a2 chemistry carboxylic acids and their derivatives
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7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B1
A2 chemistryCarboxylic Acids
and their Derivatives35.135.1 ntro!"#tionntro!"#tion
35.$35.$ Nomen#lat"re of Car%o&yli# A#i!s an! their Nomen#lat"re of Car%o&yli# A#i!s an! their'erivatives'erivatives
35.335.3 (hysi#al (ro)erties of Car%o&yli# A#i!s(hysi#al (ro)erties of Car%o&yli# A#i!s
35.*35.* (re)aration of Car%o&yli# A#i!s(re)aration of Car%o&yli# A#i!s35.535.5 +ea#tions of Car%o&yli# A#i!s+ea#tions of Car%o&yli# A#i!s
35.,35., +ea#tions of the 'erivatives of Car%o&yli# A#i!s+ea#tions of the 'erivatives of Car%o&yli# A#i!s
35.35. ses of Car%o&yli# A#i!s an! their 'eri vati vesses of Car%o&yli# A#i!s an! their 'eri vativ es
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/eneral form"la of #ar%o&yli# a#i!0 RCOOH
Examples:
AS recap
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Name StructureA#yl#hlori!es
A#i!anhy!ri!es
Ami!es
sters
Carboxylic acid derivatives
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Nomenclature of Carboxylic Acids and their Derivatives
Car%o&yli# a#i!s are name! %y replacing the final “-e” ofthe name of the corresponding alkane with “-oic acid”
When other s"%stit"ents are )resent2 the carbox l carbon isassigned position !
Examples:
Carboxylic Acids
Carboxylic Acids
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New Way Chemistry for Hong Kong A-Level Book 3B5
A#yl #hlori!es are name! %y replacing the final “-ic acid”of the name of the parent carbox lic acid with “- l
chloride”
Examples:
Acyl Chlorides
Acyl Chlorides
Nomenclature of Carboxylic Acids and their Derivatives
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A#i! anhy!ri!es are name! %y dropping the word “acid”from the name of the parent carbox lic acid an! thenadding the word “anh dride”
Examples:
Acid Anhydrides
Acid Anhydrides
Nomenclature of Carboxylic Acids and their Derivatives
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Ami!es that have no s"%stit"ents on the nitrogen atom are name!
%yreplacing “-oic acid” from the parent carbox lic acid with“amide”
4"%stit"ents on the nitrogen atom of ami!es are name! an! thename! s"%stit"ent is )re#e!e! %y N -" or N " N -
Examples:
Amides Amides
Nomenclature of Carboxylic Acids and their Derivatives
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6he names of esters are !erive! from the names of the
al#ohol 7with the en!ing “- l” 8 an! the #ar%o&yli# a#i! 7withthe en!ing “-oate” 8
6he )ortion of the name !erive! from the al#ohol #omes first
Examples:
Esters Esters
Nomenclature of Carboxylic Acids and their Derivatives
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Tutorial Question 1Tutorial Question 1#i$e the %&'(C names of the following compounds)
*a+
*b+
*c+
*d+
Answer
Solution:
(a) 3-Methylbutanoic acid
(b) N -methylethanamide
(c) Ethyl benzoate
(d) Benzoic anhydride
Nomenclature of Carboxylic Acids and their Derivatives
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Tutorial Question 2Tutorial Question 2(n ester is formed b reacting an alcohol with a carbox licacid, raw the structural formula of the following estermolecule and gi$e the name of the alcohol and thecarbox lic acid that form the ester,
*a+ .eth l ethanoateAnswer Solution:
(a) The structural formula of methyl ethanoate is
!t is formed from the reaction of ethanoic acid andmethanol"
Nomenclature of Carboxylic Acids and their Derivatives
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Example !"2Exam ple !"2(n ester is formed b reacting an alcohol with acarbox lic acid, raw the structural formula of thefollowing ester molecule and gi$e the name of the alcoholand the carbox lic acid that form the ester,
*b+ /th l methanoateAnswer
Solution:
(b) The structural formula of ethyl methanoate is
!t is formed from the reaction of methanoic acidand ethanol"
Nomenclature of Carboxylic Acids and their Derivatives
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Chec# $oint !"1Chec# $oint !"1Complete the following table b filling in the molecularformulae" structural formulae or %&'(C names of thecarbox lic acids,
Answer
;ole#"lar form"la 4tr"#t"ral form"la (AC name
C3H C<<H 7a8 7%8
7#8 7!8
7e8 7f8
7g8 7h8 6ri#hloroethanoi# a#i!
7a8
7%8 B"tanoi# a#i! 7#8 CH3CH7CH
38CH
$C<<H
7!8 3-;ethyl%"tanoi# a#i!
7e8 C, H*ClC<<H 7f8 $-Chloro%en=oi# a#i!
7g8 CCl3C<<H
7h8
Nomenclature of Carboxylic Acids and their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B13
!0 and 10 alk l groups 7%"t not 3>8directl attached to aben2ene ring are o&i!i=e! %y hot K;n< *?<H @ to #ar%o&yl gro")e.g.
Oxidation of AlkybenzenesOxidation of Alkybenzenes
!%& #re$aration of Carboxylic Acids %&B $"3'(
6his o&i!ation takes )la#e initially at the ben2 lic carbon alkyl gro")s longer than methyl gro") are "ltimately
!egra!e! to %en=oi# a#i!
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6he a#i! strength of ethanoi# a#i! is shown %y the val"e of its
acid dissociation constant *3 a+
C<<HCH<HC<<CH
K 3
33a
+
=
-
p3 a is "se! for #onvenien#e as K
a is small for weak a#i!s
p3 a 4 5log 3 a 2the smaller the p3 a $alue" the stronger is the acid
p3 a is "se! for #onvenien#e as K a is small for weak a#i!s
3 a 4 !6-p3a
smaller the p3 a $alue" the stronger is the acid
ethanoic acid
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New Way Chemistry for Hong Kong A-Level Book 3B15
Car%o&yli# a#i!s are stronger a#i!s than
al#ohol %e#a"se(oint 1a86he #ar%onyl gro") weakens the <-H %on! ..thismeans
6he very ele#tronegative o&ygen in Car%onyl gro") has anele#tron with!rawing effe#t an! )olari=es the <-H %on!.(oint $
%8 #ar%o&ylate ion is sta%ili=e! %y the !elo#ali=ation ofele#tron aro"n! the #ar%o&ylate ion this means6he negative #harge is s)rea! o"t in the #ar%o&ylate ionan! is less likely to attra#t the hy!rogen ion.
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6he greater sta%ility of #ar%o&yli# a#i!s is attri%"te! toresonance stabili2ation of the carbox late ions
&am)le0
Resonance Effect
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p3 a is "se! for #onvenien#e as K a is small for weak a#i!s
p3 a 4 5log 3 a 2the smaller the p3 a $alue" the stronger is the acidp3 a is "se! for #onvenien#e as K a is small for weak a#i!s
3 a 4 !6 -p3a
7he smaller the p3 a and larger the 3 a$alue" the stronger is the
acid
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p3 a increases and acid becomes weaker when no of C
and H atoms in molecule increases,
(lk l groups are electron donating groups that makes
the O-H bond stronger and less h drogen ions are
released from carbox lic acid,
Name 8ormula p3 a
;ethanoi# a#i!
thanoi# a#i!
(ro)anoi# a#i!
B"tanoi# a#i!
Ben=oi# a#i!
HC<<H
CH 3C<<HCH 3CH $C<<H
CH 3CH $CH $C<<H
C , H5C<<H
3. 5
*. ,
*.
*. $
*.$:
ns"%stit"te! #ar%o&yli# a#i!
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New Way Chemistry for Hong Kong A-Level Book 3B19
By the resonan#e effe#t2 the ethanoate ion #an %esta%ili=e! %y spreading the negati$e charge o$er two
ox gen atoms
!%! )eactions of Carboxylic Acids %&B $"*+(
No stabili2ing resonance structures for alkoxide ions e.g.
Carbox lic acids are much acidic than alcohols formation of more stable con9ugate base
f $
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Both #om)o"n!s #ontain the highl polari2ed O 5 Hbond !"e to the difference in electronegati$it
6he greater acidit of ethanoic acid is !"e to the )resen#e of the )owerf"l electron-withdrawing carbon lgroup
!%! )eactions of Carboxylic Acids %&B $"*+(
Inductive Effect
% ) i f C b li A id %& $ (
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6he carbon l atom of ethanoi# a#i! %ears a large
partial positi$e charge an! e&erts a powerful electron-withdrawing inducti$e effect to hy!ro&yl o&ygen atom2making the h drox l h drogen atom much morepositi$e
proton dissociate more readil
6he electron-withdrawing inducti$e effect of thecarbon l group stabili2es the carbox late ion
carbox lic acids are stronger acid than alcoho ls
!%! )eactions of Carboxylic Acids %&B $"*+(
6wo resonance structures for the #ar%onyl gro")0
!%! ) i f C b li A id %&B $"* (
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1. Electron-withdrawin !ro"ps
7he presence of electron-withdrawing groups increasethe acidit of a carbox lic acide.g.
!%! )eactions of Carboxylic Acids %&B $"*,(
Inductive Efects o OtherGroups
!%! ) i f C b li A id %&B $"* (
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New Way Chemistry for Hong Kong A-Level Book 3B$3
6he chlorine atom with!raws ele#tron from the #ar%onyl
gro") an! o&ygen making the h drox l h drogen morepositi$e than that of ethanoi# a#i!
!%! )eactions of Carboxylic Acids %&B $"*,(
6he #hlorine atom also stabili2es the #hloroethanoate ionto greater e&tent
!%! ) ti f C b li A id %&B $"*+(
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!%! )eactions of Carboxylic Acids %&B $"*+(
CH 3C<<H D D D D
thanoi# o!oethanoi# Bromoethanoi# Chloroethanoi#El"oroethanoi#
a#i! a#i! a#i! a#i! a#i!*. , 3.1 $.9: $. , $.,,
A#i!ity
)K a
CH 3C<<H D D D CCl 3C<<H
thanoi# Chloroethanoi# 'i#hloroethanoi# 6ri#hloroethanoi#a#i! a#i! a#i! a#i!*. , $. , 1.$9 :.,5
A#i!ity
)K a
Effect of electron-withdrawing substituents on the acidity of carboxylic acids
7he greater the number of electron-withdrawing groups" thestronger is the acid
7he more electronegati$e of halogen substituents *8 : Cl :
;r : %+" the stronger is the acid
!%! ) ti f C b li A id %&B $"*3(
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!%! )eactions of Carboxylic Acids %&B $"*3(
6he f"rther away of the s"%stit"ents from the #ar%o&yl
gro")2 the weaker is the a#i!
D D
*-Chloro%"tanoi# 3-Chloro%"tanoi# $-Chloro%"tanoi#a#i! a#i! a#i!*.5$ *.:, $. *
A#i!ity
)K a
!%! ) ti f C b li A id %&B $"*3(
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#. Electron-releasin !ro"ps
7he presence of electron-releasing groups reduce theacidit of a carbox lic acide.g.
!%! )eactions of Carboxylic Acids %&B $"*3(
!%! )eactions of Carboxylic Acids %&B $"*3(
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!%! )eactions of Carboxylic Acids %&B $"*3(
le#tron-releasing alkyl gro")s release electrons towar!s theelectron-deficient carbon l carbon 2 th"s re!"#ing its #harge
Reduce the positi$e character of the h drox lh drogen atom
dissociate less readil
%ntensif the negati$e charge on the #ar%o&yl gro") destabli2es the ethanoate ion
!%! )eactions of Carboxylic Acids %&B $"**(
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Chec# $oint !"Chec# $oint !"
*a+ .atch the 3 a $alues) 1,!< !6 5=
. and !,1> !6 5=
."to the carbox lic acids) CH 18COOH and
CH 1;rCOOH, /xplain our answer briefl ,
Answer
!%! )eactions of Carboxylic Acids %&B $ **(
7a8 6he greater the K a val"e2 the stronger is the a#i!.
CH $EC<<H is a stronger a#i! than CH $BrC<<H.6his @E s"%stit"ent e&erts a stronger in!"#tive effe#tthan the @Br s"%stit"ent2 as fl"orine is moreele#tronegative than %romine. 6he @E s"%stit"entsta%ili=es the #onF"gate %ase 7i.e. CH $EC<<H @ 8 to a
greater e&tent than the @Br s"%stit"ent. 6herefore2CH $EC<<H has a K a val"e of $.19 × 1: @3 ;2 an!CH $BrC<<H has a K a val"e of 1.$, × 1: @3 ;.
!%! )eactions of Carboxylic Acids %&B $"**(
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Chec# $oint !"Chec# $oint !"
*b+ (rrange the following acids in ascending order of acidit )CHCl 1COOH" CCl =COOH" CH 1ClCOOH" CH =COOH
/xplain the order briefl ,Answer
!%! )eactions of Carboxylic Acids %&B $ **(
7%8 CH3C<<H D CH $ClC<<H D CHCl $C<<HD CCl3C<<H
6he @Cl s"%stit"ent is an ele#tron-with!rawinggro"). An in#reasing n"m%er of the @Cl s"%stit"ent
%rings a%o"t a greater negative in!"#tive effe#t.6h"s2 the #onF"gate %ase will %e sta%ili=e! more2an! the a#i!ity of the a#i! in#reases.
!%! )eactions of Carboxylic Acids %&B $"**(
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Chec# $oint !"Chec# $oint !"
*c+ (rrange the following ar l carbox lic acids in descendingorder of acidit )
/xplain the order briefl ,
!%! )eactions of Carboxylic Acids %&B $ **(
!%! )eactions of Carboxylic Acids %&B $"**(
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!%! )eactions of Carboxylic Acids %&B $ **(
7#8
is more a#i!i# than 2%e#a"se #ontains
the @Cl s"%stit"ent whi#h is an ele#tron-with!rawing gro"). 6h"s2 ite&erts a negative in!"#tive effe#t to the #onF"gate %ase2 an! hen#e
sta%ili=es the #ar%o&ylate ion forme!.
is less a#i!i# than 2 %e#a"se #ontains
a methyl gro") whi#h is an ele#tron-releasing gro"). 6h"s2 it e&erts a )ositive in!"#tive effe#t to the #onF"gate %ase2 an! hen#e !esta%ili=esthe #ar%o&ylate ion forme!.
!%! )eactions of Carboxylic Acids %&B $"**(
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Chec# $oint !"Chec# $oint !"
*d+ ?hich is a stronger acid" CH 1ClCOOH orCH =CHClCOOH@ /xplain our answer briefl ,
Answer
!%! )eactions of Carboxylic Acids %&B $ (
7!8 CH$ClC<<H is a stronger a#i! as CH 3CHClC<<H#ontains a methyl gro") whi#h is an ele#tron-releasinggro"). t e&hi%its a )ositive in!"#tive effe#t an! th"s!esta%ili=es the #onF"gate %ase of the a#i!. 6herefore2CH 3CHClC<<H is less a#i!i#.
!%! )eactions of Carboxylic Acids %&B $"**(
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New Way Chemistry for Hong Kong A-Level Book 3B33
Car%o&yli# a#i!s rea#t with reacti$e metals s"#h as Naor ;g to give the #orres)on!ing metal carbox lates an!h drogen gas
$ormation of %alts$ormation of %alts
!%! )eactions of Carboxylic Acids %&B $ (
Reaction with Active Metals
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Example:
!%! )eactions of Carboxylic Acids %&B $"* (
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New Way Chemistry for Hong Kong A-Level Book 3B35
Car%o&yli# a#i!s rea#t with strong alkalis such as NaOH toform sodium carbox lates an! water
!%! )eactions of Carboxylic Acids %&B $ (
Reaction with Bases
Examples:
!%! )eactions of Carboxylic Acids %&B $"* (
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Car%o&yli# a#i!s also rea#t weak alkalis such as Na 1CO = or
NaHCO = to form sodium carbox lates 2carbon dioxide an!water
!%! )eactions of Carboxylic Acids %&B $ (
!%! )eactions of Carboxylic Acids %&B $"* (
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6his rea#tion serves as a test to distinguish carbox lic acidsand other acidic organic compounds
Examples:
!%! )eactions of Carboxylic Acids %&B $ (
!%! )eactions of Carboxylic Acids %&B $"*.(
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!%! )eactions of Carboxylic Acids %&B $ .(
NaOH an!Na 1CO = #an %e"se! to se)arate ami&t"re ofal#ohols2 )henolsan! #ar%o&yli#a#i!s
!%! )eactions of Carboxylic Acids %&B $"*.(
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New Way Chemistry for Hong Kong A-Level Book 3B39
Chec# $oint !"&Chec# $oint !"&
*a+ escribe how to separate a mixture of ben2oic acidand phenol in the laborator ,
Answer
!%! )eactions of Carboxylic Acids %&B $ .(
7a8 4o!i"m hy!rogen#ar%onate2 water an! !iethyl ether are
a!!e! to the mi&t"re. Ben=oi# a#i! rea#ts with so!i"mhy!rogen#ar%onate to form a water-sol"%le salt whi#h!issolves in the aG"eo"s layer. After se)aration %y the "seof a se)arating f"nnel2 )henol #an %e re#overe! %y !istillingoff the ether. 6o the aG"eo"s layer2 hy!ro#hlori# a#i! is
a!!e! to generate the %en=oi# a#i! whi#h #an %e e&tra#te! %y !iethyl ether. After se)aration from the aG"eo"s
layer2 %en=oi# a#i! is o%taine! %y !istilling off theether.
!%! )eactions of Carboxylic Acids %&B $"*.(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*:
Chec# $oint !"&Chec# $oint !"&
*b+ Outline how a mixture of butanone and ethanoicacid can be separated in the laborator ,
Answer
) y $ (
!%! )eactions of Carboxylic Acids %&B $"*.(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*1
) y $ (
*b+
!%! )eactions of Carboxylic Acids %&B $"*/(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*$
(c l chlorides are the most reacti$e amongst the#ar%o&yli# a#i! !erivatives
6hey #an %e )re)are! %y the "se of SOCl 12'Cl = or'Cl A in goo! yiel!s
$ormation of Acyl Chlorides$ormation of Acyl Chlorides
) y (
!%! )eactions of Carboxylic Acids %&B $"*/(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*3
A#yl #hlori!es #an %e "se! to )re)are aldeh des 2ketones 2
esters 2amides an! acid anh drides in organi# synthesis
) y (
A#yl #hlori!es are e&tremely sensiti$e to moisture 2
therefore2 it m"st %e stored in anh drous conditions
h drol 2e rapidl to form carbox lic acids
!%! )eactions of Carboxylic Acids %&B $"*/(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B**
A#i! anhy!ri!es #an %e )re)are! %y reacting ac lchlorides with carbox lic acids in the presence ofp ridine
6his #an %e "se! to )re)are mixed anh drides 7+ ≠ + 8or simple anh drides 7+ I + 8
$ormation of Acid Anhydrides$ormation of Acid Anhydrides
) y (
!%! )eactions of Carboxylic Acids %&B $"*/(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*5
(c l chlorides react with sodium salts of carbox lic
acids to give a#i! anhy!ri!es
) y (
!%! )eactions of Carboxylic Acids %&B $"*0(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*,
Ammonia rea#ts with #ar%o&yli# a#i!s to form ammoni"msalts. 6he !ry salts are heate! to !ehy!rate to give ami!e
$ormation of Amides$ormation of Amides
6he %etter way to )re)are ami!es is reactingammonia or amines with ac l chlorides
!%! )eactions of Carboxylic Acids %&B $"*0(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*
Car%o&yli# a#i!s rea#t with al#ohols to form estersthro"gh condensation reactions
sterifi#ation rea#tions are acid-catal 2ed an!
re$ersible
$ormation of Esters$ormation of Esters
!%! )eactions of Carboxylic Acids %&B $"*0(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*
LiAlH * is a powerful reducing agent whi#h re!"#escarbox lic acids to primar alcohols in goo! yiel!s
&ed"ction with 'ithi"m (etrahydridoal"minate &ed"ction with 'ithi"m (etrahydridoal"minate
Example:
!%! )eactions of Carboxylic Acids %&B $"*'(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B*9
Example !"&Exam ple !"&
*a+ Complete and balance the following acid-baseeBuations)
*i+
*ii+
Answer
Solution:
%a( %i(
%ii(
!%! )eactions of Carboxylic Acids %&B $"*'(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B5:
Example !"&Exam ple !"&
*b+ raw the structural formulae for the products formedfrom the following compounds when the are reducedwith lithium tetrah dridoaluminate,
*i+
*ii+
Answer
Solution:
%b( %i(
%ii( 12C1 , C1 , C1 , C1 , 21
!%! )eactions of Carboxylic Acids %&B $"*'(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B51
Example !"&Exam ple !"&*c+ Complete the following eBuations)
*i+
*ii+
*iii+
Answer
Solution:
%c( %i(
%ii(
%iii(
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 52/84
New Way Chemistry for Hong Kong A-Level Book 3B5$
Both chlorine and ox gen atoms are electron-withdrawing gro")s2 th"s making the ac l carbon much
electron-deficient ac l carbon is a good nucleophilic site
&eactions of Acyl Chlorides &eactions of Acyl Chlorides
Chloride ion is a good lea$ing group whi#h iss"%stit"te! %y other atoms or gro")s easily
ac l chlorides are $er reacti$e
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B53
Ben=oyl #hlori!e is m"#h less rea#tive than ali)hati# a#yl#hlori!es
reduction of electron-deficienc on the ac l carbon !"e to !elo#ali=ation of ele#trons *resonance effect 8
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" +(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B5*
A#yl #hlori!es are hy!roly=e! %y water to form the parent
carbox lic acids an! hy!rogen #hlori!e
Reaction with Water
Examples:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" +(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B55
A#yl #hlori!es rea#t with al#ohols to give esters an! HCl
Reaction with Alcohols
Examples:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" +(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B5,
(c l chlorides react with phenols to gi$e esters in thepresence of base as catal st
an alkaline me!i"m #onverts )henol to a )owerf"ln"#leo)hile2 phenoxide ion
Example:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" ,(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B5
(c l chlorides react with ammonia to form amides rapidl
Reaction with Ammonia and Amines
Example:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" ,(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B5
A#yl #hlori!es rea#t ra)i!ly with 1> an! $> amines to form N -" N " N - substituted amides res)e#tively
6he rea#tion takes )la#e at room temperature an! )ro!"#esamides in high ield
6his metho! is widel used in laborator for amides s nthesis
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" ,(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B59
Chec# $oint !"!Chec# $oint !"!/xplain wh ethano l chloride must be protected fromatmospheric moisture during storage,
Answer
6his is %e#a"se ethanoyl #hlori!e rea#ts rea!ilywith water 7from atmos)heri# moist"re8 to formethanoi# a#i!.
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" 3(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B,:
A#i! anhy!ri!es undergo h drol sis to form carbox lic acids
&eactions of Acid Anhydrides &eactions of Acid Anhydrides
Reaction with Water
Example:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" 3(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B,1
A#i! anhy!ri!es rea#t with al#ohols to form esters in the )resen#e of acid catal st
Reaction with Alcohols
Example:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" *(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 62/84
New Way Chemistry for Hong Kong A-Level Book 3B,$
A#i! anhy!ri!es rea#t with ammonia an! with 1> an! $>amines in the ways similar to those of a#yl #hlori!es
Reaction with Ammonia and Amines
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" *(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 63/84
New Way Chemistry for Hong Kong A-Level Book 3B,3
Examples:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" 3(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 64/84
New Way Chemistry for Hong Kong A-Level Book 3B,*
(mides are the least reacti$e among the #ar%o&yli# a#i!
!erivatives towards nucleophilic substitution reactions
NH 1 5 " NHR 5 or NR 1 5 are strong bases an! th"spoor lea$ing groups
&eactions of Amides &eactions of Amides
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B,5
Ami!e "n!ergo acid and alkaline h drol ses to form
#ar%o&yli# a#i!s an! #ar%o&ylates res)e#tively
Acid hydrolysis:
Reaction with Water
Alkaline hydrolysis:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B,,
Ami!es are !ehy!rate! %y heating with (*<
1: to form nitriles
Dehydration
sef"l syntheti# metho! for )re)aring nitriles that are
not a$ailable b nucleophilic substitution reactions
between haloalkanes and c anide ions
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B,
Ami!es rea#t with a solution of ;r 1 in NaOH or a solution of
Cl 1 in NaOH to give amines thro"gh a rea#tion #alle! Hofmanndegradation
6he res"lte! amines have one carbon less than original amides
Hofmann Degradation
Example:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" .(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B,
Ami!es are re!"#e! %y LiAlH * in !ry ether to
give !0 amines
Reduction with Lithium Tetrahydridoaluminate
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" .(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B,9
A#i!-#ataly=e! hy!rolysis of esters is the re$erse reactionof esterification
&eactions of Esters &eactions of Esters
Acid cataly!ed Hydrolysis
Example:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" .(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B:
When esters are refl"&e! with an alkali s"#h as Na<H2 the
#orres)on!ing alcohol and sodium salt of the carbox licacid are produced
Alkali-#ataly=e! hy!rolysis are irre$ersible
Al"ali cataly!ed Hydrolysis
Example:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" /(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B1
4oa) is ma!e %y the alkaline h drol sis of fats or oils
7i.e. triesters8 to )ro!"#e sodium carbox lates 7i.e. soa)86he rea#tion is #alle! saponification
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" /(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 72/84
New Way Chemistry for Hong Kong A-Level Book 3B$
sters are re!"#e! to alcohols %y LiAlH*
Reduction with Lithium Tetrahydridoaluminate
Example:
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" /(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B3
Example !"!Exam ple !"!raw the structural formulae of the missing compounds ( to
.)*a+
*b+
*c+
Answer
Solution:
%a(
%b(
%c(
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" 0(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 74/84
New Way Chemistry for Hong Kong A-Level Book 3B*
Example !"!Exam ple !"!raw the structural formulae of the missing compounds ( to
.)*d+
*e+
*f+
Answer
Solution:
%d(
%e(
%f(
!%' )eactions of the Derivatives of Carboxylic Acids %&B $" 0(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 75/84
New Way Chemistry for Hong Kong A-Level Book 3B5
Example !"!Exam ple !"!raw the structural formulae of the missing compounds ( to
.)*g+
*h+
*i+
Answer
Solution:
%4(
%h(
%i(
!% 5ses of Carboxylic Acids and their Derivatives %&B $" '(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 76/84
New Way Chemistry for Hong Kong A-Level Book 3B,
;en2oic acid and its sodium salt "se! as foo! )reservatives
're$ent the microbial growth and spoilage
se! in oyster sa"#e2 fishsa"#e2 ket#h")2 non-al#oholi#
%everages2 fr"it F"i#es2margarine2 sala! !ressings2
Fams an! )i#kle! )ro!"#ts
As $ood )reser*ati*es As $ood )reser*ati*es
!% 5ses of Carboxylic Acids and their Derivatives %&B $" '(
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 77/84
New Way Chemistry for Hong Kong A-Level Book 3B
As &aw materials for +akin )olymers As &aw materials for +akin )olymers
N lon->"> 2 2is a
condensation pol mer
t is a )olyami!e ma!e %y a!!ing Na<H #ontaininghexanedio l dichloride an! hexane-!">-diamine to CH 3CCl 3
!% 5ses of Carboxylic Acids and their Derivatives %&B $". (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B
Advantages o Nylon-
6,6rip dr easil
Not atta#k %y inse#ts easily
Resist creasing 7no ironing reG"ire!after washing8
se! for making ro)es2 threa!2 #or!s2an! vario"s kin!s of #lothing fromsto#kings to Fa#kets
7 l 2 2 i ) l
!% 5ses of Carboxylic Acids and their Derivatives %&B $". (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 79/84
New Way Chemistry for Hong Kong A-Level Book 3B9
7er lene 2 2 is a )olyester
ma!e from acid-catal 2ed condensation pol meri2ation
of ben2ene-!" -dicarbox lic acid and ethane-!"1-diol
Terylene is used to make wash-and-wear garments
!% 5ses of Carboxylic Acids and their Derivatives %&B $". (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 80/84
New Way Chemistry for Hong Kong A-Level Book 3B:
LiG"i! esters are wi!ely "se! as sol$ents for all-purposeadhesi$es 2thinners for paints an! nail $arnish remo$ers
As %ol*ents As %ol*ents
!% 5ses of Carboxylic Acids and their Derivatives %&B $". (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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New Way Chemistry for Hong Kong A-Level Book 3B1
Jolatile esters often have characteristic sweet andfruit smells
6hey are "se! as artificial fla$ourings in food-processing industr
As $la*o"rin s As $la*o"rin s
An artificial flavouringmade of esters
!% 5ses of Carboxylic Acids and their Derivatives %&B $". (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 82/84
New Way Chemistry for Hong Kong A-Level Book 3B$
Structure of ester Characteristicfla$our
Banana
A))le
A)ri#ot
(inea))le
Some esters and their characteristic flavours
!% 5ses of Carboxylic Acids and their Derivatives %&B $". (
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
http://slidepdf.com/reader/full/a2-chemistry-carboxylic-acids-and-their-derivatives 83/84
New Way Chemistry for Hong Kong A-Level Book 3B3
Structure of ester Characteristic fla$our
+"m
/ra)e
Wintergreen
Some esters and their characteristic flavours (cont’d
7/23/2019 A2 Chemistry Carboxylic Acids and Their Derivatives
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The E D