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CHE-302 Review.

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1 CHE-302 Review

2 Nomenclature Syntheses Reactions Mechanisms Spectroscopy

3 Aromatic Hydrocarbons (Electrophilic Aromatic Substitution)
Spectroscopy (infrared & H-nmr) Arenes Aldehydes & Ketones Carboxylic Acids Functional Derivatives of Carboxylic Acids Acid Chlorides, Anhydrides, Amides, Esters Carbanions Amines & Diazonium Salts Phenols

4 Mechanisms: Electrophilic Aromatic Substitution Nitration Sulfonation Halogenation Friedel-Crafts Alkylation & Acylation Nucleophilic Addition to Carbonyl Nucleophilic Addition to Carbonyl, Acid Catalyzed Nucleophilic Acyl Substitution Nucleophilic Acyl Substitution, Acid Catalyzed

5 Aromatic Hydrocarbons
aliphatic aromatic alkanes alkenes alkynes

6 Aliphatic compounds: open-chain compounds and ring compounds that are chemically similar to open-chain compounds. Alkanes, alkenes, alkynes, dienes, alicyclics, etc. Aromatic compounds: unsaturated ring compounds that are far more stable than they should be and resist the addition reactions typical of unsaturated aliphatic compounds. Benzene and related compounds.

7 Nomenclature for benzene:
monosubstituted benzenes: Special names:

8

9 Electrophilic Aromatic Substitution (Aromatic compounds)
Ar-H = aromatic compound 1. Nitration Ar-H HNO3, H2SO4  Ar-NO H2O Sulfonation Ar-H H2SO4, SO3  Ar-SO3H H2O Halogenation Ar-H X2, Fe  Ar-X HX Friedel-Crafts alkylation Ar-H R-X, AlCl3  Ar-R HX

10 Friedel-Crafts alkylation (variations)
Ar-H R-X, AlCl3  Ar-R HX Ar-H R-OH, H+  Ar-R H2O c) Ar-H Alkene, H+  Ar-R

11 Common substituent groups and their effect on EAS:
-NH2, -NHR, -NR2 -OH -OR -NHCOCH3 -C6H5 -R -H -X -CHO, -COR -SO3H -COOH, -COOR -CN -NR3+ -NO2 ortho/para directors increasing reactivity meta directors

12 If there is more than one group on the benzene ring:
The group that is more activating (higher on “the list”) will direct the next substitution. You will get little or no substitution between groups that are meta- to each other.

13 “Generic” Electrophilic Aromatic Substitution mechanism:

14 Mechanism for nitration:

15 Mechanism for sulfonation:

16 Mechanism for halogenation:

17 Mechanism for Friedel-Crafts alkylation:

18 Mechanism for Friedel-Crafts with an alcohol & acid

19 Mechanism for Friedel-Crafts with alkene & acid:
electrophile in Friedel-Crafts alkylation = carbocation

20 Arenes alkylbenzenes alkenylbenzenes alkynylbenzenes etc.

21 Alkylbenzenes, nomenclature:
Special names

22 others named as “alkylbenzenes”:

23 Use of phenyl C6H5- = “phenyl”
do not confuse phenyl (C6H5-) with benzyl (C6H5CH2-)

24 Alkenylbenzenes, nomenclature:

25 Alkylbenzenes, syntheses:
Friedel-Crafts alkylation Modification of a side chain: a) addition of hydrogen to an alkene b) reduction of an alkylhalide i) hydrolysis of Grignard reagent ii) active metal and acid c) Corey-House synthesis

26 Alkynylbenzenes, nomenclature:

27 Friedel-Crafts alkylation

28 Friedel-Crafts limitations:
Polyalkylation Possible rearrangement R-X cannot be Ar-X NR when the benzene ring is less reactive than bromobenzene NR with -NH2, -NHR, -NR2 groups

29 Modification of side chain:

30 Alkylbenzenes, reactions:
Reduction Oxidation EAS a) nitration b) sulfonation c) halogenation d) Friedel-Crafts alkylation Side chain free radical halogenation

31

32 Alkylbenzenes, EAS -R is electron releasing. Activates to EAS and directs ortho/para

33 Alkylbenzenes, free radical halogenation in side chain:
Benzyl free radical

34 Alkenylbenzenes, syntheses:
Modification of side chain: a) dehydrohalogenation of alkyl halide b) dehydration of alcohol c) dehalogenation of vicinal dihalide d) reduction of alkyne (2. Friedel-Crafts alkylation)

35 Alkenylbenzenes, synthesis modification of side chain

36 Alkenylbenzenes, reactions:
Reduction Oxidation EAS Side chain a) add’n of H2 j) oxymercuration b) add’n of X2 k) hydroboration c) add’n of HX l) addition of free rad. d) add’n of H2SO4 m) add’n of carbenes e) add’n of H2O n) epoxidation f) add’n of X2 & H2O o) hydroxylation g) dimerization p) allylic halogenation h) alkylation q) ozonolysis i) dimerization r) vigorous oxidation

37 Alkenylbenzenes, reactions: reduction

38 Alkenylbenzenes, reactions oxidation

39 Alkenylbenzenes, reactions EAS?

40

41

42 100 syn-oxidation; make a model!

43 Alkynylbenzenes, syntheses:
Dehydrohalogenation of vicinal dihalides

44 Alkynylbenzenes, reactions:
Reduction Oxidation EAS Side chain a) reduction e) as acids b) add’n of X2 f) with Ag+ c) add’n of HX g) oxidation d) add’n of H2O, H+

45 Alkynylbenzenes, reactions: reduction
Anti- Syn-

46 Alkynylbenzenes, reactions: oxidation

47 Alkynylbenzenes, reactions EAS?

48 Alkynylbenzenes, reactions: side chain:

49

50 Aldehydes and Ketones

51 Nomenclature: Aldehydes, common names: Derived from the common names of carboxylic acids; drop –ic acid suffix and add –aldehyde. CH3 CH3CH2CH2CH=O CH3CHCH=O butyraldehyde isobutyraldehyde (α-methylpropionaldehyde)

52 Aldehydes, IUPAC nomenclature:
Parent chain = longest continuous carbon chain containing the carbonyl group; alkane, drop –e, add –al. (note: no locant, -CH=O is carbon #1.) CH3 CH3CH2CH2CH=O CH3CHCH=O butanal methylpropanal H2C=O CH3CH=O methanal ethanal

53 Ketones, common names: Special name: acetone “alkyl alkyl ketone” or “dialkyl ketone”

54 (o)phenones: Derived from common name of carboxylic acid, drop –ic acid, add –(o)phenone.

55 Ketones: IUPAC nomenclature:
Parent = longest continuous carbon chain containing the carbonyl group. Alkane, drop –e, add –one. Prefix a locant for the position of the carbonyl using the principle of lower number.

56 Aldehydes, syntheses: Oxidation of 1o alcohols Oxidation of methylaromatics Reduction of acid chlorides Ketones, syntheses: Oxidation of 2o alcohols Friedel-Crafts acylation Coupling of R2CuLi with acid chloride

57 Aldehydes synthesis 1) oxidation of primary alcohols:
RCH2-OH K2Cr2O7, special conditions  RCH=O RCH2-OH C5H5NHCrO3Cl  RCH=O (pyridinium chlorochromate) [With other oxidizing agents, primary alcohols  RCOOH]

58 Aldehyde synthesis: 2) oxidation of methylaromatics:
Aromatic aldehydes only!

59 Aldehyde synthesis: 3) reduction of acid chloride

60 Ketone synthesis: 1) oxidation of secondary alcohols

61 Ketone synthesis: 2) Friedel-Crafts acylation
Aromatic ketones (phenones) only!

62 Ketone synthesis: 3) coupling of RCOCl and R2CuLi

63 Aldehydes & ketones, reactions:
Oxidation Reduction Addition of cyanide Addition of derivatives of ammonia Addition of alcohols Cannizzaro reaction Addition of Grignard reagents 8) (Alpha-halogenation of ketones) 9) (Addition of carbanions)

64 nucleophilic addition to carbonyl:

65 Mechanism: nucleophilic addition to carbonyl
1) 2)

66 Mechanism: nucleophilic addition to carbonyl, acid catalyzed
1) 2) 3)

67 1) Oxidation Aldehydes (very easily oxidized!) CH3CH2CH2CH=O KMnO4, etc.  CH3CH2CH2COOH carboxylic acid CH3CH2CH2CH=O Ag+  CH3CH2CH2COO Ag Tollen’s test for easily oxidized compounds like aldehydes. (AgNO3, NH4OH(aq)) Silver mirror

68 b) Methyl ketones: Yellow ppt test for methyl ketones

69 2) Reduction: To alcohols

70

71 Reduction b) To hydrocarbons

72 3) Addition of cyanide

73 4) Addition of derivatives of ammonia

74

75 5) Addition of alcohols

76

77 Cannizzaro reaction. (self oxidation/reduction)
a reaction of aldehydes without α-hydrogens

78 Formaldehyde is the most easily oxidized aldehyde
Formaldehyde is the most easily oxidized aldehyde. When mixed with another aldehyde that doesn’t have any alpha-hydrogens and conc. NaOH, all of the formaldehyde is oxidized and all of the other aldehyde is reduced. Crossed Cannizzaro:

79 7) Addition of Grignard reagents.

80 Planning a Grignard synthesis of an alcohol:
The alcohol carbon comes from the carbonyl compound. The new carbon-carbon bond is to the alcohol carbon. New carbon-carbon bond

81 HX Mg ROH RX RMgX larger alcohol H2O ox. R´OH -C=O

82 CH3 HBr CH3 Mg CH3 4-methyl-2-pentanol
CH3CHCH2OH CH3CHCH2Br CH3CHCH2MgBr H+ K2Cr2O CH3 CH3CH2OH CH3CH=O CH3CHCH2CHCH3 special cond OH 4-methyl-2-pentanol

83 Carboxylic Acids

84 Carboxylic acids, syntheses:
oxidation of primary alcohols RCH2OH K2Cr2O7  RCOOH 2. oxidation of arenes ArR KMnO4, heat  ArCOOH 3. carbonation of Grignard reagents RMgX CO2  RCO2MgX H+  RCOOH 4. hydrolysis of nitriles RCN H2O, H+, heat  RCOOH

85 oxidation of 1o alcohols:
CH3CH2CH2CH2-OH CrO3  CH3CH2CH2CO2H n-butyl alcohol butyric acid 1-butanol butanoic acid CH CH3 CH3CHCH2-OH KMnO4  CH3CHCOOH isobutyl alcohol isobutyric acid 2-methyl-1-propanol` methylpropanoic acid

86 oxidation of arenes: note: aromatic acids only!

87 carbonation of Grignard reagent:
R-X RMgX RCO2MgX RCOOH Increases the carbon chain by one carbon. Mg CO2 H+ CH3CH2CH2-Br CH3CH2CH2MgBr CH3CH2CH2COOH n-propyl bromide butyric acid Mg CO H+

88 Hydrolysis of a nitrile:
H2O, H+ R-CN R-CO2H heat H2O, OH- R-CN R-CO H+  R-CO2H R-X NaCN  R-CN H+, H2O, heat  RCOOH 1o alkyl halide Adds one more carbon to the chain. R-X must be 1o or CH3!

89 carboxylic acids, reactions:
as acids conversion into functional derivatives a)  acid chlorides b)  esters c)  amides reduction alpha-halogenation EAS

90 as acids: with active metals RCO2H Na  RCO2-Na H2(g) with bases RCO2H NaOH  RCO2-Na H2O relative acid strength? CH4 < NH3 < HCCH < ROH < HOH < H2CO3 < RCO2H < HF quantitative HA H2O  H3O A ionization in water Ka = [H3O+] [A-] / [HA]

91 Conversion into functional derivatives:
 acid chlorides

92  esters “direct” esterification: RCOOH R´OH  RCO2R´ H2O -reversible and often does not favor the ester -use an excess of the alcohol or acid to shift equilibrium -or remove the products to shift equilibrium to completion “indirect” esterification: RCOOH PCl3  RCOCl R´OH  RCO2R´ -convert the acid into the acid chloride first; not reversible

93  amides “indirect” only! RCOOH SOCl2  RCOCl NH3  RCONH2 amide Directly reacting ammonia with a carboxylic acid results in an ammonium salt: RCOOH NH3  RCOO-NH4+ acid base

94 Reduction: RCO2H LiAlH4; then H+  RCH2OH 1o alcohol Carboxylic acids resist catalytic reduction under normal conditions. RCOOH H2, Ni  NR

95 Alpha-halogenation: (Hell-Volhard-Zelinsky reaction)
RCH2COOH X2, P  RCHCOOH HX X α-haloacid X2 = Cl2, Br2

96 5. EAS: (-COOH is deactivating and meta- directing)

97 Functional Derivatives of Carboxylic Acids

98 Nomenclature: the functional derivatives’ names are derived from the common or IUPAC names of the corresponding carboxylic acids. Acid chlorides: change –ic acid to –yl chloride Anhydrides: change acid to anhydride

99 Amides: change –ic acid (common name) to –amide
-oic acid (IUPAC) to –amide Esters: change –ic acid to –ate preceded by the name of the alcohol group

100 Mechanism: Nucleophilic Acyl Substitution
1) 2)

101 Mechanism: nucleophilic acyl substitution, acid catalyzed
1) 2) 3)

102 Acid Chlorides Syntheses: SOCl2 RCOOH PCl  RCOCl PCl5

103 Acid chlorides, reactions:
Conversion into acids and derivatives: a) hydrolysis b) ammonolysis c) alcoholysis Friedel-Crafts acylation Coupling with lithium dialkylcopper Reduction

104 acid chlorides: conversion into acids and other derivatives

105 acid chlorides: Friedel-Crafts acylation

106 acid chlorides: coupling with lithium dialkylcopper

107 acid chlorides: reduction to aldehydes

108 Anhydrides, syntheses:
Buy the ones you want! Anhydrides, reactions: Conversion into carboxylic acids and derivatives. a) hydrolysis b) ammonolysis c) alcoholysis 2) Friedel-Crafts acylation

109

110 2) anhydrides, Friedel-Crafts acylation.

111 Amides, synthesis: Indirectly via acid chlorides.

112 Amides, reactions. 1) Hydrolysis.

113 Esters, syntheses: From acids RCO2H R’OH, H RCO2R’ H2O From acid chlorides and anhydrides RCOCl R’OH RCO2R’ HCl From esters (transesterification) RCO2R’ R”OH, H RCO2R” R’OH RCO2R’ R”ONa RCO2R” R’ONa

114 “Direct” esterification is reversible and requires use of LeChatelier’s principle to shift the equilibrium towards the products. “Indirect” is non-reversible.

115 In transesterification, an ester is made from another ester by exchanging the alcohol function.

116 Esters, reactions: Conversion into acids and derivatives a) hydrolysis b) ammonolysis c) alcoholysis Reaction with Grignard reagents Reduction a) catalytic b) chemical 4) Claisen condensation

117

118 Esters, reaction with Grignard reagents

119

120 Esters, reduction catalytic chemical

121

122 Carbanions | — C: – The conjugate bases of weak acids, strong bases, excellent nucleophiles.

123 1. Alpha-halogenation of ketones

124 Carbanions. The conjugate bases of weak acids; strong bases, good nucleophiles.
1. enolate anions 2. organometallic compounds 3. ylides 4. cyanide 5. acetylides

125 Aldehydes and ketones: nucleophilic addition
Esters and acid chlorides: nucleophilic acyl substitution Alkyl halides: SN2 Carbanions as the nucleophiles in the above reactions.

126 Carbanions as the nucleophiles in nucleophilic addition to aldehydes and ketones:
a) aldol condensation “crossed” aldol condensation b) aldol related reactions (see problem on page 811) c) addition of Grignard reagents d) Wittig reaction

127 a) Aldol condensation. The reaction of an aldehyde or ketone with dilute base or acid to form a beta-hydroxycarbonyl product.

128 nucleophilic addition by enolate ion.

129 Crossed aldol condensation:
If you react two aldehydes or ketones together in an aldol condensation, you will get four products. However, if one of the reactants doesn’t have any alpha hydrogens it can be condensed with another compound that does have alpha hydrogens to give only one organic product in a “crossed” aldol. NaOH

130 N.B. If the product of the aldol condensation under basic conditions is a “benzyl” alcohol, then it will spontaneously dehydrate to the α,β-unsaturated carbonyl.

131 Wittig reaction (synthesis of alkenes)
1975 Nobel Prize in Chemistry to Georg Wittig Ph = phenyl

132 Carbanions as the nucleophiles in nucleophilic acyl substitution of esters and acid chlorides.
a) Claisen condensation a reaction of esters that have alpha-hydrogens in basic solution to condense into beta-keto esters

133 Mechanism for the Claisen condensation:

134 Crossed Claisen condensation:

135 Carbanions II Carbanions as nucleophiles in SN2 reactions with alkyl halides. a) Malonate synthesis of carboxylic acids b) Acetoacetate synthesis of ketones c) 2-oxazoline synthesis of esters/carboxylic acids d) Organoborane synthesis of acids/ketones e) Enamine synthesis of aldehydes/ketones

136

137

138 Amines (organic ammonia) :NH3 :NH2R or RNH2 1o amine (R may be Ar)
:NR3 or R3N 3o amine NR4+ 4o ammonium salt

139 NB amines are classified by the class of the nitrogen, primary amines have one carbon bonded to N, secondary amines have two carbons attached directly to the N, etc. Nomenclature. Common aliphatic amines are named as “alkylamines”

140

141 Amines, syntheses: Reduction of nitro compounds 1o Ar Ar-NO H2,Ni  Ar-NH2 Ammonolysis of 1o or methyl halides R-X = 1o,CH3 R-X + NH3  R-NH2 Reductive amination avoids E2 R2C=O NH3, H2, Ni  R2CHNH2 Reduction of nitriles carbon R-CN H2, Ni  RCH2NH2 Hofmann degradation of amides - 1 carbon RCONH KOBr  RNH2

142 1. Reduction of nitro compounds:

143 Ammonolysis of 1o or methyl halides.

144 3. Reductive amination: Avoids E2

145 Reduction of nitriles R-CN H2, catalyst  R-CH2NH2 1o amine R-X NaCN  R-CN  RCH2NH2 primary amine with one additional carbon (R must be 1o or methyl)

146 5. Hofmann degradation of amides

147 Amine, reactions: As bases Alkylation Reductive amination Conversion into amides EAS Hofmann elimination from quarternary ammonium salts Reactions with nitrous acid

148 As bases a) with acids b) relative base strength c) Kb d) effect of groups on base strength

149 2. Alkylation (ammonolysis of alkyl halides)

150 3. Reductive amination

151 Conversion into amides
R-NH RCOCl  RCONHR HCl 1o N-subst. amide R2NH RCOCl  RCONR HCl 2o N,N-disubst. amide R3N RCOCl  NR 3o

152 EAS -NH2, -NHR, -NR2 are powerful activating groups and ortho/para directors a) nitration b) sulfonation c) halogenation d) Friedel-Crafts alkylation e) Friedel-Crafts acylation f) coupling with diazonium salts g) nitrosation

153 a) nitration

154 b) sulfonation

155 c) halogenation

156 Friedel-Crafts alkylation
NR with –NH2, -NHR, -NR2

157 Friedel-Crafts acylation
NR with –NH2, -NHR, -NR2

158 g) nitrosation

159 h) coupling with diazonium salts  azo dyes

160 Hofmann elimination from quarternary hydroxides
step 1, exhaustive methylation  4o salt step 2, reaction with Ag2O  4o hydroxide + AgX step 3, heat to eliminate  alkene(s) + R3N

161 7. Reactions with nitrous acid

162 Diazonium salts synthesis benzenediazonium ion

163 Diazonium salts, reactions
Coupling to form azo dyes Replacements a) -Br, -Cl, -CN b) -I c) -F d) -OH e) -H f) etc.

164 coupling to form azo dyes

165

166 Phenols Ar-OH Phenols are compounds with an –OH group attached to an aromatic carbon. Although they share the same functional group with alcohols, where the –OH group is attached to an aliphatic carbon, the chemistry of phenols is very different from that of alcohols.

167 Nomenclature. Phenols are usually named as substituted phenols. The methylphenols are given the special name, cresols. Some other phenols are named as hydroxy compounds.

168 phenols, syntheses: From diazonium salts 2. Alkali fusion of sulfonates

169 phenols, reactions: as acids ester formation ether formation EAS a) nitration f) nitrosation b) sulfonation g) coupling with diaz. salts c) halogenation h) Kolbe d) Friedel-Crafts alkylation i) Reimer-Tiemann e) Friedel-Crafts acylation

170 as acids: with active metals: with bases:
CH4 < NH3 < HCCH < ROH < H2O < phenols < H2CO3 < RCOOH < HF

171 ester formation (similar to alcohols)

172 ether formation (Williamson Synthesis)
Ar-O-Na R-X  Ar-O-R NaX note: R-X must be 1o or CH3 Because phenols are more acidic than water, it is possible to generate the phenoxide in situ using NaOH.

173 Electrophilic Aromatic Substitution
The –OH group is a powerful activating group in EAS and an ortho/para director. a) nitration

174 b) halogenation

175 c) sulfonation At low temperature the reaction is non-reversible and the lower Eact ortho-product is formed (rate control). At high temperature the reaction is reversible and the more stable para-product is formed (kinetic control).

176 d) Friedel-Crafts alkylation.

177 e) Friedel-Crafts acylation

178 Fries rearrangement of phenolic esters.

179 f) nitrosation

180 g) coupling with diazonium salts
(EAS with the weak electrophile diazonium)

181 h) Kolbe reaction (carbonation)

182 i) Reimer-Tiemann reaction

183 Nomenclature Syntheses Reactions Mechanisms Spectroscopy

184 Aromatic Hydrocarbons (Electrophilic Aromatic Substitution)
Spectroscopy (infrared & H-nmr) Arenes Aldehydes & Ketones Carboxylic Acids Functional Derivatives of Carboxylic Acids Acid Chlorides, Anhydrides, Amides, Esters Carbanions Amines & Diazonium Salts Phenols

185 Mechanisms: Electrophilic Aromatic Substitution Nitration Sulfonation Halogenation Friedel-Crafts Alkylation & Acylation Nucleophilic Addition to Carbonyl Nucleophilic Addition to Carbonyl, Acid Catalyzed Nucleophilic Acyl Substitution Nucleophilic Acyl Substitution, Acid Catalyzed

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