Lecture 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

Size: px
Start display at page:

Download "Lecture 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"

Transcription

1 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

2 emiacetal reacts further in acid to yield an acetal R R', + R R' Example + Cl 2

3 Diols Form + catalyst Note that EVERY step is an equilibrium Therefore, the reaction can be pushed forward or backward by appropriate choice of conditions The forward reaction is synthesis The backward reaction is hydrolysis 3

4 ydrolysis of Acetals R' R2 2, + R 1 R' mechanism: reverse of acetal formation hemiacetal is intermediate. application: aldehydes and ketones can be "protected" as acetals. 4

5 ydrolysis 3 + Suppose you want to make this compound? + Br??? 5-ydroxy-5-phenylpentanal It s an alcohol. Use the Grignard Reaction!! So you got a problem with this plan????? Secret is.acetals as protecting Groups 5

6 Acetals as Protecting Groups l If the Grignard reagent were prepared from 3-bromopropanal, it would self-destruct! l First protect the -C group as an acetal Br + catalyst Br + 2 Acetals as Protecting Groups l Then do the Grignard reaction Br Mg, TF BrMg 3 + MgBr ydrolysis in dilute acid gives the desired product 6

7 For example, the conversion shown cannot be carried out directly..why? 1. NaN 2 C 3 CC 2 C 2 C C 2. C 3 I C 3 CC 2 C 2 C C-C 3 C 3 CC 2 C 2 C C: because the carbonyl group and the carbanion are incompatible. Strategy 1) protect C= 2) alkylate 3) restore C= 7

8 Protect C 3 CC 2 C 2 C C + C 2 C 2 benzene 2 S 4, Cat. Alkylate 2 C C 2 C C 3 C 2 C 2 C C 1. NaN 2 2. C 3 I 8

9 2 C C 2 Deprotect C C C 2 C 2 C CC Cl Synthesis! Starting from benzene, cyclohexanone, and molecules with 3 carbons or less, synthesize the following molecule: C 3 C 9

10 xidation and Reduction l Aldehydes are oxidized to carboxylic acids by a variety of oxidizing agents and it is possible to do some selective reduction reactions C 4 C 3 C xidation Reduction C C Reduction l Aldehydes can be reduced to 1 alcohols and ketones to 2 alcohols. In addition, the C= group can be reduced to a -C 2 - group Aldehydes RC Can be Reduced to RC 2 RC 3 Ketones RCR' Can be Reduced to RCR' RC 2 R' 10

11 Metal ydride Reduction l The most selective reagents for the reduction of aldehydes and ketones are NaB 4 and LiAl 4 both are sources of hydride ion, : -, a very powerful nucleophile Na + -B- Sodium borohydride Li + -Al- L ithium aluminum hydride (LA) ydride ion NaB 4 Reduction l The key step in metal hydride reduction is transfer of a hydride ion to the C= group to form a tetrahedral carbonyl addition compound B R C R 11

12 Closer look at borohydride reductions B- bond is much stronger than B Bond This is the driving force for the reaction NaB 4 Reduction l Reductions with NaB 4 are most commonly carried out in aqueous methanol, in pure methanol, or in ethanol R C + N a B 4 C 3 12

13 Examples: Sodium Borohydride Aldehyde 2 N Ketone C NaB 4 methanol NaB 4 ethanol Lithium aluminum hydride LiAl 4 l More reactive than sodium borohydride l Cannot use water, ethanol, methanol etc., as solvents l Diethyl ether and TF are the most commonly used solvent l This is a dangerous but useful reagent R C 2 C C 3 1 ) T F + L i A l 4 2 ) 3 + R C 2 C C 3 13

14 Aldehyde Examples: Lithium Aluminum ydride C 3 (C 2 ) 5 C 1. LiAl 4 diethyl ether 2. 2 Ketone (C 6 5 ) 2 CCC 3 1. LiAl 4 diethyl ether 2. 2 Selectivity neither NaB 4 or LiAl 4 will reduce isolated double bonds 1. LiAl 4 diethyl ether

15 Selectivity in Reduction l LiAl 4 reduces any and all carbonyl compounds to the corresponding alcohols l NaB 4 only reduces aldehydes and ketone Catalytic Reduction l Catalytic reductions are generally carried out from 25 to 100 C and from 1 to 5 atm 2 l Carbon-carbon double bonds can be selectively reduced using Rhodium catalysts 2 /Rh NaB 4 Me 15

16 ydrogenolysis of benzylic carbonyls Palladium catalysis of hydrogenation reduces only benzylic C- bonds to methylene groups. Benzyl ethers, aldehydes and alcohols are also reduced to the corresponding methylene group 2, P d / C 2, P d / C 16

Lecture 18. Oxidation and Reduction. Oxidation. Reduction O CH 4 CH 3 OH H C H. Chemistry 328N

Lecture 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 information

Still More Carbonyl Chemistry

Still More Carbonyl Chemistry Lecture 17 Still More arbonyl hemistry ' ' A B P( 6 5 ) 3 A P( 6 5 ) 3 B March 22, 2018 eaction Theme The most common reaction of a carbonyl group is addition of a nucleophile to form a tetrahedral addition

More information

Chapter 12: Carbonyl Compounds II

Chapter 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 information

Aldehydes and Ketones Reactions. Dr. Sapna Gupta

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.

More information

Carbonyl Chemistry IV + C O C. Lecture 10. Chemistry /30/02

Carbonyl 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 information

Chapter 20: Aldehydes and Ketones

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

More information

Chapter 20: Aldehydes and Ketones

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 information

b.p.=100 C b.p.=65 C b.p.=-25 C µ=1.69 D µ=2.0 D µ=1.3 D

b.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 information

Lecture 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; 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 information

Chem 263 March 7, 2006

Chem 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 information

Carbonyls (Ch ketones and aldehydes and carboxylic acids derivatives)

Carbonyls (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 information

Chapter 12. Alcohols from Carbonyl Compounds Oxidation-Reduction & Organometallic Compounds. Structure

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

More information

Lecture 19. Carboxylic Acids O C OH O R C O - + H + O - Chemistry 328N

Lecture 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 information

ALDEHYDES AND KETONES

ALDEHYDES 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 information

Alcohol Synthesis. Dr. Sapna Gupta

Alcohol 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 information

18.10 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

18.10 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 information

Carbonyl Chemistry. aldehydes ketones. carboxylic acid and derivatives. Wednesday, April 29, 2009

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-

More information

Loudon Chapter 19 Review: Aldehydes and Ketones CHEM 3331, Jacquie Richardson, Fall Page 1

Loudon 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 information

CARBONYL COMPOUNDS: OXIDATION-REDUCTION REACTION

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

More information

Basic Organic Chemistry

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

More information

DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE

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,

More information

18.8 Oxidation. Oxidation by silver ion requires an alkaline medium

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

More information

Chem 263 Notes March 2, 2006

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

More information

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.

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

More information

Chapter 18: Ketones and Aldehydes. I. Introduction

Chapter 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 information

Chapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds

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

More information

acetaldehyde (ethanal)

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)

More information

Chem 263 Nov 7, elimination reaction. There are many reagents that can be used for this reaction. Only three are given in this course:

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

More information

LECTURE #22 Thurs., Nov.15, 2007

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

More information

CHEMISTRY Topic #8: Oxidation and Reduction Reactions Fall 2018 Dr. Susan Findlay

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

More information

Chapter 18 Ketones and Aldehydes. Carbonyl Compounds. Chapter 18: Aldehydes and Ketones Slide 18-2

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.

More information

CHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models

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

More information

Chem 263 Nov 3, 2016

Chem 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 information

Chapter 20 Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution

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

More information

Chapter 17: Alcohols and Phenols

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

More information

Physical Properties. Alcohols can be: CH CH 2 OH CH 2 CH 3 C OH CH 3. Secondary alcohol. Primary alcohol. Tertiary alcohol

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

More information

Chapter 18: Carbonyl Compounds II

Chapter 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 information

Chem 263 Nov 24, Properties of Carboxylic Acids

Chem 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 information

Synthesis 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. 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 information

Suggested solutions for Chapter 6

Suggested solutions for Chapter 6 s for Chapter 6 6 PRBLEM 1 Draw mechanisms for these reactions: NaB 4 Et, 2 1. LiAl 4 C 2. 2 Rehearsal of a simple but important mechanism that works for all aldehydes and ketones. Draw out the B 4 and

More information

Topic 9. Aldehydes & Ketones

Topic 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 information

Reduction. Boron based reagents. NaBH 4 / NiCl 2. Uses: Zn(BH 4 ) 2. Preparation: Good for base sensitive groups Chelation control model.

Reduction. Boron based reagents. NaBH 4 / NiCl 2. Uses: Zn(BH 4 ) 2. Preparation: Good for base sensitive groups Chelation control model. Uses: Ar N 2 Ar N 2 Ar N Ar N 2 eduction Boron based reagents NaB 4 / NiCl 2 2 Ar C N Ar C N 2 Preparation: Zn(B 4 ) 2 ZnCl 2 (Ether) NaB 4 Zn(B 4 ) 2 Good for base sensitive groups Chelation control model

More information

ALCOHOLS: Properties & Preparation

ALCOHOLS: 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 information

EWG EWG EWG EDG EDG EDG

EWG EWG EWG EDG EDG EDG Functional Group Interconversions Lecture 4 2.1 rganic Synthesis A. Armstrong 20032004 3.4 eduction of aromatic systems We can reduce aromatic systems to cyclohexanes under very forcing hydrogenolytic

More information

Introduction & Definitions Catalytic Hydrogenations Dissolving Metal Reduction Reduction by Addition of H- and H+ Oxidation of Alcohols Oxidation of

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

More information

Aldehydes and Ketones

Aldehydes 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 information

Aldehydes and Ketones

Aldehydes 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 information

TOPIC 3 - ALDEHYDES AND KETONES (Chapters 12 & 16)

TOPIC 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 information

CHEM 345 Problem Set 07 Key

CHEM 345 Problem Set 07 Key CHEM 345 Problem Set 07 Key 1.) Fill in the appropriate reaction arrow. The starting material is on the left, the product is on the right. Use. Simple Ring Size. 5 and 6 are favored. 3 is not. That s it.

More information

Chapter 20: Aldehydes and Ketones

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;

More information

Synthesis of Nitriles a. dehydration of 1 amides using POCl 3 : b. SN2 reaction of cyanide ion on halides:

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

More information

Chapter 17: Carbonyl Compounds II

Chapter 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 information

Carboxylic Acids O R C + H + O - Chemistry 618B

Carboxylic 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 information

c. Oxidizing agent shown here oxidizes 2º alcohols to ketones and 1º alcohols to carboxylic acids. 3º alcohols DO NOT REACT.

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

More information

ORGANIC - CLUTCH CH ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION

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

More information

p Bonds as Electrophiles

p 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 information

Name Department of Chemistry SUNY/Oneonta. Chem Organic Chemistry II Examination #2 - March 12, 2001

Name Department of Chemistry SUNY/Oneonta. Chem Organic Chemistry II Examination #2 - March 12, 2001 Name Department of hemistry SUNY/neonta hem 322 - rganic hemistry II Examination #2 - March 12, 2001 INSTRUTINS This examination has two parts. Part I is in multiple choice format and the answers should

More information

I. Write Structures for the compounds named below: (12 points) H 2 N NH 2. Acetone Hydrazine Cyclohexane carbaldehyde H 3 C

I. Write Structures for the compounds named below: (12 points) H 2 N NH 2. Acetone Hydrazine Cyclohexane carbaldehyde H 3 C I. Write Structures for the compounds named below: (12 points) 3 2 N N 2 Acetone ydrazine yclohexane carbaldehyde N P( 6 5 ) 3 3 An ethyl ylide of Any imine 3-xo-6-phenylhexanal triphenylphosphine II.

More information

Learning Guide for Chapter 15 - Alcohols (II)

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

More information

Week 6 notes CHEM

Week 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 information

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

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

More information

Carbonyls. Aldehydes and Ketones N Goalby chemrevise.org. chemrevise.org

Carbonyls. Aldehydes and Ketones N Goalby chemrevise.org. chemrevise.org arbonyls Aldehydes and Ketones N Goalby chemrevise.org arbonyls are compounds with a = bond, they can be either aldehydes or ketones. 3 ethanal 3 3 propanone If the = is on the end of the chain with an

More information

C 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 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 information

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!

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

More information

CHEM 203. Final Exam December 18, This a closed-notes, closed-book exam. You may use your set of molecular models

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.

More information

Chapter 9 Aldehydes and Ketones Excluded Sections:

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

More information

Chapter 10: Carboxylic Acids and Their Derivatives

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

More information

Carbonyl Group in Aldehydes and Ketones

Carbonyl Group in Aldehydes and Ketones Lecture 4: Aldehydes, Ketones, and Chiral Molecules 14.1 Aldehydes and Ketones Carbonyl Group in Aldehydes and Ketones A carbonyl group (C=) In an aldehyde is attached to at least one atom. In a ketone

More information

12. Aldehydes & Ketones (text )

12. 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 information

The Organic Acids. Carboxylic Acids * *

The Organic Acids. Carboxylic Acids * * arboxylic Acids The rganic Acids Some Notation: Acids and their conjugate bases pka ~ 15 - weak acid arboxylic Acid pka ~ 4 moderate acid - arboxylate Anion pka ~ -7 very strong acid l - l arboxylic acids

More information

Chapter 14 Aldehydes and Ketones: Addition Reactions at Electrophilic Carbons Overview of Chapter Structures of aldehydes and ketones

Chapter 14 Aldehydes and Ketones: Addition Reactions at Electrophilic Carbons Overview of Chapter Structures of aldehydes and ketones hem 215 F12 otes Dr. Masato Koreeda - Page 1 of 11. Date: September 19, 2012 hapter 14 Aldehydes and Ketones: Addition eactions at Electrophilic arbons verview of hapter 14 1. Structures of aldehydes and

More information

ORGANIC - BROWN 8E CH ALDEHYDES AND KETONES.

ORGANIC - 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 information

Reversible Additions to carbonyls: Weak Nucleophiles Relative Reactivity of carbonyls: Hydration of Ketones and Aldehydes

Reversible 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 information

DAMIETTA UNIVERSITY. Energy Diagram of One-Step Exothermic Reaction

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

More information

Chapter 8: Ethers and Epoxides. Diethyl ether in starting fluid

Chapter 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 information

I N V E S T I C E D O R O Z V O J E V Z D Ě L Á V Á N Í CARBONYL COMPOUNDS

I N V E S T I C E D O R O Z V O J E V Z D Ě L Á V Á N Í CARBONYL COMPOUNDS = substances containing the carbonyl group Aldehydes have the C=O group at the end of the chain, the aldehydic group is then... Naming of aldehydes: In the systematic name there is a suffix after the stem

More information

CHAPTER 20 HW: CARBONYL REDOX RXNS

CHAPTER 20 HW: CARBONYL REDOX RXNS APTER 20 W: ARBNYL REDX RXNS YDRIDE REATIN MEANISM 1. Give the curved arrow mechanism for each reaction. LiAl 4 NaB 4 3 2 YDRIDE REATINS 2. Give the major organic product(s) for each reaction. Indicate

More information

CHAPTER 20: MORE ABOUT OXIDATION REDUCTION REACTIONS Oxidation Reduction Reactions of Organic Compounds: An Overview

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,

More information

A. B. C. D. 2. Which compound does not give a stable Grignard reagent when reacting with Mg metal?

A. B. C. D. 2. Which compound does not give a stable Grignard reagent when reacting with Mg metal? Practice Test, Chemistry 2220 Final Exam 1. Which structure has the MST signals for its proton NMR? 2. Which compound does not give a stable Grignard reagent when reacting with Mg metal? 3. Which of these

More information

Chapter 17 Aldehydes and Ketones

Chapter 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 information

CARBOXYLIC ACIDS AND THEIR DERIVATIVES. 3. Predict the relative acidity and basicity of compounds and ions. Important criteria include:

CARBOXYLIC ACIDS AND THEIR DERIVATIVES. 3. Predict the relative acidity and basicity of compounds and ions. Important criteria include: CARBXYLIC ACIDS AND TEIR DERIVATIVES A STUDENT SULD BE ABLE T: 1. Give the IUPAC name given the structure, and draw the structure given the name, of carboxylic acids and their metal salts, acyl chlorides,

More information

Chap 11. Carbonyl Alpha-Substitution Reactions and Condensation Reactions

Chap 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

Loudon Chapter 20 & 21 Review: Carboxylic Acids & Derivatives CHEM 3331, Jacquie Richardson, Fall Page 1

Loudon 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 information

CARBOXYLIC ACIDS AND THEIR DERIVATIVES

CARBOXYLIC ACIDS AND THEIR DERIVATIVES ARBXYLI AIDS AND TEIR DERIVATIVES A STUDENT SULD BE ABLE T: 1. Give the IUPA name given the structure, and draw the structure given the name, of carboxylic acids and their metal salts, acyl chlorides,

More information

Additions to the Carbonyl Groups

Additions to the Carbonyl Groups Chapter 18 Additions to the Carbonyl Groups Nucleophilic substitution (S N 2andS N 1) reaction occurs at sp3 hybridized carbons with electronegative leaving groups Why? The carbon is electrophilic! Addition

More information

Chem 263 March 28, 2006

Chem 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 information

Chemistry 234 Practice Exam 3. The Periodic Table

Chemistry 234 Practice Exam 3. The Periodic Table ame: Last First MI Chemistry 234 Practice Exam 3 Instructions: The first 15 questions of this exam should be answered on the provided Scantron. You must use a pencil for filling in the Scantron sheet.

More information

Structure and Reactivity: Prerequired Knowledge

Structure 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 information

ALCOHOLS AND PHENOLS

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 information

Chapter 8 Alkenes and Alkynes II: Addition Reactions "

Chapter 8 Alkenes and Alkynes II: Addition Reactions Chapter 8 Alkenes and Alkynes II: Addition Reactions Additions to Alkenes Generally the reaction is exothermic because one π and one σ bond are converted to two σ bonds Alkenes are electron rich The π

More information

HW #5: 16.20, 16.28, 16.30, 16.32, 16.40, 16.44, 16.46, 16.52, 16.60, 16.62, 16.64, 16.68

HW #5: 16.20, 16.28, 16.30, 16.32, 16.40, 16.44, 16.46, 16.52, 16.60, 16.62, 16.64, 16.68 hemistry 131 Lecture 10: Aldehydes and Ketones: Structure, Nomenclature, Physical Properties, and Reactivity hapter 16 in McMurry, Ballantine, et. al. 7 th edition W #5: 16.20, 16.28, 16.30, 16.32, 16.40,

More information

Review Experiments Formation of Polymers Reduction of Vanillin

Review Experiments Formation of Polymers Reduction of Vanillin Review Experiments Formation of Polymers What is a polymer? What is polymerization? What is the difference between an addition polymerization and a condensation polymerization? Which type of polymerization

More information

Chem 316/422 Beauchamp 1 Match the step number in the synthesis with the letter of the reagents listed just below.

Chem 316/422 Beauchamp 1 Match the step number in the synthesis with the letter of the reagents listed just below. hem 316/422 Beauchamp 1 Match the step number in the synthesis with the letter of the reagents listed just below. TP l Et step 8 4 5 eagents used in synthesis A B D E F a DMF (solvent) 1. (i-pr) 2 Li (LDA)/TF

More information

Dr. Mohamed El-Newehy

Dr. 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 information

Chapter 19 Substitutions at the Carbonyl Group

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

More information

CHEM 203. Final Exam December 18, 2013 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models

CHEM 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 information

Chapter 16. Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group. Physical Properties of Aldehydes and Ketones. Synthesis of Aldehydes

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

More information

Experiment : Reduction of Ethyl Acetoacetate

Experiment : Reduction of Ethyl Acetoacetate Experiment 7-2007: eduction of Ethyl Acetoacetate EXPEIMENT 7: eduction of Carbonyl Compounds: Achiral and Chiral eduction elevant sections in the text: Fox & Whitesell, 3 rd Ed. Chapter 12, pg.572-584.

More information

Reducing Agents. Linda M. Sweeting 1998

Reducing 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 information