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Ԧ"# sL}$Ͻo>C'RD4 7fG'zzz#_ dIr!83卬xF(!bmB,wַfGexՌ"el0hP@lbkahfp&[гZO(HꯕI숂)b5z E7!#@5gK ^-C۞)=im3K+XkFǂҹ{b42z9u$t\dM_]ɊdA.E6ݓ%~NwH el&hBb Q:@'!-^Q*ȭ1k%Խq?j>`G-ȧޓV?@]ܤV,sBݡ^.K)KAE ai$[B$#3e {}Ձ4VEVN#yNTIB>_o8#}4|aHYR-#mɃE Iu'ʾ~.Y9JnR,O(, = -܂^-l09A޲LF $'%KSSi`2!,Gr q72hVK"5qAȞ|YinAA̐m ‘th3 8dA{eD&1CNVс;01L  U\C2AihѰ6l@qN{U//cUSC/#S~2tEXtOFIENDB`(K  $  ^ l s @ G N U \ e l    / 00DTimes New RomanttT/ 0DArial BlackmanttT/ 0" DArialBlackmanttT/ 00DCourier NewmanttT/ 01@ .  @n?" dd@  @@``  zU&-   #    J@aa^a^IKIGJGK>hH  F*2(((()('( '(&A ) # +$F<'F, wTn2RNO v(|RYYIB,   CY8888/001/0$  A@   !9* 2   & !      )    _% 3  %   ""    ^O;3%&'()*b$vQ\8cB b$lЙif\nWr' B b$bŘOSb$oj-p+$b$56i&% Ib$bpe# zt OSR$FE-Qڛb>"]Yb$@CCvk و _$b$N1i~~xR׻vj z0e0e    A A 8c8c     ?A)BCD|E|| f3f3f33f@fd g4KdKd< 0ppP <4BdBd@w 0t0/g4:d:dde 0p% pY<4!d!d@w 0t0/ʚ;ʚ;<4dddd@ x 0@r0___PPT10 pp2___PPT9/ 0? %O =O <Ots|uwx{y~ P4   0` ̙33` ` ff3333f` 333MMM` f` f` 3>?" dd@,|?" dd@   " @ ` n?" dd@   @@``PR    @ ` ` p>>L0 VN (    6x P  T Click to edit Master title style! !  0   RClick to edit Master text styles Second level Third level Fourth level Fifth level!     S  0p ``  X*  0 `   Z*  0ȭ `   Z*z  bA޽h @ ?Parchment ̙33 Default Design 0 zr@ ( )   0e <7   P*    0 o v 7  R*  d  c $ ?Em    0i  :xy  RClick to edit Master text styles Second level Third level Fourth level Fifth level!     S  6Xw <K   P*    6| v K  R*  H  0g彖 ? ̙3380___PPT10.3-Ri 0X(   $+ X X 0 <7   X*  X 0܍ v 7  Z*  X 6$ <K   X*  X 6 v K  Z* H X 0g彖 ? ̙3380___PPT10.3-q 0L0 &P, (     0@. 4THE CHEMISTRY OF AMINES A guide for A level students\(2 (26f<f  0 OKNOCKHARDY PUBLISHING(2fJ ( C "A KTRE: . ) <̙? x @ 0 0 * <̙? x @ 0 0 , 0(C"`>B 2008 SPECIFICATIONS>G$G   B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0     (  [  00P{ INTRODUCTION This Powerpoint show is one of several produced to help students understand selected topics at AS and A2 level Chemistry. It is based on the requirements of the AQA and OCR specifications but is suitable for other examination boards. Individual students may use the material at home for revision purposes or it may be used for classroom teaching if an interactive white board is available. Accompanying notes on this, and the full range of AS and A2 topics, are available from the KNOCKHARDY SCIENCE WEBSITE at... www.knockhardy.org.uk/sci.htm Navigation is achieved by... either clicking on the grey arrows at the foot of each page or using the left and right arrow keys on the keyboard (2 2(2 2   75,   0H BAMINES (2$fjB  BD)@0A  6Pp@ 0 0jB @ BD)@X@  6X0@ 0 0dB  <D?H H   0`  OKNOCKHARDY PUBLISHING(2B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0   `)0 5 (  jB   BD)@0A   6Pp@ 0 0jB  @ BD)@X@   6X0@ 0 0  6z  CONTENTS Prior knowledge Structure and classification Nomenclature Physical properties Basic properties Nucleophilic properties Amino acids Peptides and proteins Amides Check listr0}2 (33ff~ H  <?`@l 0 0  B? p@s 0 0  B? x@@ 0 0  B? q @G 0 0  B?  @N 0 0  B?q H@^ 0 0   B? H @U 0 0 & <?  @\ 0 0 ' 0Њ BAMINES (2$f ( <?*  @e 0 0 ) <?B @l 0 0B  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 p ph(  p^ p 0׊0P  Before you start it would be helpful to& know the functional groups found in organic chemistry know the arrangement of bonds around atoms recall and explain nucleophilic substitution reactions2*(2 2* dB p <D)@0A p 0Pp@ 0 0dB p@ <D)@X@ p 0X0@ 0 0  p 0( BAMINES (2$fB p s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 )!&2h ( w h h 0 VSTRUCTURE & CLASSIFICATION (2fdB h <D)@0A h 0Pp@ 0 0dB h@ <D)@X@ h 0X0@ 0 0V h s *<?jo ,Structure Contain the NH2 group Classification primary (1) amines secondary (2) amines tertiary (3) amines quarternary (4) ammonium salts Aliphatic methylamine, ethylamine, dimethylamine Aromatic NH2 group is attached directly to the benzene ring (phenylamine)<@2@2K 3 36f:f 3&3 >Z   ;   ?     @`N8  & hu  h N ? & hR N:D 23~B  h NDo?4B4xB h HDo?{{ h H? AH$ 2xB h HDo?{w {  h H?   AH$ 2TF  & h Nc h H+? & hR N:D 23xB h HDo?4B4xB h HDo?{{ h H(? ER( 23xB  h HDo?{w {  !h H?   AH$ 2XF  & "h }u  #h H4? & hR N:D 23xB $h HDo?4B4xB %h HDo?{{ &h H? ER( 23xB 'h HDo?{w {  (h H %?   ER( 23!8 ] ? 2hN:  -h N)?k? ER( 23@ ]  1h]  h H.?. E+( 2f *h N4?SM ~ R N RV 233~B +h NDo?u~B ,h NDo?4)4~B .h NDo?44 /h N0;?] 1 ER( 23xB 0h HDo?B h s *޽h ? ̙33y___PPT10Y+D=' }= @B +R 0L0 aY`(   ` ` 04D H NOMENCLATURE (2 fdB ` <D)@0A ` 0Pp@ 0 0dB `@ <D)@X@ ` 0X0@ 0 0 ` s *N?jJ  Nomenclature Named after the groups surrounding the nitrogen + amine C2H5NH2 ethylamine (CH3)2NH dimethylamine (CH3)3N trimethylamine C6H5NH2 phenylamine (aniline)@@ 3<    3   3  3    3 Zk           @`B ` s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0    _ ( `   00܍ G PREPARATION (2 fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *?.0  `Amines can be prepared from halogenoalkanes Reagent Excess, alcoholic ammonia (WHY USE EXCESS?) Conditions Reflux in excess, alcoholic solution under pressure Product Amine (or its salt due to a reaction with the acid produced) Nucleophile Ammonia (NH3) Equation C2H5Br + NH3 (alc)   > C2H5NH2 + HBr ( or C2H5NH3+Br ) ,H@&@,33f' 3 f$3= 3  3ffff fffffffffffffffft     )      @`F d   ^2   Bf?S"`?32   Bf?S"`?BdB  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0  -(    0( G PREPARATION (2 fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *L ;?.0 Amines can be prepared from halogenoalkanes Reagent Excess, alcoholic ammonia (WHY USE EXCESS?) Conditions Reflux in excess, alcoholic solution under pressure Product Amine (or its salt due to a reaction with the acid produced) Nucleophile Ammonia (NH3) Equation C2H5Br + NH3 (alc)   > C2H5NH2 + HBr ( or C2H5NH3+Br ) WHY USE EXCESS AMMONIA? Ammonia attacks halogenoalkanes because it has a lone pair and is a nucleophile. The amine produced also has a lone pair C2H5NH2 so can also attack a halogenoalkane; this leads to the formation of substituted amines. Using excess ammonia ensures that all the halogenoalkane molecules react with the ammonia before having the chance to react with any amines produced.,H@&@Hx,3' 4=  3ffff ffffffffffffffff3z   Zf3     )    E  %   G  a  ^  @`8 d   ^2  Bf?S"`?32   Bf?S"`?BdF d   < F _ 2   B?S"`?32   B?S"`?BdB  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 l?(   l l 0њ OPHYSICAL PROPERTIES (2fdB l <D)@0A l 0Pp@ 0 0dB l@ <D)@X@ l 0X0@ 0 0( l s *;?j]  DThe LONE PAIR on the nitrogen atom in 1, 2 and 3 amines makes them ... LEWIS BASES - they can be lone pair donors BRNSTED-LOWRY BASES - they can be proton acceptors RNH2 + H+   > RNH3+ NUCLEOPHILES - provide a lone pair to attack an electron deficient centreD@#N@ 3= f%f"ff fffff f@ #  @`B l s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0 /' ( p0p0   0@ OPHYSICAL PROPERTIES (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *(;?j{ Boiling point Boiling points increase with molecular mass Amines have higher boiling points than corresponding alkanes because of their intermolecular hydrogen bonding Quarternary ammonium salts are ionic and exist as salts Solubility Lower mass compounds are soluble in water due to hydrogen bonding with the solvent. Solubility decreases as the molecules get heavier. Soluble in organic solvents.z 3=3B3D 3@y  ;     @`L  C $A pep5g J L   C $A  pep6gPB  s *޽h ? ̙33y___PPT10Y+D=' }= @B +/  0L0 >6`(    0H!; LBASIC PROPERTIES (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *@;?.  fBases The lone pair on the nitrogen atom makes amines basic; RNH2 + H+   > RNH3+ a proton acceptor Strength depends on the availability of the lone pair and its ability to pick up protons " the greater the electron density on the N, the better it can pick up protons " this is affected by the groups attached to the nitrogenFx39ff ffff f3f3f n  @`B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0 P(    0D; LBASIC PROPERTIES (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0.  s *k;?.    Bases The lone pair on the nitrogen atom makes amines basic; RNH2 + H+   > RNH3+ a proton acceptor Strength depends on the availability of the lone pair and its ability to pick up protons " the greater the electron density on the N, the better it can pick up protons " this is affected by the groups attached to the nitrogen electron withdrawing substituents (benzene rings) decrease basicity as the electron density on N is lowered and the lone pair is less effectivePx39ff ffff f3f3f@     O  @`TL ] # h t xB B HDԔ?]IxB  HDԔ?I]   Hd;?' !  C6H5 N:~ 2ffff pB  HDo?  pB  HDo? h   H6;?c ^7  AH$ 2pB  HDo?]   Hx;?1^  AH$ 2B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +0 0L0 ?7$p (  p p 0; LBASIC PROPERTIES (2fdB p <D)@0A p 0Pp@ 0 0dB p@ <D)@X@ p 0X0@ 0 0 p s *س;?. F .Bases The lone pair on the nitrogen atom makes amines basic; RNH2 + H+   > RNH3+ a proton acceptor Strength depends on the availability of the lone pair and its ability to pick up protons " the greater the electron density on the N, the better it can pick up protons " this is affected by the groups attached to the nitrogen electron withdrawing substituents (benzene rings) decrease basicity as the electron density on N is lowered and the lone pair is less effective electron releasing substituents (CH3 groups) increase basicity as the electron density is increased and the lone pair is more effectivex*39ff ffff f3f3f#33h3t     h     L  @` p NL;? 9   CH3 N:X 233 vB p NDo?i i vB p NDo? " p NT;?vF AH$ 2vB p NDo?   p N;? vF  AH$ 2NF ] p h t xB pB HDԔ?]IxB p HDԔ?I]TL ] pA# ' E xB pB HD3Ԕ?]IxB p HD3Ԕ?I]  p H@;?' !  C6H5 N:~ 2ffff pB p HDo?  pB p HDo? h  p H|;?c ^7  AH$ 2pB  p HDo?]  !p HX;?1^  AH$ 2B p s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0    t ( # t t 0 LBASIC PROPERTIES (2fdB t <D)@0A t 0Pp@ 0 0dB t@ <D)@X@ t 0X0@ 0 0 t s *4u?.0 VNMeasurement the strength of a weak base is depicted by its pKb value the smaller the pKb the stronger the base the pKa value can also be used; it is worked out by applying pKa + pKb = 14 the smaller the pKb, the larger the pKa. Compound Formula pKb Comments ammonia NH3 4.76 methylamine CH3NH2 3.36 methyl group is electron releasing phenylamine C6H5NH2 9.38 electrons delocalised into the ring strongest base methylamine > ammonia > phenylamine weakest base smallest pKb largest pKbv@@@P}w@ 31 333 ;3333 3    3   "3   #33' 33 3D;    "  ;         !  r   l   !      @`pB t HDjJ?PpB  t HDjJ?j Pj B t s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 /(    0"u CHEMICAL REACTIONS - WEAK BASESD (2f 3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *u?.0  Water Amines which dissolve in water produce weak alkaline solutions CH3NH2(g) + H2O(l) CH3NH3+(aq) + OH(aq) Acids Amines react with acids to produce salts. C6H5NH2(l) + HCl(aq)   > C6H5NH3+Cl(aq) phenylammonium chloride This reaction allows one to dissolve an amine in water as its salt. Addition of aqueous sodium hydroxide liberates the free base from its salt C6H5NH3+Cl(aq) + NaOH(aq)   > C6H5NH2(l) + NaCl(aq) + H2O(l)3Affff fffffffff3+ffffffffffffffF3Nfffffff"fffffffff  K           @`F ?  % 8N    fB   6D3olB   <BD3o{>T   # L)?fB   6D3olB  <BD3o{B  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0   |( w | | 0u !CHEMICAL REACTIONS - NUCLEOPHILICD"(2f 3fdB | <D)@0A | 0Pp@ 0 0dB |@ <D)@X@ | 0X0@ 0 0o | s *(vu?j Due to their lone pair, amines react as nucleophiles Reagent Product Mechanism haloalkanes substituted amines nucleophilic substitution acyl chlorides N-substituted amides addition-eliminationz5H@7@@537f}t(   =        7  @`pB | HDjJ?pB  | HDjJ?,,B | s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0 W O ( w dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0uq~ gNUCLEOPHILIC SUBSTITUTION2(2ff  0u0i ^~HALOALKANES Amines are also nucleophiles (lone pair on N) and can attack halogenoalkanes to produce a 2 amine. This too is a nucleophile and can react further producing a 3 amine and, eventually an ionic quarternary ammonium salt. C2H5NH2 + C2H5Br   > HBr + (C2H5)2NH diethylamine, 2 amine  H@PFS@ ew333333333333333333   !  '   E   0      B  s *޽h ? ̙33;  0L0   pi (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0uq~ gNUCLEOPHILIC SUBSTITUTION2(2ff:  0(w0g  *HALOALKANES Amines are also nucleophiles (lone pair on N) and can attack halogenoalkanes to produce a 2 amine. This too is a nucleophile and can react further producing a 3 amine and, eventually an ionic quarternary ammonium salt. C2H5NH2 + C2H5Br   > HBr + (C2H5)2NH diethylamine, 2 amine (C2H5)2NH + C2H5Br   > HBr + (C2H5)3N triethylamine, 3 amine  H@PF@ eD33333333333333333333333333 33333333333  3   !  '   E   0     -      B  s *޽h ? ̙33 0L0 E= ( w dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0wq~ gNUCLEOPHILIC SUBSTITUTION2(2ff  0 w0e  L HALOALKANES Amines are also nucleophiles (lone pair on N) and can attack halogenoalkanes to produce a 2 amine. This too is a nucleophile and can react further producing a 3 amine and, eventually an ionic quarternary ammonium salt. C2H5NH2 + C2H5Br   > HBr + (C2H5)2NH diethylamine, 2 amine (C2H5)2NH + C2H5Br   > HBr + (C2H5)3N triethylamine, 3 amine (C2H5)3N + C2H5Br   > (C2H5)4N+ Br tetraethylammonium bromide a quaternary (4) salt " H@PF@ -3333333333333333333333333 33333333333  3333333 3333 333333333!3   !  '   E   0     -     I  ' B  s *޽h ? ̙33 0L0 M( w dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0bwq~ gNUCLEOPHILIC SUBSTITUTION2(2ff  0pzw0c BHALOALKANES Amines are also nucleophiles (lone pair on N) and can attack halogenoalkanes to produce a 2 amine. This too is a nucleophile and can react further producing a 3 amine and, eventually an ionic quarternary ammonium salt. C2H5NH2 + C2H5Br   > HBr + (C2H5)2NH diethylamine, 2 amine (C2H5)2NH + C2H5Br   > HBr + (C2H5)3N triethylamine, 3 amine (C2H5)3N + C2H5Br   > (C2H5)4N+ Br tetraethylammonium bromide a quaternary (4) salt Uses Quarternary ammonium salts with long chain alkyl groups are used as cationic surfactants in fabric softening e.g. [CH3(CH2)17]2N+(CH3)2 Cl. H@PF@ 333333333333333333333333 33333333333  3333333 3333 333333333!3F33       *   !  '   E   0     -     I  -      B  s *޽h ? ̙33 0L0  !( w   0,w G AMINO ACIDS (2 fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0V  s *lw?.~  Structure Amino acids contain 2 functional groups amine NH2 carboxyl COOH They all have a similar structure - the identity of R1 and R2 vary@ 3'  ff 3<     @`F     q N    Hw?3 S  H2N C COOHb 2  3   Hw?  T  OH 0(2    Hw? L  OH 0(2 xB  HDԔ? . xB  HDԔ? xB  HDԔ? Q xB  HDԔ?3  F    q s   Hlw?3 S  H2N C COOHb 2  3  H\y?  OCH30(2   H$y? L  OH 0(2 xB  HDԔ? . xB  HDԔ? xB  HDԔ? Q xB  HDԔ?3  F    9  H y?3 S  H2N C COOHb 2  3  Hxy? T  NR20(2   Hy?  Q R1 0(2 xB  HDԔ? . xB  HDԔ? xB   HDԔ? Q xB ! HDԔ?3  B  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 0!h(    0,"y >AMINO ACIDS  OPTICAL ISOMERISM2 (2f3dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *7y?j  b>Amino acids can exist as optical isomers If they have different R1 and R2 groups Optical isomers exist when a molecule Contains an asymmetric carbon atom Asymmetric carbon atoms have four different atoms or groups attached Two isomers are formed - one rotates plane polarised light to the left, one rotates it to the right Glycine doesn t exhibit optical isomerism as there are two H attached to the C atomFE<Fe-TA  ;f&L  M  @`.F    Y*   H9y?3 S  H2N C COOH~ 2 f3   H,.y?  OCH30(2    HUy? L  OH 0(2 xB   HDԔ? . xB   HDԔ? xB  HDԔ? Q xB  HDԔ?3  .F     *  HYy?3 S  H2N C COOH~ 2 f3  Hgy?  T  OH 0(2   Hmy? L  OH 0(2 xB  HDԔ? . xB  HDԔ? xB  HDԔ? Q xB  HDԔ?3     s *ry?jA GLYCINE 2-aminoethanoic acid(   @`B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +/  0L0 > 6 @ (    0Xy yAMINO ACIDS - ZWITTERIONSD(2f 3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0L  s *y?j Zwitterion " a dipolar ion " has a plus and a minus charge in its structure " amino acids exist as zwitterions " give increased inter-molecular forces " melting and boiling points are higher@ 33 3343&3+3&    @`38  *Rf V   Nxy? R H3N+ C COOh 2   !!  Ny?fFf NR20(2   Nty?^*J NR10(2 ~B  NDԔ?SnS~B  NDԔ?KSS~B  NDԔ?2~B  NDԔ?fB  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0   P (  dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0.  s *ty?j  " amino acids possess acidic and basic properties " this is due to the two functional groups " COOH gives acidic properties " NH2 gives basic properties " they form salts when treated with acids or alkalis.@33c335   @`F    <    Hy?3 S  H2N C COOHb 2  3   Hy? T  NR20(2    Hy? L  NR10(2 xB   HDԔ? . xB   HDԔ? xB  HDԔ? Q xB  HDԔ?3    0Dy "AMINO ACIDS - ACID-BASE PROPERTIESD#(2f3fB  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0 * " ` (    0Hy "AMINO ACIDS - ACID-BASE PROPERTIESD#(2f3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0v  s *a?j  0Basic properties: with H+ HOOCCH2NH2 + H+   > HOOCCH2NH3+ with HCl HOOCCH2NH2 + HCl   > HOOCCH2NH3+ Cl Acidic properties: with OH HOOCCH2NH2 + OH   > OOCCH2NH2 + H2O with NaOH HOOCCH2NH2 + NaOH   > Na+ OOCCH2NH2 + H2O$@o@3 fffffffffff ffffffffff3 ffffffffffffffffffffffN      \    "  @`B  s *޽h ? ̙33y___PPT10Y+D=' }= @B += 0L0 LDp (    0\a  PEPTIDES - FORMATION & STRUCTURED!(2 f3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *a?j  Amino acids can join together to form peptides via an amide or peptide link 2 amino acids joined dipeptide 3 amino acids joined tripeptide many amino acids joined polypeptide nLHz@63 l@l      -  @`L  C $A pep1g cL   C $A pep2g  Ha?x IaL k a dipeptide  "   B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +J  0L0 Y Q   (    0py uPEPTIDES - HYDROLYSISD(2 f 3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0^  s *wa?j Peptides are broken down into their constituent amino acids by hydrolysis " attack takes place at the slightly positive C of the C=O " the C-N bond is broken " hydrolysis with water is very slow " hydrolysis in alkaline/acid conditions is quicker " hydrolysis in acid/alkaline conditions (e.g. NaOH) will produce salts with HCl NH2 becomes NH3+Cl H+ NH2 becomes NH3+ NaOH COOH becomes COO Na+ OH COOH becomes COOJH@P@J3 ;&5\        ( %Z7  #  E  A  @`L   C $A pep3g&puB  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 ]ps(    0sa uPEPTIDES - HYDROLYSISD(2 f 3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 01  s *y?j KPeptides are broken down into their constituent amino acids by hydrolysis FJH@J3 L  @`.8 3=o #M   NPa?3 dH2N C CO: 2     N@a?Oo OCH30(2    Nia?83S OH 0(2 ~B  NDԔ?\a\~B  NDԔ?&\\~B  NDԔ?;~B  NDԔ?o  Nįa?  I NH C CO  2   Na?O o OH 0(2   Na?3 S OH 0(2 ~B  NDԔ?A\\~B  NDԔ? \. \~B  NDԔ?* ;* ~B  NDԔ?* * o  Ha?@ = KNH C COOH  2xB  HDԔ? YJ YxB  HDԔ?YYxB  HDԔ? 8 xB   HDԔ?  l ! H`a? @` OCH30(2  " H`a? Gg OCH30(2  ] Ba?VC UWhich amino acids are formed?(2B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +% 0L0 $$$9:#( 0e   0Da uPEPTIDES - HYDROLYSISD(2 f 3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 01  s *a?j KPeptides are broken down into their constituent amino acids by hydrolysis FJH@J3 L  @` F 3=o  M   Hpy?3 dH2N C CO: 2     Ha?Oo OCH30(2    HLa?83S OH 0(2 xB   HDԔ?\a\xB   HDԔ?&\\xB  HDԔ?;xB  HDԔ?o  Ha?  I NH C CO  2   Hl{?O o OH 0(2   H0{?3 S OH 0(2 xB  HDԔ?A\\xB  HDԔ? \. \xB  HDԔ?* ;* xB  HDԔ?* * o  Hp{?@ = KNH C COOH  2xB  HDԔ? YJ YxB  HDԔ?YYxB  HDԔ? 8 xB  HDԔ?  l  H{? @` OCH30(2   H{? Gg OCH30(2 F - q6   1F  H\ {? 6 OCH30(2    H${?O   OH 0(2 xB ! HDԔ?# x# xB " HDԔ?=# # xB # HDԔ?  xB $ HDԔ? 6  % H8+{?- q  fH2N C COOH: 2 F A > &  A> ' HT2{?s  > OH 0(2  ( H\7{?k  "  OH 0(2 xB ) HDԔ? + + xB * HDԔ?Y + + xB + HDԔ? xB , HDԔ? >  - H={?A   fH2N C COOH: 2 F  A6 .  6xB / HDԔ?( Y( xB 0 HDԔ?( ( xB 1 HDԔ?  xB 2 HDԔ? ;  3 HE{?) /  OCH30(2  4 HdK{?) 6 OCH30(2  5 HR{? A  fH2N C COOH: 2  6 HY{?m   E+((2 3 7 HH]{?m 7A  E+((2 3vB 8 NDԔ? vB 9 NDԔ?' ' B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +x 0L0 N(   F N |%  R  He{?N| r  dH2N C CO: 2     Hk{?; % OCH30(2  ! Hr{?w   OH 0(2 xB " HDԔ?   xB # HDԔ?e  xB $ HDԔ?  xB % HDԔ?| %  & Hx{? |  I NH C CO  2  ' H{?  : % OH 0(2  ( Hȇ{? 2  OH 0(2 xB ) HDԔ?    xB * HDԔ?  m  xB + HDԔ?i i xB , HDԔ?i | i %  - H{? y |  KNH C COOH  2xB . HDԔ?   xB / HDԔ?N  xB 0 HDԔ?  xB 1 HDԔ?y "  2 H{?i h  ?H"(2 3 Hh{?Y * OCH30(2   0L{ uPEPTIDES - HYDROLYSISD(2 f 3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 01  s *\{?j KPeptides are broken down into their constituent amino acids by hydrolysis FJH@J3 L  @` N B {?VC UWhich amino acids are formed?(2B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0 $12(   F N |%  R  Hl{?N| r  dH2N C CO: 2    H{?; % OCH30(2   H{?w   OH 0(2 xB  HDԔ?   xB  HDԔ?e  xB  HDԔ?  xB   HDԔ?| %    H{? |  I NH C CO  2    H8{?  : % OH 0(2    H@{? 2  OH 0(2 xB   HDԔ?    xB  HDԔ?  m  xB  HDԔ?i i xB  HDԔ?i | i %   H {? y |  KNH C COOH  2xB  HDԔ?   xB  HDԔ?N  xB  HDԔ?  xB  HDԔ?y "   H{?i h  ?H"(2  H {?Y * OCH30(2   0{ uPEPTIDES - HYDROLYSISD(2 f 3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 01  s *}?j KPeptides are broken down into their constituent amino acids by hydrolysis FJH@J3 L  @`F - q6   Y F  Hh{? 6 OCH30(2    H }?O   OH 0(2 xB ! HDԔ?# x# xB " HDԔ?=# # xB # HDԔ?  xB $ HDԔ? 6  % H@}?- q  fH2N C COOH: 2 F A > &  > ' H4}?s  > OH 0(2  ( Hp }?k  "  OH 0(2 xB ) HDԔ? + + xB * HDԔ?Y + + xB + HDԔ? xB , HDԔ? >  - H('}?A   fH2N C COOH: 2  . H/}?h >  G2 x((2 3 / H3}?p  E+((2 3vB 0 NDԔ? vB 1 NDԔ?' ' B  s *޽h ? ̙33y___PPT10Y+D=' }= @B += 0L0 LD( 3r3f   0d*} DPROTEINS (2 fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *:}?j ( " are polypeptides with high molecular masses " chains can be lined up with each other " the C=O and N-H bonds are polar due to a difference in electronegativity " hydrogen bonding exists between chains dotted lines ---------- represent hydrogen bonding @.)K' 3&  e  @`L  C $A pep4gf,B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0     (    0D} BAMIDES (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0&  s *}?j Structure derivatives of carboxylic acids amide group is -CONH2 Nomenclature White crystalline solids named from the corresponding acid (remove oic acid, add amide) CH3CONH2 ethanamide (acetamide) C2H5CONHC6H5 N - phenyl propanamide - the N tells you the substituent is on the nitrogen Nylons are examples of polyamides Preparation Acyl chloride + ammonia CH3COCl + NH3   > CH3CONH2 + HCl ethanoyl chloride ethanamide@P2%@PPoPP&@PF$@3@+PP 3;  3a      D% 3ffff fffff           "   P  C           @`N   C &A amideg:N@B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0   H ( =Ė   0 }} |AMIDES - CHEMICAL PROPERTIESD(2 f3fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *?j  Hydrolysis general reaction CH3CONH2 + H2O   > CH3COOH + NH3 acidic soln. CH3CONH2 + H2O + HCl   > CH3COOH + NH4Cl alkaline soln. CH3CONH2 + NaOH   > CH3COONa + NH3 Identification Warming an amide with dilute sodium hydroxide solution and testing for the evolution of ammonia using moist red litmus paper is used as a simple test for amides. Reduction Reduced to primary amines: CH3CONH2 + 4[H]   > CH3CH2NH2 + H2O@`@ 3ffff ffffffffff fffffffffffffff3 3ffffffffffffft\  '  *    9  @`B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +, 0L0 ;30@(   X @ @ 0} THE CHEMISTRY OF AMINES THE END\(2 (26f<fJ @ C "A KTRE: . @ <̙? x @ 0 0 @ <̙? x @ 0 0 @ 0d} z. 2009 JONATHAN HOPTON & KNOCKHARDY PUBLISHING0/(2&f(fH @ 0޽h ? ̙33y___PPT10Y+D=' }= @B +r@-2#l(4)O3=Ks0meR3w0G({ u~p20H\%wH ՝32jߖ٫v4= -Oh+'0T hp   No Slide TitleHOPTONJONATHAN HOPTON955Microsoft PowerPoint@@-@@hNx@kR8GSg  )'    """)))UUUMMMBBB999|PP3f333f3333f3ffffff3f̙3ff333f333333333f33333333f33f3ff3f3f3f3333f33̙33333f333333f3333f3ffffff3f33ff3f3f3f3fff3ffffffffff3ffff̙fff3fffff3fff333f3f3ff3ff33f̙̙3̙ff̙̙̙3f̙3f333f3333f3ffffff3f̙3f3f3f333f3333f3ffffff3f̙3f3ffffffffff!___www4'A x(xKʦ 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