chapter18
TRANSCRIPT
18-18-11
Organic Organic ChemistryChemistry
William H. BrownWilliam H. Brown
Christopher S. FooteChristopher S. Foote
Brent L. IversonBrent L. Iverson
William H. BrownWilliam H. Brown
Christopher S. FooteChristopher S. Foote
Brent L. IversonBrent L. Iverson
18-18-22
FunctionalFunctional
Derivatives ofDerivatives of
Carboxylic AcidsCarboxylic Acids
18-18-33
Carboxyl DerivativesCarboxyl Derivatives
In this chapter, we study five classes of organic compounds• under the structural formula of each is a drawing to
help you see its relationship to the carboxyl group
H-NH2H-Cl H-OR'RC-OHO
H-OCR'O
RC=NHO H
RC-OHO
RC-OHO
RC-OHO
-H2O -H2O -H2O -H2O-H2O
RC NRCNH2
ORCClO
RCOR'O
RCOCR'O O
The enol ofan amide
An acidchloride
An esterAn acidanhydride
An amide A nitrile
18-18-44
Structure: Acid ChloridesStructure: Acid Chlorides
The functional group of an acid halide is an acyl group bonded to a halogen• the most common are the acid chlorides• to name, change the suffix -ic acid-ic acid to -yl halide-yl halide
CH3CClOO
RC-Cl
OCl
O
Cl
O
Benzoyl chlorideEthanoyl chloride(Acetyl chloride)
An acyl group
Hexanedioyl chloride(Adipoyl chloride)
18-18-55
Sulfonyl ChloridesSulfonyl Chlorides
• replacement of -OH in a sulfonic acid by -Cl gives a sulfonyl chloride
SOHH3C
O
O
CH3SOH
O
O
SClH3C
O
O
CH3SCl
O
O
Methanesulfonicacid
p-Toluenesulfonic acid
Methanesulfonyl chloride(Mesyl chloride, MsCl)
p-Toluenesulfonyl chloride (Tosyl chloride, TsCl)
18-18-66
Acid AnhydridesAcid Anhydrides
The functional group of an acid anhydride is two acyl groups bonded to an oxygen atom• the anhydride may be symmetrical (two identical acyl
groups) or mixed (two different acyl groups)• to name, replace acidacid of the parent acid by anhydrideanhydride
COC
O O
CH3COCCH3
O O
Benzoic anhydrideAcetic anhydride
18-18-77
Acid AnhydridesAcid Anhydrides
Cyclic anhydrides are named from the dicarboxylic acids from which they are derived
Maleic anhydride
O
O
OPhthalic
anhydrideSuccinic
anhydride
O
O
O
O
O
O
18-18-88
Phosphoric AnhydridesPhosphoric Anhydrides
A phosphoric anhydride contains two phosphoryl groups bonded to an oxygen atom
Triphosphoric acid
Diphosphate ion(Pyrophosphate ion)
Diphosphoric acid(Pyrophosphoric acid)
HO-P-O-P-OH-O-P-O-P-O-
HO-P-O-P-O-P-OH-O-P-O-P-O-P-O-
Triphosphate ion
OH
O
OH
O
O-
O
O-
O
O-
O
O-
O
O-
O
O-
O
O- O-
OO
18-18-99
Esters Esters
The functional group of an ester is an acyl group bonded to -OR or -OAr• name the alkyl or aryl group bonded to oxygen
followed by the name of the acid • change the suffix -ic acid-ic acid to -ate-ate
O
OEtO
O
OEtO
O
O
Ethyl ethanoate(Ethyl acetate)
Diethyl butanedioate(Diethyl succinate)
Isopropyl benzoate
18-18-1010
Esters Esters
Cyclic esters are called lactoneslactones• name the parent carboxylic acid, drop the suffix -ic -ic
acidacid and add -olactone-olactone
4-Butanolactone(γ-Butyrolactone)
3-Butanolactone(β-Butyrolactone)
γβ
αβ
α
O O
OO
H3C
23
12
1
3 4
6-Hexanolactone(ε-Caprolactone)
εδ
γ
βα
O
O2
134
5 6
18-18-1111
Esters of Phosphoric AcidEsters of Phosphoric Acid
• phosphoric acid forms mono-, di-, and triesters• name by giving the name of the alkyl or aryl group(s)
bonded to oxygen followed by the word phosphatephosphate• in more complex phosphoric esters, it is common to
name the organic molecule and then indicate the presence of the phosphoric ester by the word phosphatephosphate or the prefix phospho-phospho-
OCH3
CH3OPOH
OC-H
CH2-O-P-O-
CHO
HO
O-
O
N
HO
H3C
CH2O-P-O-
O-
CHO OCO-
CCH2
O P O-
O-
OO
Dimethylphosphate
Glyceraldehyde3-phosphate
Pyridoxal phosphate Phosphoenol-pyruvate
18-18-1212
AmidesAmides
The functional group of an amide is an acyl group bonded to a nitrogen atom• IUPAC: drop -oic acidoic acid from the name of the parent acid
and add -amide-amide• if the amide nitrogen is bonded to an alkyl or aryl
group, name the group and show its location on nitrogen by NN--
CH3CNH2
OCH3C-N
H
CH3
OH-C-N
CH3
CH3
O
N-Methylacetamide(a 2° amide)
Acetamide(a 1° amide)
N,N-Dimethyl-formamide (DMF)
(a 3° amide)
18-18-1313
AmidesAmides
Cyclic amides are called lactams• name the parent carboxylic acid, drop the suffix -ic -ic
acidacid and add -lactam-lactamα
β
γδ ε
6-Hexanolactam(ε-Caprolactam)
α
βH3C
O
NH
O
NH1
2 1
234
5 63
3-Butanolactam(β-Butyrolactam)
18-18-1414
PenicillinsPenicillins
• the penicillins are a family of β-lactam antibiotics
NH
H2N
HH
HO
N
S
COOHO
Amoxicillin(a β-lactam antibiotic)
The penicillinsdiffer in thegroup bondedto the acyl carbon
β-lactam
O
18-18-1515
CephalosporinsCephalosporins
• the cephalosporins are also β-lactam antibiotics
N
S
MeCOOH
O
O
NHNH2
HH
The cephalosporins differ in thegroup bonded to the acyl carbon andthe side chain of the thiazine ring
Cephalexin(Keflex)
β-lactam
18-18-1616
ImidesImides
The functional group of an imide is two acyl groups bonded to nitrogen• both succinimide and phthalimide are cyclic imides
PhthalimideSuccinimide
NH NH
O O
OO
18-18-1717
NitrilesNitriles
The functional group of a nitrile is a cyano group• IUPAC names: name as an alkanenitrilealkanenitrile• common names: drop the -ic acid-ic acid and add -onitrile-onitrile
CH3C N C N CH2C N
Ethanenitrile(Acetonitrile)
Benzonitrile Phenylethanenitrile(Phenylacetonitrile)
18-18-1818
Acidity of N-H bondsAcidity of N-H bonds
Amides are comparable in acidity to alcohols• water-insoluble amides do not react with NaOH or
other alkali metal hydroxides to form water-soluble salts
Sulfonamides and imides are more acidic than amides
CH3CNH2
O
O
O
SNH2 NH
O
O
NH
O
O
pKa 8.3pKa 9.7pKa 10PhthalimideSuccinimideBenzenesulfonamideAcetamide
pKa 15-17
18-18-1919
Acidity of N-H bondsAcidity of N-H bonds
Imides are more acidic than amides because 1. the electron-withdrawing inductive of the two adjacent
C=O groups weakens the N-H bond, and
2. the imide anion is stabilized by resonance delocalization of the negative charge
O
O
N N
O
O
A resonance-stabilized anion
N
O
O
18-18-2020
Acidity of N-HAcidity of N-H
• imides such as phthalimide readily dissolve in aqueous NaOH as water-soluble salts
(stronger acid)
(weakeracid)
(weakerbase)
(strongerbase)
pKa 15.7pKa 8.3
++
O
O
NH N- Na+
O
O
NaOH H2O
18-18-2121
Characteristic ReactionsCharacteristic Reactions
Nucleophilic acyl substitution:Nucleophilic acyl substitution: an addition-elimination sequence resulting in substitution of one nucleophile for another
Tetrahedral carbonyladdition intermediate
-
++ CNuR
CY R
CNuR
O
Y
O O
:Nu- :Y-
Substitution product
:
18-18-2222
Characteristic ReactionsCharacteristic Reactions
• in the general reaction, we showed the leaving group as an anion to illustrate an important point about them: the weaker the base, the better the leaving group
R2N- RO-
O
RCO- X-
Increasing basicity
Increasing leaving ability
18-18-2323
Characteristic ReactionsCharacteristic Reactions
• halide ion is the weakest base and the best leaving group; acid halides are the most reactive toward nucleophilic acyl substitution
• amide ion is the strongest base and the poorest leaving group; amides are the least reactive toward nucleophilic acyl substitution
18-18-2424
Reaction with HReaction with H22O - Acid ChloridesO - Acid Chlorides
• low-molecular-weight acid chlorides react rapidly with water
• higher molecular-weight acid chlorides are less soluble in water and react less readily
CH3CClO
H2O CH3COHO
HCl++
Acetyl chloride
18-18-2525
Reaction with HReaction with H22O - AnhydridesO - Anhydrides
• low-molecular-weight acid anhydrides react readily with water to give two molecules of carboxylic acid
• higher-molecular-weight acid anhydrides also react with water, but less readily
CH3COCCH3
O OH2O CH3COH
OHOCCH3
O++
Acetic anhydride
18-18-2626
Reaction with HReaction with H22O - AnhydridesO - Anhydrides
• Step 1: addition of H2O to give a TCAI
• Step 2: protonation followed collapse of the TCAI
O
CH3-C-O-C-CH3
H
H
O-H
O
O HH
CH3 -C-O-C-CH3
H
H
O-H
CH3 -C-O-C-CH3
O
OH
H
H-O-H
H
++
+
Tetrahedral carbonyladdition intermediate
+
OO
O
CH3-C-O-C-CH3
O
HOH
H+ O
H H
CH3 C
O
O
O C
O
CH3
H
HOH
H+
CH3 C O
O
O
C CH3
OH
H
H
H
H+ H
+O
18-18-2727
Reaction with HReaction with H22O - EstersO - Esters
Esters are hydrolyzed only slowly, even in boiling water• hydrolysis becomes more rapid if they are heated with
either aqueous acid or base
Hydrolysis in aqueous acid is the reverse of Fischer esterification• the role of the acid catalyst is to protonate the
carbonyl oxygen and increase its electrophilic character toward attack by water (a weak nucleophile) to form a tetrahedral carbonyl addition intermediate
• collapse of this intermediate gives the carboxylic acid and alcohol
18-18-2828
Reaction with HReaction with H22O - EstersO - Esters
Acid-catalyzed ester hydrolysis
R OCH3
CO
H2OH+
OHC
ROCH3
OHH+
R OHCO
CH3OH+ +
Tetrahedral carbonyladdition intermediate
18-18-2929
Reaction with HReaction with H22O - EstersO - Esters
Hydrolysis of an esters in aqueous base is often called saponificationsaponification• each mole of ester hydrolyzed requires 1 mole of base• for this reason, ester hydrolysis in aqueous base is
said to be base promoted
• hydrolysis of an ester in aqueous base involves formation of a tetrahedral carbonyl addition intermediate followed by its collapse and proton transfer
O
RCOCH3 NaOHH2O
O
RCO- Na
+ CH3OH++
18-18-3030
Reaction with HReaction with H22O - EstersO - Esters
• Step 1: attack of hydroxide ion (a nucleophile) on the carbonyl carbon (an electrophile)
• Step 2: collapse of the TCAI• Step 3: proton transfer to the alkoxide ion; this step is
irreversible and drives saponification to completion
R-C-OCH3
O
OH R-CO
OH
OCH3R-C
O
OH
OCH3 R-CO
O
HOCH3
(1)+
(2) (3)+ +
18-18-3131
Reaction with HReaction with H22O - AmidesO - Amides
Hydrolysis of an amide in aqueous acid requires 1 mole of acid per mole of amide• reaction is driven to completion by the acid-base
reaction between the amine or ammonia and the acid
2-Phenylbutanoic acid2-Phenylbutanamide
++ +heat
H2 O HClH2 O
NH4+ Cl
-
PhNH2
O
PhOH
O
18-18-3232
Reaction with HReaction with H22O - AmidesO - Amides
Hydrolysis of an amide in aqueous base requires 1 mole of base per mole of amide• reaction is driven to completion by the irreversible
formation of the carboxylate sale
CH3CNH
O
NaOHH2O
CH3CO-Na+
OH2N
AnilineSodiumacetate
N-Phenylethanamide(N-Phenylacetamide, Acetanilide)
++heat
18-18-3333
Reaction with HReaction with H22O - AmidesO - Amides
• Step1: protonation of the carbonyl oxygen gives a resonance-stabilized cation intermediate
R C
O
NH2 OH H
H
O
C NH2R
HO
C NH2R
H
C
O
NH2R
H
H2O
Resonance-stabilized cation intermediate
+
+
++
++
18-18-3434
Reaction with HReaction with H22O - AmidesO - Amides
• Step 2: addition of water (a nucleophile) to the carbonyl carbon (an electrophile) followed by proton transfer gives a TCAI
• Step 3: collapse of the TCAI and proton transfer
++ O
H
H C
OH
NH2R
OH H
C
OH
NH3+R
O
+C
OH
NH2R
H
proton transfer from
O to N
R C
OH
C OHRNH3
H
C
O
NH3+R
OH
NH4+++
O+
OH
18-18-3535
Reaction with HReaction with H22O - NitrilesO - Nitriles
The cyano group is hydrolyzed in aqueous acid to a carboxyl group and ammonium ion
• protonation of the cyano nitrogen gives a cation that reacts with water to give an imidic acid
• keto-enol tautomerism gives the amide
Ph CH2C N 2H2O H2SO4H2O
Ph CH2COH
O
NH4+HSO4
-
Ammoniumhydrogen sulfate
Phenylaceticacid
Phenylacetonitrile
+heat
++
R-C N H2O H+
NH
OH
R-C R-C-NH2
O
An imidic acid(enol of an amide)
+
An amide
18-18-3636
Reaction with HReaction with H22O - NitrilesO - Nitriles
• hydrolysis of a cyano group in aqueous base gives a carboxylic anion and ammonia; acidification converts the carboxylic anion to the carboxylic acid
CH3(CH2)9C NNaOH, H2O
O
CH3(CH2)9COH
CH3(CH2)9CO-Na
+O
HCl H2O
NaCl
NH3
NH4Cl
Sodium undecanoate Undecanenitrile
+heat
Undecanoic acid
+ +
18-18-3737
Reaction with HReaction with H22O - NitrilesO - Nitriles
• hydrolysis of nitriles is a valuable route to carboxylic acids
CH3(CH2)8CH2ClKCN
CH3(CH2)9C NH2SO4, H2O
CH3(CH2)9COH
O
Undecanenitrileheat
Undecanoic acid1-Chlorodecane ethanol, water
CHO HCN, KCN CN
OH
H2SO4, H2O COOH
OH
heat
Benzaldehyde Benzaldehyde cyanohydrin(Mandelonitrile)
(racemic)
2-Hydroxyphenylacetic acid(Mandelic acid)
(racemic)
ethanol,water
18-18-3838
Reaction with AlcoholsReaction with Alcohols
Acid halides react with alcohols to give esters• acid halides are so reactive toward even weak
nucleophiles such as alcohols that no catalyst is necessary
• where the alcohol or resulting ester is sensitive to HCl, reaction is carried out in the presence of a 3° amine to neutralize the acid
Butanoylchloride
Cyclohexyl butanoate
+
Cyclohexanol
HO HClCl
O
+ O
O
18-18-3939
Reaction with AlcoholsReaction with Alcohols
• sulfonic acid esters are prepared by the reaction of an alkane- or arenesulfonyl chloride (Section 18.1A) with an alcohol or phenol
• the key point here is that OH- (a poor leaving group) is transformed into a sulfonic ester (a good leaving group) with retention of configuration at the chiral center
OH
TsCl
OTs
(R)-2-Octanol p-Toluenesulfonylchloride
(Tosyl chloride)
(R)-2-Octyl p-toluenesulfonate[(R)-2-Octyl tosylate]
+ pyridine
18-18-4040
Reaction with AlcoholsReaction with Alcohols
Acid anhydrides react with alcohols to give one mole of ester and one mole of carboxylic acid
• cyclic anhydrides react with alcohols to give one ester group and one carboxyl group
CH3COCCH3
OHOCH2CH3 CH3COCH2CH3
OCH3COH
O
Acetic acidEthyl acetateEthanolAcetic anhydride++
(sec-Butyl hydrogenphthalate
2-Butanol(sec-Butyl alcohol)
+
Phthalicanhydride
O
O
O
OOHHO
O
O
18-18-4141
Reaction with AlcoholsReaction with Alcohols
• aspirin is synthesized by treating salicylic acid with acetic anhydride
Acetylsalicylic acid (Aspirin)
2-Hydroxybenzoic acid
(Salicylic acid)
+
+
Acetic acid
Acetic anhydride
CH3COH
CH3COCCH3
OOCOOH
CH3
O
OHCOOH
O O
18-18-4242
Reaction with AlcoholsReaction with Alcohols
Esters react with alcohols in the presence of an acid catalyst in an equilibrium reaction called transesterificationtransesterification
Butyl propenoate(Butyl acrylate)
(bp 147°C)
1-Butanol(bp 117°C)
Methyl propenoate(Methyl acrylate)
(bp 81°C)
+
+ HCl
CH3OHMethanol(bp 65°C)
OCH3
O
HO
O
O
18-18-4343
Reaction with Ammonia, etc.Reaction with Ammonia, etc.
Acid halides react with ammonia, 1° amines, and 2° amines to form amides• 2 moles of the amine are required per mole of acid
chloride
Cl
O
2NH3 NH2
O
NH4+Cl
-+ +
Hexanoylchloride
Ammonia Hexanamide Ammoniumchloride
18-18-4444
Reaction with Ammonia, etc.Reaction with Ammonia, etc.
Acid anhydrides react with ammonia, and 1° and 2° amines to form amides• 2 moles of ammonia or amine are required
CH3COCCH3
O O2NH3 CH3CNH2
OCH3CO-NH4
+O
+ +
Aceticanhydride
Ammonia Acetamide Ammoniumacetate
18-18-4545
Reaction with Ammonia, etc.Reaction with Ammonia, etc.
Esters react with ammonia, and 1° and 2° amines to form amides• esters are less reactive than either acid halides or acid
anhydrides
Amides do not react with ammonia, or 1° or 2° amines
PhOEt
O
NH3Ph
NH2
O
EtOH
PhenylacetamideEthyl phenylacetate
+ +
Ethanol
18-18-4646
Acid Chlorides with SaltsAcid Chlorides with Salts
Acid chlorides react with salts of carboxylic acids to give anhydrides • most commonly used are sodium or potassium salts
+
Acetyl chloride
Sodium benzoate Acetic benzoicanhydride
+CH3 CCl -OC CH3 COC Na+Cl -Na+O O O O
18-18-4747
InterconversionsInterconversions
18-18-4848
Reaction with Grignard ReagentsReaction with Grignard Reagents
• treating a formic ester with 2 moles of Grignard reagent followed by hydrolysis in aqueous acid gives a 2° alcohol
HCOCH3
O2RMgX
H2O, HClHC-R
R
OHCH3OH+
magnesium alkoxide salt
A 2° alcoholAn ester offormic acid
+
18-18-4949
Reaction with Grignard ReagentsReaction with Grignard Reagents
• treating an ester other than formic with a Grignard reagent followed by hydrolysis in aqueous acid gives a 3° alcohol
CH3COCH3
O2RMgX
H2O, HClCH3C-R
R
OHCH3OH
magnesium alkoxide salt
+
A 3° alcohol An ester of any acidother than formic acid
+
18-18-5050
Reaction with Grignard ReagentsReaction with Grignard Reagents
1. addition of 1 mole of RMgX to the carbonyl carbon gives a TCAI
2. collapse of the TCAI gives a ketone (an aldehyde from a formic ester)
O
CH3-C-OCH3 R MgX
O
R
OCH3CH3-C
[MgX]+
CH3-C
R
O
CH3O -[MgX]
+
1
1
+
-
+
A magnesium salt(a tetrahedral carbonyladdition intermediate)
A ketone
2
2
18-18-5151
Reaction with Grignard ReagentsReaction with Grignard Reagents
3. reaction of the ketone with a 2nd mole of RMgX gives a second TCAI
4. treatment with aqueous acid gives the alcohol
CH3-C
O
R
R MgX CH3-C-R
R
O - [MgX]
+
H2O, HClCH3-C-R
R
OH
Magnesium saltA ketone
+
A 3° alcohol
33
(4)
18-18-5252
Reactions with RLiReactions with RLi
Organolithium compounds are even more powerful nucleophiles than Grignard reagents• they react with esters to give the same types of 2° and
3° alcohols as do Grignard reagents• and often in higher yields
RCOCH3
1. 2R'Li
2. H2O, HClR-C-R'
O
R'
OH
+ CH3OH
18-18-5353
Gilman ReagentsGilman Reagents
Acid chlorides at -78°C react with Gilman reagents to give ketones • under these conditions, the TCAI is stable, and it is not
until acid hydrolysis that the ketone is liberated
1. (CH3)2CuLi, ether, -78°C
2. H2OPentanoyl chloride 2-Hexanone
Cl
O O
18-18-5454
Gilman ReagentsGilman Reagents
• Gilman reagents react only with acid chlorides• they do not react with acid anhydrides, esters, amides,
or nitriles under the conditions described
1. (CH3)2CuLi, ether, -78°C
2. H2OO
H3COCl
O
O
H3COO
18-18-5555
Reduction - Esters by LiAlHReduction - Esters by LiAlH44
Most reductions of carbonyl compounds now use hydride reducing agents• esters are reduced by LiAlH4 to two alcohols
• the alcohol derived from the carbonyl group is primary
Methanol2-Phenyl-1-propanolMethyl 2-phenyl-
propanoate
+1. LiAlH4 , ether
2. H2O, HCl
CH3OHPhOCH3
O PhOH
18-18-5656
Reduction - Esters by LiAlHReduction - Esters by LiAlH44
Reduction occurs in three steps plus workup• Steps 1 and 2 reduce the ester to an aldehyde
• Step 3 reduction of the aldehyde followed by work up gives a 1° alcohol
A tetrahedral carbonyladdition intermediate
(1)R C OR'
O
+ H R C OR'
O
HR C
H
O(2)
OR'+
A 1° alcohol
R C
H
O+ H
(3)R C H
O
H
(4)R C H
OH
H
18-18-5757
Reduction - Esters by NaBHReduction - Esters by NaBH44
NaBH4 does not normally reduce esters, but it does reduce aldehydes and ketones
Selective reduction is often possible by the proper choice of reducing agents and experimental conditions
OEt
O O NaBH4
EtOH OEt
OH O
(racemic)
18-18-5858
Reduction - Esters by DIBAlHReduction - Esters by DIBAlH
Diisobutylaluminum hydride (DIBAlH) at -78°C selectively reduces an ester to an aldehyde• at -78°C, the TCAI does not collapse and it is not until
hydrolysis in aqueous acid that the carbonyl group of the aldehyde is liberated
Hexanal
Methyl hexanoate
+
1. DIBALH, toluene, -78°C
2. H2O, HCl
CH3OH
OCH3
O
H
O
18-18-5959
Reduction - Amides by LiAlHReduction - Amides by LiAlH44
LiAlH4 reduction of an amide gives a 1°, 2°, or 3° amine, depending on the degree of substitution of the amide
NH2
O1. LiAlH42. H2O
1. LiAlH4
2. H2ONMe2
ONMe2
NH2
Octanamide 1-Octanamine
N,N-Dimethylbenzamide N,N-Dimethylbenzylamine
18-18-6060
Reduction - Amides by LiAlHReduction - Amides by LiAlH44
The mechanism is divided into 4 steps• Step 1: transfer of a hydride ion to the carbonyl carbon• Step 2: a Lewis acid-base reaction and formation of an
oxygen-aluminum bond
R C NH2
O
+H AlH3 R C NH2
O
HAlH3
(1)R C NH2
O
H
(2)AlH3
+
18-18-6161
Reduction - Amides by LiAlHReduction - Amides by LiAlH44
• Step 3: redistribution of electrons and ejection of H3AlO- gives an iminium ion
• Step 4: transfer of a second hydride ion to the iminium ion completes the reduction to the amine
R C N
O
H
AlH3
HH
H
R C NH
HH
R-CH2-NH2
An iminium ion
(3) (4)
A 1° amine
18-18-6262
Reduction - Nitriles by LiAlHReduction - Nitriles by LiAlH44
The cyano group of a nitrile is reduced by LiAlH4 to a 1° amine
6-Octenenitrile
6-Octen-1-amine
CH3CH=CH(CH2)4C1. LiAlH4
2. H2O
CH3CH=CH(CH2)4CH2NH2
N
18-18-6363
InterconversionsInterconversions
Problem:Problem: show reagents and experimental conditions to bring about each reaction
PhOH
O
OMe
OPh
PhOH
PhCl
O
PhNH2
PhNH2
O
Phenylacetic acid
(a) (b) (c)
(d) (e)
(f)
(g) (h)
18-18-6464
Derivatives of Derivatives of
Carboxylic AcidsCarboxylic Acids
End Chapter 18End Chapter 18