Carbonyls (Ch ketones and aldehydes and carboxylic acids derivatives)

Size: px
Start display at page:

Download "Carbonyls (Ch ketones and aldehydes and carboxylic acids derivatives)"

Transcription

1 arbonyls (h ketones and aldehydes and carboxylic acids derivatives) +δ -δ ' - sp 2 - trigonal planar (120 0 ) - strongly polarized double bond eactivity? addition nucleophilic 1

2 Nucleophilic Addition Nu Nu ' ' - hange of hybridation - Adding complexity to the molecular structure - onverting a carbonyl to alcohol 2

3 Nucleophilic Addition-Elimination at Acyl arbon Aldehydes and ketones undergo nucleophilic additions to the carbonyl group ' ' + Nu Nu Tetrahedral intermediate Nu- ' -- + Nu - Nu A typical reaction of carboxylic acids and their derivatives is nucleophilic addition-elimination. The first step is nucleophilic addition to the carbonyl to give a tetrahedral intermediate, but the presence of a good leaving group (X) at this site results in an elimination that regenerates the trigonal carbonyl. X Nucleophilic addition + Nu - X - - Nu Elimination Nu + X - Tetrahedral intermediate This reaction mechanism is employed in many biological systems, and biochemists call them acyl transfer reactions.

4 - Example ydrolysis of an Acyl hloride --l Nucleophilic addition + - Nucleophile --l Tetrahedral intermediate --l + - Elimination -l This reaction proceeds well because of the great reactivity of the acyl chloride towards nucleophilic addition and the good leaving group ability of l - in the cleavage step.

5 Important Factors in the Addition-Elimination eaction eactivity of the Acyl arbon Electronic influences that increase the electropositive character of the acyl carbon enhance the rate of nucleophilic addition. Nu - δ+ δ --X Stability of the Leaving Group As the stability of X - increases, it becomes a better leaving group. As the electronegativity of X increases, the rate of nucleophilic addition increases. - --X Nu --Nu + X -

6 Acid atalysis Acid catalysis is important in both the addition and elimination steps. Protonation of the carbonyl --X + -Nu X + Nu - Provides electrophilic catalysis + - of addition --X + -Nu Protonation of leaving group - --X Nu + -Nu Deprotonation - --Nu X- Nu - --X Nu- + deprotonation Nu X Nu Tetrahedral intermediate Electrophilic catalysis of elimination Nu + Nu - --Nu + -Nu Acyl additionelimination product + -X + -Nu Protonated (better) leaving group

7 The Mechanism of Acid-atalyzed Esterification 6 5 AID Protonation Addition ESTE Deprotonation Elimination 6 5 proton transfer 3

8 Quiz Acid catalysis is important in nucleophilic addition-elimination at acyl carbon. Sketch the general mechanism for this reaction, indicating where the catalysis occurs. X + -Nu Nu + -X

9 Protonation of carbonyl group + - X + -Nu X + - X enhanced reactivity towards nucleophiles addition step - + Nu - X Nu tetrahedral intermediate + Nu - acid catalysis Protonation of leaving group - X + -Nu Nu cleavage step X- Nu Nu better leaving Nu - group X- Nu + -X Nu - + Nu + -Nu acid catalysis

10 Tutorial on arrow notation and mechanisms 10

11 Back to ketones and aldehydes now! 11

12 Mechanism of reduction - 3 B- ' ' ' ' ' Ease of reduction 12

13 arbon (formal) oxidation states () +3 -()

14 From the qualitative point of view xidation eduction Gaining (increase ox state) Loosing (decrease ox #) Loosing Gaining 2 3 reduction 2 () oxidation 14

15 Aldehyde alcohol 2 LiAl 4 NaB 4 r Mn - 4 s 4 e 4+ 15

16 -l ydride Transfer Mechanism Li + ( 3 ) - 3 -Al-( 3 ) 3 ( 3 ) 3 - is a nucleophile - -l A specific example l (1) LiAl(-t-Bu) 3, -78 o (2) 2 - -l + l - l - is a good leaving group Note selective reduction of acyl chloride in presence of nitro group. N 2 p-nitrobenzoyl chloride N 2 p-nitrobenzaldehyde

17 eduction of Esters with DIBAL- Esters are selectively reduced to aldehydes with DIBAL- when one equivalent of the reducing agent is used at low temperature. ' Ester (1) 1.0 eq (i-bu) 2 Al, -78 o (2) 2 Aldehyde A Proposed Mechanism DIBAL- is a trivalent aluminum species and is coordinatively unsaturated (i.e., a Lewis acid). The aluminum complexes with a nonbonding electron pair of the carbonyl oxygen i-bu Al - i-bu -' i-bu i-bu + - Al - -' A hydridoaluminate (Lewis complex)

18 ydride Transfer Nucleophilic Addition to the arbonyl i-bu i-bu + - Al - -' hydride transfer reduction -- -' Al(i-Bu) Al(i-Bu) Aldehyde At higher temperature and with excess reagent, the aldehyde products are reduced to primary alcohols.

19 5. Using rganometallic compounds (hemistry of carbanions) -δ +δ M M M M Na, K Mg, Li Pb, Sn, g, Tl explosive Versatile and useful strong base (-abstraction), strong nucleophiles 19

20 Preparation Br + 2 Li Li + LiBr Ethers are the preferred solvents but ethers are slowly attacked and decomposed 20

21 Grignard reagents the most popular Mg X -Mg-X - possible with a great variety of - ethers as solvent are crucial to the success of the reaction Mg X 2 Mg + MgX2 21

22 Grignard reagents the most popular Mg X -Mg-X - possible with a great variety of - ethers as solvent are crucial to the success of the reaction Mg X 2 Mg + MgX2 22

23 -d +d - M [M Mg, Li] The strong polarity of the M- bond and the consequent carbanionic character determines the reactivity 1) superstrong base MgX Mg X MgX --MgX ()- ()-MgX 23

24 Nucleophilic Addition (prep. of ) -MgX MgX ' ' ' Use acid hydrolysis to avoid precipitation of Mg() 2 24

25 Formation of alcohols -MgX Formaldehyde 1 0 -MgX Aldehyde 2 0 -MgX ketone 3 0 ' ' 25

26 eaction with both esters and acyl halides -MgX 3 0 ' -MgX Two identical groups 26

27 Planning a Grignard Synthesis We can synthesize ANY alcohol Et Et PhMgBr Et Et EtMgBr Ph 2 EtMgBr Et Ph Ph 27

28 estrictions Incompatible with any function that can be deprotonated -, -N 2, -N, - 2, -S 3, -S, --, aldehyde, ketone, esters, amide -N 2, -N, epoxide Grignard carbonatation to lenght the chain by one atom -MgX + esterification - 3 LiAl 4 28

29 29

30 30

31 31

32 First General Mechanism ' top δ+ Nu - δ- bottom sp 2 -hybridized carbon trigonal planar ' Nu - (and enantiomer) sp 3 -hybridized carbon tetrahedral E + ' -E Nu Addition product (racemic) sp 3 -hybridized carbon tetrahedral In these additions, E + is often a proton or metal ion.

33 Second General Mechanism ' δ+ δ- + -A acid catalyst Fast and reversible protonation eversible addition (and other enantiomer) ' + Nu Nu A Deprotonation ' + - Nu ' Addition product (racemic) ' + + A Protonated carbonyl (an oxonium cation) is more reactive towards nucleophilic addition + -A Acid catayst is regenerated -

34 elative eactivity Aldehydes versus Ketones Generally, aldehydes are more reactive than ketones because of both steric and electronic factors. Steric Factors When a nucleophile adds to the carbonyl group, the reaction center changes from trigonal planar (sp 2 ) to tetrahedral (sp 3 ) there is a closing of the angle between and '() groups from ~120 o to ~109 o. ()' ~120 o trigonal planar + Nu - ()' ~109 o tetrahedral With ketones, where and ' are alkyl or aryl groups, there is more buildup of steric strain as the groups move closer together than there is with aldehydes, where at least one of the groups being squeezed together is the very small hydrogen atom. - Nu

35 Electronic Factors A ketone carbonyl is stabilized relative to that of an aldehyde by the presence of two electron-releasing alkyl groups. δ δ Less stable, so More stable, more reactive δ+ δ+ so less reactive ' This diminishing of carbon charge in ketones contributes to their lower reactivity compared with that of aldehydes. Alkyl ketones are generally more reactive than aryl ketones because of greater electronic stabilization of the starting state of the latter by π- electron delocalization. δ + - etc. δ+ SUMMAY Any reduction in the partial positive charge on the carbon decreases its reactivity in nucleophilic addition. Any increase, e.g., by the presence of a strongly electron withdrawing group like -F 3, increases reactivity.

36 Addition eactions of Aldehydes and Ketones Addition of Water and Alcohols ydrates and Acetals ydrates gem-diols When aldehydes or ketones are dissolved in aqueous media, an equilibrium is established between the carbonyl compound and its hydrate. The hydrate is a geminal diol ("gem-diol"). ' + 2 K ' The position of equilibrium depends on the size and electronic effects of the groups. For most ketones, K' K[ 2 ] << 1. Most ketones exist essentially 100% in the carbonyl form. Aldehydes hydrate somewhat more extensively. Bulky and/or electron-donating groups stabilize the carbonyl compound in the above equilibrium. Electron-withdrawing groups destabilize the carbonyl compound and promote formation of the hydrate. These factors are illustrated in the table that follows.

37 Mechanism for ydrate Formation + - no acid catalysis water is the nucleophile rapid deprotonation and reprotonation yields the hydrate The rate of hydration is much faster under basic (higher p) or acidic (lower p) conditions than at p 7.

38 Additions of Alcohols emiacetals and Acetals Alcohols (-) add to carbonyl compounds like water does. ne important difference is that, overall, two molecules of can react with one of an aldehyde or ketone. A hemiacetal is formed from the addition of one molecule of. + ' ' emiacetal An acetal results from the addition of two molecules of. ' + 2 ' Acetal ' + 2 If the carbonyl compound is a ketone, the terms hemiketal and ketal are often but not always used in place of hemiacetal and acetal.

39 Typical eaction onditions for Acetal Formation The rate of the addition of alcohol is accelerated by acid and, like the hydration reaction, there is an equilibrium between the carbonyl compound and the tetrahedral product. To promote hemiacetal and acetal formation, the reaction is run by allowing the aldehyde to stand with a large excess of the alcohol with a small amount of anhydrous acid. The water produced can be removed as an azeotrope with benzene to drive the reaction to completion. A Mechanism for Acetal Formation Proton transfer ' ' ' ' emiacetal The hemiacetal usually cannot be isolated because of instability.

40 emiacetals Most acyclic hemiacetals are unstable and cannot be isolated. - ' But cyclic hemiacetals with 5- and 6-membered rings are stable and are widely found in carbohydrates (sugars and polysaccharides like cellulose and starch). Intramolecular hemiacetal formation proton + transfer 4-ydroxybutanal - yclic hemi-acetal stable

41 ydrolysis of Acetals All the steps in acetal formation are reversible. In an aqueous acid solution, acetals hydrolyze back to aldehydes. ' Acetal ' Aldehyde + 2 Mechanism ' - Acetal ' + - ' ' ' - emiacetal ' +

42 Quiz ircle the full acetal function in the compound below and provide the structures of the products from the hydrolysis reaction

43 Quiz For the reaction of ethanal and ethanol, (1) Draw the structure of the hemiacetal. (2) Draw the structure of the full acetal. 3 -Et Et 3 -Et (3) omplete this equation for the reaction of cyclopentanone with 1,2-ethanediol to produce a full acetal

44 Acetals as Protecting Groups While acetals readily hydrolyze back to the carbonyl compound in the presence of acid as a catalyst, they are stable to bases, even strong bases. ' + 2 ' '' '' - 2 no reaction Acetals often are used to protect aldehyde and ketone functions from undesired reactions in the presence of strong bases during syntheses. The acetal function, a geminal (1,1) diether, is not reactive towards nucleophiles, and its hydrogens are very non-acidic.

45 An Example The Selective eduction of an Ester in the Presence of a Ketone This is the desired conversion, but to selectively reduce the ester function it is necessary to protect (or mask) the ketone function. Use of protecting group Formation of cyclic ketal protective group ydrolysis removal of protecting group Ketal-ester 2 (1) LiAl 4, ether (2) 2 Ester reduction (ketone would, 2 if not protected, have been reduced, also)

46 Imines Addition of 1 o Amines '() Aldehyde or ketone + 2 N'' 1 o Amine 3 + N '' 2 + '() Imine, (E) & (Z) isomers Mechanism + N 2 '' + 2 N'' - N'' Amino alcohol N '' Imine 2 N + '' Iminium ion - 2 N'' 2 + Note All steps are reversible, so imines hydrolyze to carbonyl compounds in aqueous acid solution.

47 Imine formation proceeds fastest within a p range where there are optimal concentrations of the species involved in the nucleophilic addition step. This key step involves the free base attacking the more reactive protonated carbonyl compound. The concentrations of these two species depend on the p N [Key species] + 3 N- 2 N- + + p eaction ate Profile xn. rate The maximum reaction rate is found within a p range in which both key reactive species have reasonable concentrations p

48 3 Imine-Type arbonyl Derivatives + 2 N- hydroxylamine - 2 N- 3 an oxime + 2 N-N hydrazine N-N 2-2 a hydrazone N-N phenylhydrazine 2 N N-N- N 2 2,4-dinitrophenylhydrazine + 2 N-NN 2 semicarbazide - 2 N-N N - 2 N-NN a phenylhydrazone N-N- N 2 a 2,4-dinitrophenylhydrazone a semicarbazone

49 Addition of ydrogen yanide yanohydrins ydrogen cyanide (N) adds to aldehydes and unhindered ketones to produce cyanohydrins. + - N - N yanohydrins ' + - N - N (unhindered) ' In the reaction, a mineral acid is added to a mixture of the carbonyl compound and sodium cyanide. Too much acid slows the reaction by tying up the nucleophilic cyanide ion as N. The following sequence describes the mechanism of cyanohydrin formation. ' - + N slow yanide ion (a good nucleophile) - - N ' - N - N ' + - N

50 Synthetic Uses of yanohydrins (1) ydrolysis of the nitrile function gives α-hydroxyacids or α,β-unsaturated acids. N l 2, heat 95% 2 S 4 heat, Methyl-2-butenoic acid (2) eduction with lithium aluminum hydride gives β-aminoalcohols. - 2-ydroxy-2-methylbutanoic acid N N LiAl 4 N 2 1-Aminomethylcyclohexanol

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

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

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

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

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

Chem 263 Nov 14, e.g.: Fill the reagents to finish the reactions (only inorganic reagents)

Chem 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 information

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

Lecture 15. More Carbonyl Chemistry. Alcohols React with Aldehydes and Ketones in two steps first O R'OH, H + OR 2ROH 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 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

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

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

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

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 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 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

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

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

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

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 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

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

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

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 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

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

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

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

Carbonyl Compounds. Introduction

Carbonyl 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 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

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

Chapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Chapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group Chapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al

More information

21.1 Introduction Carboxylic Acids Nomenclature of Carboxylic Acids. Acids Structure and Properties of Carboxylic Acids.

21.1 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 information

ζ ε δ γ β α α β γ δ ε ζ

ζ ε δ γ β α α β γ δ ε ζ hem 263 Nov 17, 2016 eactions at the α-arbon The alpha carbon is the carbon adjacent to the carbonyl carbon. Beta is the next one, followed by gamma, delta, epsilon, and so on. 2 ε 2 δ 2 γ 2 2 β α The

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

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

Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group

Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al

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

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

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

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

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

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

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

Aldehydes and Ketones: Nucleophilic Addition Reactions

Aldehydes 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 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

Topic 4 Aldehydes and Ketones

Topic 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 information

TABLE 18-1 Some Common Classes of Carbonyl Compounds

TABLE 18-1 Some Common Classes of Carbonyl Compounds TABLE 18-1 Some ommon lasses of arbonyl ompounds lass General Formula lass General Formula ' 99 ' 99 ketones aldehydes carboxylic acids acid chlorides ' esters 999 amides ' 99 ' 99l ' 99N 2 Figure Number:

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 Nitriles

Carboxylic Acids and Nitriles Carboxylic Acids and Nitriles Why this Chapter? Carboxylic acids present in many industrial processes and most biological processes They are the starting materials from which other acyl derivatives are

More information

Aldehydes & Ketones I

Aldehydes & 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 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

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

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 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

Alpha Substitution and Condensations of Enols and Enolate Ions. Alpha Substitution

Alpha Substitution and Condensations of Enols and Enolate Ions. Alpha Substitution Alpha Substitution and ondensations of Enols and Enolate Ions hap 23 W: 27, 28, 30, 31, 37, 39, 42-44, 47, 51, 54-56 Alpha Substitution Replacement of a hydrogen on the carbon adjacent to the carbonyl,

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

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

Chapter 20 Carboxylic Acid Derivatives Nucleophilic Acyl Substitution

Chapter 20 Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Chapter 20 Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Nomenclature: In carboxylic acid chlorides, anhydrides, esters and amides, the parent is the carboxylic acid. In each case be sure

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

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

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

O O O CH 2 O 7. 2 = C=O hydration H B. 6 = reverse aldol H O. 9b = acetal formation add alcohol (step 2)

O O O CH 2 O 7. 2 = C=O hydration H B. 6 = reverse aldol H O. 9b = acetal formation add alcohol (step 2) 1 equences For Practice 1. 1 2 3 7 2 6 5 4 8 9 Possible Key 3 = AD + oxidation 1 2 3 4 5 3 2 1 AD + 7 1 = AD + oxidation 7 = aldol AD 2 = = hydration 2 6 6 = aldol AD + AD 5 5 = β-keto decarboxylation

More information

Aldehydes and Ketones 2. Based on Organic Chemistry, J. G. Smith 3rde.

Aldehydes and Ketones 2. Based on Organic Chemistry, J. G. Smith 3rde. Aldehydes and Ketones 2 Based on Organic Chemistry, J. G. Smith 3rde. The Wittig Reaction Wittig reaction, named for German chemist Georg Wittig, who was awarded the Nobel Prize in Chemistry in 1979 for

More information

Chapter 20: Carboxylic Acids

Chapter 20: Carboxylic Acids 1 Chapter 20: Carboxylic Acids I. Introduction: Carboxylic acid structure: Classification of carboxylic acids: A carboxylic acid donates protons by the heterocyclic cleavage of the O-H bond, generating

More information

CHM 292 Final Exam Answer Key

CHM 292 Final Exam Answer Key CHM 292 Final Exam Answer Key 1. Predict the product(s) of the following reactions (5 points each; 35 points total). May 7, 2013 Acid catalyzed elimination to form the most highly substituted alkene possible

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

Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions

Chapter 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 information

Chapter 22: Amines. Organic derivatives of ammonia, NH 3. Nitrogen atom have a lone pair of electrons, making the amine both basic and nucleophilic

Chapter 22: Amines. Organic derivatives of ammonia, NH 3. Nitrogen atom have a lone pair of electrons, making the amine both basic and nucleophilic hapter 22: Amines. rganic derivatives of ammonia, 3. itrogen atom have a lone pair of electrons, making the amine both basic and nucleophilic 22.1: Amines omenclature. (please read) sp 3 Amines are classified

More information

Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions

Chapter 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 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

CH 19: Aldehydes and Ketones

CH 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 information

Section Practice Exam II Solutions

Section Practice Exam II Solutions Paul Bracher Chem 30 Section 7 Section Practice Exam II s Whether problems old r problems new, You d better practice, r you ll fail exam II. -- Anonymous TF Problem 1 a) Rank the following series of electrophiles

More information

Chapter 19 Carboxylic Acids

Chapter 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 information

Background Information

Background Information ackground nformation ntroduction to Condensation eactions Condensation reactions occur between the α-carbon of one carbonyl-containing functional group and the carbonyl carbon of a second carbonyl-containing

More information

(Neither an oxidation or reduction: Addition or loss of H +, H 2 O, HX).

(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 information

Lecture Notes Chemistry Mukund P. Sibi Lecture 36 Synthesis of Amines

Lecture Notes Chemistry Mukund P. Sibi Lecture 36 Synthesis of Amines Lecture otes hemistry 42-2008 Mukund P. Sibi Synthesis of Amines Amines can be prepared from a variety of starting materials. All of these methods involve functional group transformations. The main methods

More information

Amines Reading Study Problems Key Concepts and Skills Lecture Topics: Amines: structure and nomenclature

Amines 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 information

THE CHEMISTRY OF THE CARBONYL GROUP

THE CHEMISTRY OF THE CARBONYL GROUP TE CEMISTY F TE CABYL GUP Professor Tim Donohoe 8 lectures, T, weeks 1-4, 2007 andout A C C You will be able to download copies of the handouts from this course at http://users.ox.ac.uk/~magd1571/teaching/teaching.htm

More information

Topic 6 Alkyl halide and carbonyl compounds Organic compounds containing a halogen

Topic 6 Alkyl halide and carbonyl compounds Organic compounds containing a halogen Topic 6 Alkyl halide and carbonyl compounds rganic compounds containing a halogen ompounds are named in standard way 3 1 3 3 2 3 2-iodo-2-methylpropane (tertiary alkyl halide) l 3 4-chlorotoluene (aryl

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

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

Exam 1 (Monday, July 6, 2015)

Exam 1 (Monday, July 6, 2015) Chem 231 Summer 2015 Assigned Homework Problems Last updated: Friday, July 24, 2015 Problems Assigned from Essential Organic Chemistry, 2 nd Edition, Paula Yurkanis Bruice, Prentice Hall, New York, NY,

More information

Chapter 17. Reactions of Aromatic Compounds

Chapter 17. Reactions of Aromatic Compounds Chapter 17 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Although benzene s pi electrons are in a stable aromatic system, they are available to attack a strong electrophile to give

More information

CHEM 234: Organic Chemistry II Reaction Sheets

CHEM 234: Organic Chemistry II Reaction Sheets EM234:rganichemistry eactionsheets ucleophilic addition at carbonyl groups: Grignards and reducing agents u: u u u: u u = or = or l u u u ucleophilic addition at carbonyl groups: oxygen and nitrogen nucleophiles:

More information

Topic 6 Alkyl halide and carbonyl compounds Organic compounds containing a halogen

Topic 6 Alkyl halide and carbonyl compounds Organic compounds containing a halogen Topic 6 Alkyl halide and carbonyl compounds rganic compounds containing a halogen ompounds are named in standard way, eg: 3 1 3 3 2 3 2-iodo-2-methylpropane (tertiary alkyl halide) l 3 4-chlorotoluene

More information

Chapter 19. Carbonyl Compounds III Reaction at the α-carbon

Chapter 19. Carbonyl Compounds III Reaction at the α-carbon Chapter 19. Carbonyl Compounds III Reaction at the α-carbon There is a basic hydrogen (α hydrogen) on α carbon, which can be removed by a strong base. 19.1 The Acidity of α-hydrogens A hydrogen bonded

More information

Chem 263 Nov 28, Reactions of Carboxylic Acids and Derivatives: Strong Nucleophiles

Chem 263 Nov 28, Reactions of Carboxylic Acids and Derivatives: Strong Nucleophiles Chem 263 ov 28, 2013 eactions of Carboxylic Acids and Derivatives: Strong ucleophiles The strong nucleophiles (u: - ) that we have learned in this course are either hydride anion ( - ) or alkyl anion (

More information

Ch 20 Carboxylic Acids and Nitriles

Ch 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 information

Electrophile = electron loving = any general electron pair acceptor = Lewis acid, (often an acidic proton)

Electrophile = electron loving = any general electron pair acceptor = Lewis acid, (often an acidic proton) 314 Arrow Pushing practice/eauchamp 1 Electrophile = electron loving = any general electron pair acceptor = Lewis acid, (often an acidic proton) ucleophile = nucleus/positive loving = any general electron

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

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

Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions. McMurray Text Chapter 21

Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions. McMurray Text Chapter 21 Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution eactions McMurray Text Chapter 21 Carboxylic Acid Derivatives X Acid alide Ester ' Acid Anhydride ' N 2 Amide (1 ) Nomenclature Acid alides

More information

Module 4 revision guide: Compounds with C=O group

Module 4 revision guide: Compounds with C=O group opyright N Goalby Bancroft's School Module 4 revision guide: ompounds with = group arbonyls: Aldehydes and Ketones arbonyls are compounds with a = bond, they can be either aldehydes or ketones. 3 ethanal

More information

Name/CG: 2012 Term 2 Organic Chemistry Revision (Session II) Deductive Question

Name/CG: 2012 Term 2 Organic Chemistry Revision (Session II) Deductive Question Name/G: 2012 Term 2 rganic hemistry Revision (Session II) Deductive Question 1(a) A yellow liquid A, 7 7 N 2, reacts with alkaline potassium manganate (VII) and on acidification gives a yellow solid B,

More information

Brønsted Acid Proton donor Base Proton acceptor O CH 3 COH + H H 3 O + + CH 3 CO -

Brønsted Acid Proton donor Base Proton acceptor O CH 3 COH + H H 3 O + + CH 3 CO - hap 7. Acid and Bases Brønsted Acid Proton donor Base Proton acceptor 3 3 3-2 acid base conj. acid conj. base 3 2 S 4 3 - S 4 base acid conj. acid conj. base 6 5 N 2 N 2 6 5 N - N 3 acid base conj. base

More information

Aldehydes and Ketones : Aldol Reactions

Aldehydes and Ketones : Aldol Reactions Aldehydes and Ketones : Aldol Reactions The Acidity of the a Hydrogens of Carbonyl Compounds: Enolate Anions Hydrogens on carbons a to carbonyls are unusually acidic The resulting anion is stabilized by

More information

Module9. Nuclear Magnetic Resonance Spectroscopy Nuclear Magnetic Resonance (NMR) spectroscopy - Chemical shift - Integration of signal area

Module9. Nuclear Magnetic Resonance Spectroscopy Nuclear Magnetic Resonance (NMR) spectroscopy - Chemical shift - Integration of signal area 1 CHEMISTRY 263 HOME WORK Lecture Topics: Module7. Hydrogenation of Alkenes The Function of the Catalyst - Syn and anti- addition Hydrogenation of Alkynes - Syn- addition of hydrogen: Synthesis of cis-alkenes

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 19: Amines. Introduction

Chapter 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 information

1/4/2011. Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds

1/4/2011. Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds Chapter 18 Aldehydes and Ketones Reaction at the -carbon of carbonyl compounds The Acidity of the Hydrogens of Carbonyl Compounds: Enolate Anions Hydrogens on carbons to carbonyls are unusually acidic

More information

H H O C C O H Carboxylic Acids and Derivatives C CH 2 C. N Goalby chemrevise.org. Strength of carboxylic acids.

H H O C C O H Carboxylic Acids and Derivatives C CH 2 C. N Goalby chemrevise.org. Strength of carboxylic acids. 19 arboxylic Acids and Derivatives Naming arboxylic acids These have the ending -oic acid but no number is necessary for the acid group as it must always be at the end of the chain. The numbering always

More information