Alcohols are an extremely important organic source
Alcohols Alcohol any organic compound containing a hydroxyl (R-OH) group Uses: synthetic intermediate, cleanser, cosmetics, fuel, alcoholic beverages, etc. Alcohols are an extremely important organic source
More informationAlcohols Classification
Alcohols Alcohols are compounds of the general formula ROH, where R is any alkyl or substituted alkyl group. The group may be primary, secondary, or tertiary; it may be open-chain or cyclic; it may contain
More informationALCOHOLS 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
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 informationDAMIETTA 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
More informationCarbon-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
More informationCh 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
More information75. A This is a Markovnikov addition reaction. In these reactions, the pielectrons in the alkene act as a nucleophile. The strongest electrophile will
71. B SN2 stands for substitution nucleophilic bimolecular. This means that there is a bimolecular rate-determining step. Therefore, the reaction will follow second-order kinetics based on the collision
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 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 informationChapter 19 Carboxylic Acids
Carboxylic acids have the formula RCO2H. Nomenclature Chapter 19 Carboxylic Acids For the parent alkane, drop the terminal e and add the suffix oic acid. The parent alkane is the longest continuous chain
More informationAlcohol Synthesis. Dr. Sapna Gupta
Alcohol Synthesis Dr. Sapna Gupta Synthesis of Alcohols Alcohols can be synthesized from several functional groups. Nucleophilic substitution of O - on alkyl halide ydration of alkenes water in acid solution
More informationDownloaded 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
More informationORGANIC - BROWN 8E CH ALDEHYDES AND KETONES.
!! 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 informationEthers. Synthesis of Ethers. Chemical Properties of Ethers
Page 1 of 6 like alcohols are organic derivatives of water, but lack the labile -OH group. As a result, ethers, except for epoxides, are usually not very reactive and are often used as solvents for organic
More informationDr. Mohamed El-Newehy
By Dr. Mohamed El-Newehy Chemistry Department, College of Science, King Saud University http://fac.ksu.edu.sa/melnewehy Aldehydes and Ketones 1 Structure of Aldehydes and Ketones - Aldehydes and ketones
More informationAlcohols, 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
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 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 informationChapter 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
More informationChapter 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
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 informationChem 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
More informationChapter 18: Ketones and Aldehydes. I. Introduction
1 Chapter 18: Ketones and Aldehydes I. Introduction We have already encountered numerous examples of this functional group (ketones, aldehydes, carboxylic acids, acid chlorides, etc). The three-dimensional
More informationChapter 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
More informationChapter 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
More informationCh 18 Ethers and Epoxides
Ch 18 Ethers and Epoxides Ethers (R-O-R ) are compounds with two organic groups attached to an sp 3 oxygen. Epoxides are cyclic ethers where the sp 3 O is a part of a 3-membered ring. Thiols (R-S-H ) and
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 informationQuímica Orgânica I. Ciências Farmacêuticas Bioquímica Química AFB QO I 2007/08 1
Química Orgânica I Ciências Farmacêuticas Bioquímica Química AFB QO I 2007/08 1 alcohols Adaptado de Organic Chemistry, 6th Edition; Wade Organic Chemistry, 6 th Edition; McMurry Organic Chemistry, 5 th
More informationAldehydes and Ketones: Nucleophilic Addition Reactions
Aldehydes and Ketones: Nucleophilic Addition Reactions Why this Chapter? Much of organic chemistry involves the chemistry of carbonyl compounds Aldehydes/ketones are intermediates in synthesis of pharmaceutical
More informationChem 251 Fall Learning Objectives
Learning Objectives Chapter 8 (last semester) 1. Write an electron-pushing mechanism for an SN2 reaction between an alkyl halide and a nucleophile. 2. Describe the rate law and relative rate of reaction
More informationChapter 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
More informationCh.17 Alcohols and Phenols
Ch.17 Alcohols and Phenols C An alcohol A phenol An enol - Me: wood alcohol: made from wood - industrial preparation of methanol: C + 2 2 400 o C Zinc oxide/chromia C 3 - Ethanol: fermentation of grains
More informationALCOHOLS: Properties & Preparation
ALLS: Properties & Preparation General formula: -, where is alkyl or substitued alkyl. Ar-: phenol - different properties. Nomenclature 1. ommon names: Name of alkyl group, followed by word alcohol. 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 informationAlkyl Halides React with Nucleophiles and Bases
Chapter 11- Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations Ashley Piekarski, Ph.D. Alkyl Halides React with Nucleophiles and Bases Alkyl halides are polarized at the carbon- halide
More informationc. 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
More informationChapter 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
More informationAlcohols. 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
More informationChapter 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
More informationCOURSE OBJECTIVES / OUTCOMES / COMPETENCIES.
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES. By the end of the course, students should be able to do the following: See Test1-4 Objectives/Competencies as listed in the syllabus and on the main course
More informationCarboxylic Acids O R C + H + O - Chemistry 618B
arboxylic Acids R H R + H + - R - Nomenclature - IUPA IUPA names: drop the -e from the parent alkane and add the suffix -oic acid If the compound contains a carbon-carbon double bond, change the infix
More informationLecture 3: Aldehydes and ketones
Lecture 3: Aldehydes and ketones I want to start by talking about the mechanism of hydroboration/ oxidation, which is a way to get alcohols from alkenes. This gives the anti-markovnikov product, primarily
More informationChem 261 Dec 6, 2017
209 Chem 261 Dec 6, 2017 REVIEW: Example: K!! + 3 C + 3 C K tert-butoxide (an alkoxide) methanol tert-butanol pka = 16 pka = 19 methoxide stronger base stronger acid (lower pka, more acidic) weaker acid
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 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 informationChapter 8: Ethers and Epoxides. Diethyl ether in starting fluid
Chapter 8: Ethers and Epoxides Diethyl ether in starting fluid 8.1 Nomenclature of Ethers Ethers are usually named by giving the name of each alkyl or aryl group, in alphabetical order, followed by the
More information21.1 Introduction Carboxylic Acids Nomenclature of Carboxylic Acids. Acids Structure and Properties of Carboxylic Acids.
21.1 Introduction Carboxylic Acids Carboxylic acids are abundant in nature and in pharmaceuticals. 21.1 Introduction Carboxylic Acids The US produces over 2.5 million tons of acetic acid per year, which
More informationJEFFERSON COLLEGE COURSE SYLLABUS CHM201 ORGANIC CHEMISTRY II. 5 Credit Hours. Prepared by: Richard A. Pierce
JEFFERSON COLLEGE COURSE SYLLABUS CHM201 ORGANIC CHEMISTRY II 5 Credit Hours Prepared by: Richard A. Pierce Revised Date: January 2008 by Ryan H. Groeneman Arts & Science Education Dr. Mindy Selsor, Dean
More informationLearning Guide for Chapter 14 - Alcohols (I)
Learning Guide for Chapter 14 - Alcohols (I) I. Introduction to Alcohols and Thiols II. Acid/base Behavior of Alcohols, Phenols, and Thiols III. Nomenclature of Alcohols IV. Synthesis of Alcohols Previous
More informationOrganic 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
More informationChapter 9 Aldehydes and Ketones
Chapter 9 Aldehydes and Ketones 9.1 Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al The aldehyde functional group is always carbon
More information8-3 This exercise is worked out on page 293 as "Working with Concepts".
Copyright 2009 James K Whitesell 8-1 This exercise combines your knowledge of basic nomenclature rules and concepts of stereochemistry introduced in Chapters 4 and 5. 8-2 Keep in mind that faculty at UCSD
More information10. Alkyl Halides. What Is an Alkyl Halide. An organic compound containing at least one carbonhalogen
10. Alkyl Halides What Is an Alkyl Halide An organic compound containing at least one carbonhalogen bond (C-X) X (F, Cl, Br, I) replaces H Can contain many C-X bonds Properties and some uses Fire-resistant
More informationAldehydes and Ketones. Dr. Munther A. M. Ali
Aldehydes and Ketones Dr. Munther A. M. Ali ALDYHYDES AND KETONES Aldehydes are compounds of the general formula RCHO Ketones are compounds of the general formula RR'CO Aldehydes A ketone Both aldehydes
More informationCh 22 Carbonyl Alpha ( ) Substitution
Ch 22 Carbonyl Alpha () Substitution The overall reaction replaces an H with an E + The acid-catalyzed reaction has an enol intermediate The base-catalyzed reaction has an enolate intermediate Keto-Enol
More informationOrganic Chemistry I: Reactions and Overview
Organic Chemistry I: Reactions and Overview Andrew Rosen Editor: Raghav Malik January 13, 2013 Contents I Library of Synthetic Reactions 3 II Organic Trends and Essentials 4 1 The Basics: Bonding and Molecular
More informationAlkyl phenyl ketones are usually named by adding the acyl group as prefix to phenone.
Aldehydes, Ketones and Carboxylic Acids Nomenclature of aldehydes and ketones Aldehydes: Often called by their common names instead of IUPAC names. Ketones: Derived by naming two alkyl or aryl groups bonded
More informationChemistry 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
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 informationREASONING 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
More informationClass XII Chapter 11 Alcohols Phenols and Ethers Chemistry. Question 11.1: Write IUPAC names of the following compounds: (i) (ii) (iii) (iv) (v) (vi)
Question 11.1: Write IUPAC names of the following compounds: (iii) (iv) (v) (vi) (vii) (viii) Page 1 of 37 (ix) (x) (xi) (xii) 2, 2, 4-Trimethylpentan-3-ol 5-Ethylheptane-2, 4-diol (iii) Butane-2, 3-diol
More information(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
More informationCHM 292 Final Exam Answer Key
CHM 292 Final Exam Answer Key 1. Predict the product(s) of the following reactions (5 points each; 35 points total). May 7, 2013 Acid catalyzed elimination to form the most highly substituted alkene possible
More 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 informationREACTION 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
More informationChapter 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
More informationChap 11. Carbonyl Alpha-Substitution Reactions and Condensation Reactions
Chap 11. Carbonyl Alpha-Substitution eactions and Condensation eactions Four fundamental reactions of carbonyl compounds 1) Nucleophilic addition (aldehydes and ketones) ) Nucleophilic acyl substitution
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 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 informationChem 263 March 7, 2006
Chem 263 March 7, 2006 Aldehydes and Ketones Aldehydes and ketones contain a carbonyl group, in which the carbon atom is doubly bonded to an oxygen atom. The carbonyl group is highly polarized, with a
More informationOrganic Chemistry 1 CHM 2210 Exam 4 (December 10, 2001)
Exam 4 (December 10, 2001) Name (print): Signature: Student ID Number: There are 12 multiple choice problems (4 points each) on this exam. Record the answers to the multiple choice questions on THIS PAGE.
More informationChapter 17. Alcohols and Phenols. Alcohols and Phenols. Naming Alcohols and Phenols
hapter 17 Alcohols and Phenols Alcohols and Phenols - alcohols - compounds that have hydroxyl groups bonded to saturated, sp 3 -hybridized carbon atoms - phenols - compounds that have hydroxyl groups bonded
More informationDetailed Course Content
Detailed Course Content Chapter 1: Carbon Compounds and Chemical Bonds The Structural Theory of Organic Chemistry 4 Chemical Bonds: The Octet Rule 6 Lewis Structures 8 Formal Charge 11 Resonance 14 Quantum
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 informationChapter 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
More information24.4: Acidity of Phenols. Phenols are more acidic than aliphatic alcohols. + Electron-withdrawing groups make an O
Chapter 24: Phenols. Alcohols contain an group bonded to an sp 3 -hybridized carbon. Phenols contain an group bonded to an sp 2 -hybridized carbon of a benzene ring 24.1: Nomenclature (please read) 24.2:
More informationLecture Notes Chem 51C S. King. Chapter 20 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation & Reduction
Lecture Notes Chem 51C S. King Chapter 20 Introduction to Carbonyl Chemistry; rganometallic Reagents; xidation & Reduction I. The Reactivity of Carbonyl Compounds The carbonyl group is an extremely important
More informationORGANIC - CLUTCH CH ALCOHOLS AND CARBONYL COMPOUNDS.
!! www.clutchprep.com CONCEPT: INTRO TO REDOX Oxidation reactions involve an increase in the content of a molecule Reduction reactions involve an increase in the content of a molecule EXAMPLE: Label the
More informationChapter 25: The Chemistry of Life: Organic and Biological Chemistry
Chemistry: The Central Science Chapter 25: The Chemistry of Life: Organic and Biological Chemistry The study of carbon compounds constitutes a separate branch of chemistry known as organic chemistry The
More informationChapter 20. Amines. Nomenclature for amines. Aryl amines
Nomenclature for amines Chapter 20 Common names are widely used, named as alkylamines Systematic (IUPAC) nomenclature replaces the -e of the corresponding parent alkane with -amine Amines Simple secondary
More 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 informationChapter 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
More information