Chapter 20: Aldehydes and Ketones
|
|
- Roland Powell
- 5 years ago
- Views:
Transcription
1 Chapter 20: Aldehydes and Ketones [Chapter 20 Sections: , , 20.13] 1. Nomenclature of Aldehydes and Ketones ' ketone aldehyde f both aldehydes and ketones, the parent chain is the longest continuous carbon chain that contains the carbon of the carbonyl group numbering (locant) priity is given to the carbonyl carbon aldehydes always have the carbonyl group at carbon 1, so a number is not needed ketones have the "one" suffix, aldehydes have the "al" suffix Br Br C 2. eview of the Synthesis of Aldehydes and Ketones Problems: 5 A. Friedel-Crafts Acylation Cl AlCl 3 B. xidation of Alcohols (most common method) PCC KMn 4 K 2 Cr 2 7, 2 S 4, 2
2 3. eview of eactions of Aldehydes and Ketones A. xidation of Aldehydes PCC KMn 4 K 2 Cr 2 7, 2 S 4, 2 2 in air (slowly) KMn 4 K 2 Cr 2 7, 2 S 4, 2 aldehydes may be oxidized using KMn 4 Jones reagent to the carboxylic acid since aldehydes are usually synthesized via oxidation of 1 alcohols, the synthesis of carboxylic acids is usually accomplished via direct oxidation of 1 alcohols with the strong oxidizing agents ketones CANNT be oxidized further B. eduction of Aldehydes and Ketones Zn(g), Cl N 2 4, K, heat Zn(g), Cl N 2 4, K, heat Clemmensen Wolff-Kishner reduction of aldehydes and ketones leads to reduction of the carbonyl group to a C 2 group 2, Pt 2, Pd hydrogenation of ketones fms 2 alcohols (the opposite reaction of the oxidation process) hydrogenation of aldehydes fms 1 alcohols Problems: 6 4. eactivity of Aldehydes and Ketones '() ' both aldehydes and ketones have partial positive charge at the carbon of the carbonyl group due to the polar C= bond the partial charge on the aldehyde is greater since it is flanked by a single electron-donating alkyl group while both aldehydes and ketones are reactive towards nucleophilic addition, aldehydes are me reactive due to i) the greater partial positive charge and ii) less steric interference
3 5. Mode of Attack of Strong Nucleophiles on the Carbonyl Group of Aldehydes and Ketones Nu Nu Nu ()' ()' ()' nucleophiles attack the partially positively charged carbon of the carbonyl group by pushing electrons into the polarized pi bond the pi electrons are fced onto the electronegative oxygen atom these reactions are often followed up by addition of acidic water (Cl, ) to protonate the negatively charged oxygen and fm a neutral product 6. Addition of Strong Nucleophiles to Aldehydes and Ketones A. Addition of rganometallic eagents NaN C 3 C 2 Li C 1. C 3 MgBr ? these types of nucleophilic additions to aldehydes and ketones are critical reactions since they result in the fmation of NEW C-C bonds! these reactions, therefe, provide a way in which to create larger molecules from readily available smaller molecules Problems: 7
4 B. Addition of CN 1. NaCN CN catalytic NaCN there are two methods f addition of CN to a carbonyl group. The net result is the same the product of addition is referred to as a "cyanohydrin" to reflect the presence of both the cyanide AND hydroxyl groups as with the ganometallics, this reaction fms a new C-C bond C. Addition of ydride (hydride reduction) hydride Na sodium hydride 3 C ' a "hydride" is a hydrogen with an extra electron, giving it a negative charge sodium hydride is the simplest fm of hydride, but in this fm it acts only as a strong base and never as a nucleophile NaB 4 and LiAl 4 are both sources of nucleophilic hydride Na B Li Al NaB 4 sodium bohydride Examples LiAl 4 (LA) lithium aluminum hydride 1. NaB LiAl 4 2. Cl, 2 reduction of aldehydes with either NaB 4 LiAl 4 results in the fmation of 1 alcohols reduction of ketones with either NaB 4 LiAl 4 results in the fmation of 2 alcohols
5 Summary of Nucleophilic Addition eactions of Aldehydes and Ketones '() nu product nucleophile catalyst type of product (hydride, NaB 4 LiAl 4 ) none alcohol (1 from aldehyde, 2 from ketone) '() (Grignard, alkyllithium) none alcohol (2 from aldehyde, 3 from ketone) '() C N (cyanide) none cyanohydrin NC '() D. Addition of Alcohols '() '() + '() alkoxides are strong nucleophiles but alcohols are po nucleophiles alcohols will not react with aldehydes ketones in the absence of an acid catalyst an acid catalyst protonates a lone pair of the oxygen atom of the carbonyl group protonation increases the partial positive charge on the carbon and enhances the reactivity of the carbonyl towards nucleophilic addition under acidic conditions, aldehydes and ketones will react with the weaker alcohol nucleophile the most common acid catalysts are 3 P 4, 2 S 4, Cl paratoluenesulfonic acid (Ts) '() '() unprotonated '() protonated C 3 cat. 2 S 4 Et Ts cat. 2 S 4 reaction of aldehydes ketones with alcohols under acid catalysis results in the addition of TW equivalents of the alcohol to the carbonyl group. Τthe product is called a "ketal" if a diol such as ethylene glycol is used, both ends of the diol add across the carbonyl group to fm a cyclic ketal cyclic ketals are the most often utilized type of ketal
6 Ts ketals are "ether-like" compounds that behave like ethers, i.e., they are fairly unreactive the ketal fmation process can be reversed by addition of water under acidic conditions ketals act as carbonyl "protecting groups" in that they can be placed on a carbonyl group to keep it from reacting and then removed when desired C 3 1 equivalent NaB 4 C 3 2 equivalents NaB 4 C 3 Glucose, Sbitol and other Sweeteners sbitol glucose α-d-glucose (hemiacetal) Sucrose (table sugar) Cl Cl Sucralose (Splenda ) Cl N S Saccharin (Sweet 'N Low ) C 2 Stevia (Truvia )
7 7. Addition/Elimination eactions of Aldehydes and Ketones A. The Wittig eaction '() verall eaction: (Ph) 3 P C ' C ' '() the Wittig reaction takes place between an aldehyde a ketone and a Wittig reagent the final product is replacement of the C= double bond by a C=C double bond (Ph) 3 P C 2 (Ph) 3 P C 2 eaction Steps 3 C C 3 (Ph) 3 P C 3 3 C C 3 (Ph) 3 P 3 C C 3 C C 3 C 3 C 3 C C 3 (Ph) 3 P (Ph) 3 P CC 3 Examples (Ph) 3 P=CC 2 C 3 C P(Ph) 3
8 B. Imine Fmation verall eaction: '() 2 N + N '() an imine when a 1 amine reacts with a ketone aldehyde, an imine product results an acid catalyst [usually Ts Cl] is often needed the final product is replacement of the C= double bond by a C=N double bond eaction Steps C 3 N 2 3 C C C C 3 Examples N Ph C 3 C 2 N 2 Ts Ts enzyme trans-retinal cis-retinal enzyme Protein N 2 Protein N LIGT Protein N
9 Summary of Nucleophilic Addition eactions of Aldehydes and Ketones '() nu product nucleophile catalyst type of product single addition reactions (hydride, NaB 4 LiAl 4 ) none alcohol (1 from aldehyde, 2 from ketone) '() (Grignard, alkyllithium) none alcohol (2 from aldehyde, 3 from ketone) '() (ganocuprate) none Michael addition to α,β-unsaturated aldehydes and ketones C N (cyanide) none cyanohydrin NC '() double addition reactions (alcohols) + acetal '() addition-elimination reactions (Ph) 3 P=C 2 (Wittig reagents) none alkene C '() -N 2 (1 amine) + sometimes imine N '()
Chapter 20: Aldehydes and Ketones
hapter 20: Aldehydes and Ketones [hapter 20 Sections: 20.1-20.7, 20.9-10.10, 20.13] 1. Nomenclature of Aldehydes and Ketones ketone ' aldehyde 2. eview of the Synthesis of Aldehydes and Ketones Br Br f
More informationAldehydes 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.
More informationLoudon Chapter 19 Review: Aldehydes and Ketones CHEM 3331, Jacquie Richardson, Fall Page 1
Loudon Chapter 19 eview: Aldehydes and Ketones CEM 3331, Jacquie ichardson, Fall 2010 - Page 1 Beginning with this chapter, we re looking at a very important functional group: the carbonyl. We ve seen
More informationChapter 17: Carbonyl Compounds II
Chapter 17: Carbonyl Compounds II Learning bjectives: 1. ecognize and assign names to aldehydes and ketones. 2. Write the mechanism for nucleophilic addition and nucleophilic addition-elimination reactions
More informationChapter 12: Carbonyl Compounds II
Chapter 12: Carbonyl Compounds II Learning bjectives: 1. Recognize and assign names to aldehydes and ketones. 2. Write the mechanism for nucleophilic addition and nucleophilic addition-elimination reactions
More informationLecture 15. More Carbonyl Chemistry. Alcohols React with Aldehydes and Ketones in two steps first O R'OH, H + OR" 2R"OH R + H 2 O OR" 3/8/16
Lecture 15 More Carbonyl Chemistry R" R C + R' 2R" R C R" R' + 2 March 8, 2016 Alcohols React with Aldehydes and Ketones in two steps first R', + R R 1 emiacetal reacts further in acid to yield an acetal
More informationChapter 18: Carbonyl Compounds II
Chapter 18: Carbonyl Compounds II Learning bjectives: 1. ecognize and assign names to aldehydes and ketones. 2. Write the mechanism for nucleophilic addition and nucleophilic addition-elimination reactions
More informationChapter 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;
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 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 informationLecture 18. Oxidation and Reduction. Oxidation. Reduction O CH 4 CH 3 OH H C H. Chemistry 328N
Lecture 18 xidation and Reduction C 4 C 3 C C C xidation Reduction March 27, 2018 Suppose you want to make this compound????? C + BrC 2 C 2 C?? CC 2 C 2 C 4-ydroxy-4-phenylbutanal It s an alcohol. Use
More informationChapter 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
More informationBasic 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
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 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 17 Aldehydes and Ketones
hapter 17 Aldehydes and Ketones arbonyl Groups polarized (1) Aldehydes and Ketones ' aldehydes ketones : and : are poor leaving groups (2) arboxylic Acid Derivatives l ' ' 2 carboxylic acid substituent
More informationTopic 9. Aldehydes & Ketones
Chemistry 2213a Fall 2012 Western University Topic 9. Aldehydes & Ketones A. Structure and Nomenclature The carbonyl group is present in aldehydes and ketones and is the most important group in bio-organic
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 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 informationAldehydes and Ketones
Aldehydes and Ketones Preparation of Aldehydes xidation of Primary Alcohols --- 2 P 1o alcohol ydroboration of a Terminal Alkyne, followed by Tautomerization --- 1. B 3, TF 2. 2 2, K 2 terminal alkyne
More information12. Aldehydes & Ketones (text )
2009, Department of Chemistry, The University of Western ntario 12.1 12. Aldehydes & Ketones (text 13.1 13.11) A. Structure and Nomenclature The carbonyl group is present in aldehydes and ketones and is
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 informationSynthesis of Nitriles a. dehydration of 1 amides using POCl 3 : b. SN2 reaction of cyanide ion on halides:
I. Nitriles Nitriles consist of the CN functional group, and are linear with sp hybridization on C and N. Nitriles are non-basic at nitrogen, since the lone pair exists in an sp orbital (50% s character
More informationAldehydes & Ketones I
2302272 Org Chem II Part I Lecture 3 Aldehydes & Ketones I Instructor: Dr. Tanatorn Khotavivattana E-mail: tanatorn.k@chula.ac.th Recommended Textbook: Chapter 18 in Organic Chemistry, 8 th Edition, L.
More informationChem 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
More informationChapter 18 Ketones and Aldehydes
Chapter 18 Ketones and Aldehydes omenclature o Ketones have priority over alcohols Find the longest chain with the carbonyl in it. ame the parent and replace the e with one Say where the carbonyl is. octan-3-one
More informationTopic 4 Aldehydes and Ketones
4-1 Topic 4 Aldehydes and Ketones 16.1 4-2 Aldehydes and Ketones ' aldehyde ketone The polarized oxygen-carbon -bond renders aldehydes and ketones electrophilic: ' The electrophilicity of the oxygen-carbon
More informationacetaldehyde (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)
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 informationAldehydes and Ketones
9 Aldehydes and Ketones hapter Summary The carbonyl group, =, is present in both aldehydes (=) and ketones ( 2 =). The IUPA ending for naming aldehydes is -al, and numbering begins with the carbonyl carbon.
More informationCarbonyls (Ch ketones and aldehydes and carboxylic acids derivatives)
arbonyls (h 16-19 ketones and aldehydes and carboxylic acids derivatives) +δ -δ ' - sp 2 - trigonal planar (120 0 ) - strongly polarized double bond eactivity? addition nucleophilic 1 Nucleophilic Addition
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 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 informationChem 263 Nov 3, 2016
hem 263 Nov 3, 2016 Preparation of Aldehydes from Acid alides? + l l acid chloride aka acyl chloride aldehyde Needed: 2 Actual eagents: 2 /Pd Al This is lithium tri-t-butoxy aluminum hydride, a very sterically
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 informationIntroduction & 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
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 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 informationChapter 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
More informationChapter 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.
More information1- Reaction at the carbonyl carbon (Nucleophilic addition reactions).
Reactions of aldehydes and Ketones Aldehydes and Ketones undergo many reactions to give a wide variety of useful derivatives. There are two general kinds of reactions that aldehydes and ketones undergo:
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 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 informationSynthetic possibilities Chem 315 Beauchamp 1
Synthetic possibilities hem Beauchamp Propose reasonable syntheses f the following target molecules (TM-#). You can use the given starting materials and any typical ganic reagents studied in our course
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 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 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 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 informationCHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Final Exam December 15, 2010 Your name: ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This test contains 15 pages Time: 2h 30 min 1. / 16 2. / 15 3. / 24
More 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 informationCH 19: Aldehydes and Ketones
rganic hemistry otes by Jim Maxka 19: Aldehydes and Ketones Topics aming, structure, and properties Formation of = eactions with weak nucleophiles: and Derivatives: imines and enamines. eactions with strong
More informationWeek 6 notes CHEM
Week 6 notes EM1002 2009 Unless otherwise stated, all images in this file have been reproduced from: Blackman, Bottle, Schmid, Mocerino and Wille, hemistry, 2007 (John Wiley) ISBN: 9 78047081 0866 1 Note
More information2.222 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
More informationLoudon Chapter 20 & 21 Review: Carboxylic Acids & Derivatives CHEM 3331, Jacquie Richardson, Fall Page 1
Loudon Chapter 20 & 21 eview: Carboxylic Acids & Derivatives CEM 3331, Jacquie ichardson, Fall 2010 - Page 1 These two chapters cover compounds which are all at the three bonds to more electronegative
More informationStructure and Reactivity: Prerequired Knowledge
Structure and eactivity: Prerequired Knowledge!!! The concepts presented in this summary are required for lecture and examination!!! 1. Important Principles in rganic Chemistry In general, structures which
More information18.8 Oxidation. Oxidation by silver ion requires an alkaline medium
18.8 Oxidation Oxidation by silver ion requires an alkaline medium Test for detecting aldehydes Tollens reagent to prevent precipitation of the insoluble silver oxide, a complexing agent is added: ammonia
More informationChapter 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
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 informationp Bonds as Electrophiles
Chapter 7 p Bonds as Electrophiles REACTIONS OF CARBONYLS AND RELATED FUNCTIONAL GROUPS Copyright 2018 by Nelson Education Limited 1 7.2.1 Orbital structure of the carbonyl group Because oxygen is more
More informationChem 263 Nov 24, Properties of Carboxylic Acids
Chem 263 ov 24, 2009 Properties of Carboxylic Acids Since carboxylic acids are structurally related to both ketones and aldehydes, we would expect to see some similar structural properties. The carbonyl
More informationChem 263 Nov 14, e.g.: Fill the reagents to finish the reactions (only inorganic reagents)
hem 263 ov 14, 2013 More examples: e.g.: Fill the reagents to finish the reactions (only inorganic reagents) Br 2 hv Br a 2 r 4 S 2 or swern oxidation Mg Li 0 0 MgBr Li e.g. : Fill the reagents (any reagents
More informationCarbonyl Chemistry IV + C O C. Lecture 10. Chemistry /30/02
arbonyl hemistry IV Ō - + Lecture 10 Addition of Nitrogen Nucleophiles Primary Amines RN 2 Imines Secondary Amines R 2 N Enamines ydrazine derivatives RNN 2 ydrazones ydroxyl Amine N 2 ximes Imine Formation
More informationTOPIC 3 - ALDEHYDES AND KETONES (Chapters 12 & 16)
TPIC 3 - ALDEYDES AND KETNES (Chapters 12 & 16) Lecture 15 Web12 12.1 Introduction 16.1 Introduction 16.2 Nomenclature of Aldehydes and Ketones 16.3 ysical Properties 12.2 xidation Reduction Reactions
More informationCarbonyl 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-
More informationCHEMISTRY 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
More informationLearning 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
More informationALDEHYDES AND KETONES
11 R R R ALDEYDES AND KETNES APTER SUMMARY 111 Structure of Aldehydes and Ketones Aldehydes and ketones both have a carbonyl group (carbonoxygen double bond); aldehydes have at least one carbon bonded
More informationC h a p t e r T w e n t y: Aldehydes and Ketones
C h a p t e r T w e n t y: Aldehydes and Ketones (S)-Warfarin (named for the Wisconsin Alumni Research Foundation), a useful clinical anticoagulant which as a racemate is also a rat poison Note: Problems
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 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 informationChapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions
Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry s Organic
More informationCHEM 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.
More informationFirst Year Organic Chemistry THE CHEMISTRY OF THE CARBONYL GROUP: CORE CARBONYL CHEMISTRY
First Year rganic Chemistry TE CEMISTY F TE CABNYL GUP: CE CABNYL CEMISTY Professor Tim Donohoe 8 lectures, T, weeks 1-4, 2015 Wednesdays at 9am; Fridays at 10am (Dyson Perrins) andout A You will be able
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 informationChem 263 March 28, 2006
Chem 263 March 28, 2006 Properties of Carboxylic Acids Since carboxylic acids are structurally related to both ketones and aldehydes, we would expect to see some similar structural properties. The carbonyl
More informationAldehydes, Ketones and Carboxylic acids
Teacher Orientation Aldehydes, Ketones and Carboxylic Acids contains following topics: Nomenclature Preparation Properties Student Orientation Preparation and Properties Of Aldehydes, Ketones and Carboxylic
More informationChapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions
Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry s Organic
More informationReversible Additions to carbonyls: Weak Nucleophiles Relative Reactivity of carbonyls: Hydration of Ketones and Aldehydes
Reversible Additions to carbonyls: Weak Nucleophiles Weak nucleophiles, such as water, alcohols, and amines, require acid or base catalysis to undergo addition to carbonyl compounds Relative Reactivity
More informationChapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions. Naming Aldehydes. - aldehyde. - ketone
hapter 19 Aldehydes and Ketones: Nucleophilic Addition eactions - aldehyde - substance that has an organic group () bonded to functionality () - ketone methanol catalyst heat - substance that has two organic
More informationFIRST EXAMINATION. Name: CHM 332
ame: CM 332 FIRST EXAMIATI All answers should be written on the exam in the spaces provided. Clearly indicate your answers in the spaces provided; if I have to guess as to what or where your answer is,
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 informationChapter 11 Reaction of Alcohols
Chapter 11 eaction of Alcohols xidation of alcohols Alcohols are at the same oxidation level as alkenes Therefore alkenes can be converted to alcohols with acidic water PDC or PCC 2 C C 2 3 + X 3 C 3 C
More information18.10 Conjugate Additions O O. O X BrCH 2 CH 2 CH 2 CCH 3 ± ± BrCH 2 CH 2 CH 2 CH 3. TsOH 1 O C O O W 3 CH 3 CCH 3 CH 3 CCH 2 CH 2 CH 2 CH 3
80 NJUGATE ADDITINS 779 An attempt to form a Grignard reagent from 5-bromo- 2-pentanone is doomed to failure because the Grignard will react with the carbonyl group Therefore, the carbonyl group is first
More informationCHEM 203. Final Exam December 18, 2013 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Your name: Final Exam December 18, 2013 ANSWERS 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.
More informationLecture 19. Carboxylic Acids O C OH O R C O - + H + O - Chemistry 328N
Lecture 19 arboxylic Acids R R - + + R - March 29, 2018 Review: Selectivity in Reduction LiAl 4 reduces any and all carbonyl compounds to the corresponding alcohols NaB 4 only reduces aldehydes and ketone
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 informationSummary of Alcohol Syntheses, Ch. 10 (and Review of Old Ones).
Chem 350 Jasperse Ch. 10 Notes 1 Summary of Alcohol Syntheses, Ch. 10 (and eview of ld nes). 1 Na Na Potassium (K) analogous. Key way to convert alcohol to alkoxide, reactive as S N 2 nucleophile and E2
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 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 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 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 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 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 informationKetones and Aldehydes
Ketones and Aldehydes Adapted from rganic hemistry, L. G. Wade, Jr. = 1 Violet (Irone) salicylaldehyde (meadowsweet) 3 ( 2 ) 4 (Eucalyptus) 3 ( 2 ) 10 (itrus Fruits) Piperonal (eliotrope) 3 3 Raspberries
More informationOrganic Chemistry, Third Edition. Janice Gorzynski Smith University of Hawai i. Chapter 21. Aldehydes and Ketones Nucleophilic Addition
Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai i Chapter 21 Aldehydes and Ketones Nucleophilic Addition Prepared by Rabi Ann Musah State University of New York at Albany Copyright
More informationElectrophile = 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
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 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 informationCarbonyl Compounds. Introduction
Carbonyl Compounds Introduction 1 Introduction Two broad classes of compounds contain the carbonyl group: [1] Compounds that have only carbon and hydrogen atoms bonded to the carbonyl [2] Compounds that
More informationNucleophilic Addition Reactions of Carboxylic Acid Derivatives
Lecture 5: bjectives: Nucleophilic Addition eactions of Carboxylic Acid Derivatives By the end of this lecture you will be able to: draw the mechanism of a nucleophilic addition-elimination reaction with
More information