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" )         _%  > !)-+./ 0 J23456789:;Lb$ $L?ΐU|Hb$݇f Hb$WZdxaW]Wxs#b$ !_sofw4$b$4`K( 5: Eb$T _ewOR$FE-Qڛb>"cUb$GY)P\ft!^"[b$ϟu.+mg!C~b$ Nʁ~$3 b$肟YS۟"*Uͥb$'E=0Ɯt)b$;K*)S74)b$fz)_F1U7m ]^b$fYlb$qbeD[ +b$Xԇރ8KZ%79$b$d\R 6pb$ +`ЖXa.b$3ĸKN<*2b$nR&+ ]/G?$b$٦#8+%g } z0e0e    A A 8c8c     ?A)BCD|E|| !f33f33f@3d g4KdKdX 0pp@ <4BdBd@w 0t / g4:d:d 0p% pY<4!d!d@w 0t /ʚ;ʚ;<4dddd@ x 0@r0___PPT10 pp2___PPT9/ 0? %O =xO <O_`j\kaRhilS~TbmUVcYdenfgZoWwxstvyu[zpqr^X{|} P4   0` ̙33` ` ff3333f` 333MMM` f` f` 3>?" dd@,|?" dd@   " @ ` n?" dd@   @@``PR    @ ` ` p>>L0 VN (    6lԒ P  T Click to edit Master title style! !  0Lג   RClick to edit Master text styles Second level Third level Fourth level Fifth level!     S  0ݒ ``  X*  0 `   Z*  0 `   Z*z  bA޽h @ ?Parchment ̙33 Default Design 0 zr@ ( )   0 <7   P*    0  v 7  R*  d  c $ ?Em    0  :xy  RClick to edit Master text styles Second level Third level Fourth level Fifth level!     S  6p <K   P*    6h v K  R*  H  0g彖 ? ̙3380___PPT10.3-Ri 0X(   $+ X X 0{ <7   X*  X 0~ v 7  Z*  X 6ԃ <K   X*  X 6X v K  Z* H X 0g彖 ? ̙3380___PPT10.3-q 0L0 P+ G(    0I CTHE CHEMISTRY OF ALDEHYDES AND KETONES A guide for A level students\(2(2&6f<f  0R OKNOCKHARDY PUBLISHING(2fJ ( C "A KTRE` ; H  + 0V"`>B u2008 SPECIFICATIONS2(2$   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,   0 OALDEHYDES & KETONES (2$fjB  BD)@0A  6Pp@ 0 0jB @ BD)@X@  6X0@ 0 0dB  <D?H H   0`  OKNOCKHARDY PUBLISHING(2B  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0   p)0 I (  jB   BD)@0A   6Pp@ 0 0jB  @ BD)@X@   6X0@ 0 0  6Ȗ  CONTENTS Prior knowledge Bonding in carbonyl compounds Structural differences Nomenclature Preparation Identification Oxidation Nucleophilic addition Reduction 2,4-dinitrophenylhydraziner0}2 (33ff 3  <?a8d@l 0 0  B?a h@ 0 0  B?n x@ 0 0  B?` @ 0 0  B? a @ 0 0  B?i9 H@^ 0 0   B? ah @ 0 0 & <? n@ @ 0 0 ' 0lٖ OALDEHYDES & KETONES (2$f ( <?O` @1 0 0 ) <?. IP @* 0 0B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0  pY(  pB p 0(  Before you start it would be helpful to& know the functional groups found in organic chemistry know the arrangement of bonds around carbon atoms recall and explain the polarity of covalent bonds 2*(2 2*dB p <D)@0A p 0Pp@ 0 0dB p@ <D)@X@ p 0X0@ 0 0  p 04 OALDEHYDES & KETONES (2$fB p s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0  ( Ow@   00} XCARBONYL COMPOUNDS - BONDING (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0Q  s *?j OBonding the carbon is sp2 hybridised and three sigma (s) bonds are planar bP@3 0 P  @`R   C *A COorbs4gCp   B@"}?X4e  aPLANAR WITH BOND ANGLES OF 120& (2B  s *޽h ? ̙33y___PPT10Y+D=' = @B +- 0L0 <4  (      0LO} XCARBONYL COMPOUNDS - BONDING (2fdB   <D)@0A   0Pp@ 0 0dB  @ <D)@X@   0X0@ 0 0   s *W}?j  VBonding the carbon is sp2 hybridised and three sigma (s) bonds are planar the unhybridised 2p orbital of carbon is at 90 to these ^@3 5:&V   7  @`R   C *A COorbs5gj    B[}?X4e  iPLANAR WITH BOND ANGLES OF 120. (2   Bi}?!  K P ORBITAL& (2 B   s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0  <6( kk < < 0Pp} XCARBONYL COMPOUNDS - BONDING (2fdB < <D)@0A < 0Pp@ 0 0dB <@ <D)@X@ < 0X0@ 0 0 < s *u}?jD  Bonding the carbon is sp2 hybridised and three sigma (s) bonds are planar the unhybridised 2p orbital of carbon is at 90 to these it overlaps with a 2p orbital of oxygen to form a pi (p) bond z@3 s7&V   {  @`R < C *ACOorbs1gkG   < B`{}?X4e  ePLANAR WITH BOND ANGLES OF 120* (2  < Bh}?!  S P ORBITAL. (2 B < s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0  (    0} XCARBONYL COMPOUNDS - BONDING (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *}?jD  Bonding the carbon is sp2 hybridised and three sigma (s) bonds are planar the unhybridised 2p orbital of carbon is at 90 to these it overlaps with a 2p orbital of oxygen to form a pi (p) bond z@3 s7&V   {  @`R  C *ACOorbs1gkG vB   ND)?   B}?X4e  ePLANAR WITH BOND ANGLES OF 120* (2  BL}?!  S P ORBITAL. (2   BP}?` <  QORBITAL OVERLAP&(2B  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0   @ (  @ @ 0} XCARBONYL COMPOUNDS - BONDING (2fdB @ <D)@0A @ 0Pp@ 0 0dB @@ <D)@X@ @ 0X0@ 0 0 @ s *`}?jD  Bonding the carbon is sp2 hybridised and three sigma (s) bonds are planar the unhybridised 2p orbital of carbon is at 90 to these it overlaps with a 2p orbital of oxygen to form a pi (p) bond z@3 s7&V   {  @`R @ C *ACOorbs1gkG R  @ C *ACOorbs2g G vB  @ ND)?   @ B}?X4e  ePLANAR WITH BOND ANGLES OF 120* (2  @ B}?!  S P ORBITAL. (2   @ Bh}?` <  QORBITAL OVERLAP&(2 @ B}? 0f  K NEW ORBITAL$ 2 pB @ HDo?pB @@ HDo? e B @ s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0   + ( 8   0} XCARBONYL COMPOUNDS - BONDING (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0C  s *?jD  Bonding the carbon is sp2 hybridised and three sigma (s) bonds are planar the unhybridised 2p orbital of carbon is at 90 to these it overlaps with a 2p orbital of oxygen to form a pi (p) bond as oxygen is more electronegative than carbon the bond is polarn@3 Bf&V     @`R  C *ACOorbs1gkG R   C *ACOorbs2g G R   C *ACOorbs3g `d vB   ND)?   B?X4e  ePLANAR WITH BOND ANGLES OF 120* (2  B?!  S P ORBITAL. (2   B?` <  YORBITAL OVERLAP.(2  B}? 0f  S NEW ORBITAL, 2 pB  HDo?pB @ HDo? e B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 (0 ( w   0" ZCARBONYL COMPOUNDS - STRUCTURE (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *`;?j  (Structure carbonyl groups consists of a carbon-oxygen double bond the bond is polar due to the difference in electronegativity Difference ALDEHYDES - at least one H attached to the carbonyl group O@ 3: 33 3 f-&x  P  @`R  C *ACOorbs3gJ8  l /g ! @ {  /   {  /    H-? T /t  CC = O"(2xB   HDԔ?{  xB   HDԔ?{ -    HH:? G g CH&(23  HX? l  OCH30(2  8  P JK 4 'T {  /  #  J  H0S? T /t  CC = O"(2xB  HDԔ?{  xB  HDԔ?{ -   NU? + K CH&(23  N^? P p  ?H"(2B  s *޽h ? ̙33y___PPT10Y+D=' = @B +} 0L0 $$8"(   8 8 0hV ZCARBONYL COMPOUNDS - STRUCTURE (2fdB 8 <D)@0A 8 0Pp@ 0 0dB 8@ <D)@X@ 8 0X0@ 0 0 8 s *,?jJ  Structure carbonyl groups consists of a carbon-oxygen double bond the bond is polar due to the difference in electronegativity Difference ALDEHYDES - at least one H attached to the carbonyl group KETONES - two carbons attached to the carbonyl group(@ 3: 33 3 f- f*&x    @`R 8 C *ACOorbs3gJF  l /g  8 ! !N {  /   8 {  /   8 Ho? T /t  CC = O"(2xB  8 HDԔ?{  xB  8 HDԔ?{ -  8 H(u? G g CH&(23 8 Hz? l  OCH30(2 F  P JK 8 4 'T {  /  8#  J 8 HȒ? T /t  CC = O"(2xB 8 HDԔ?{  xB 8 HDԔ?{ -  8 HT? + K CH&(23 8 HМ? P p  ?H"(2+F  g |f 8 v O u'T {  /  8#  |  8 Hd? T /t  CC = O"(2xB 8 HDԔ?{  xB 8 HDԔ?{ -  8 H? g   OCH30(2  8 H$?*F f OCH30(2 @F   8 v u'T {  /  8# 5 -  8 H? T /t  CC = O"(2xB !8 HDԔ?{  xB "8 HDԔ?{ -  #8 B?   jC2H5J(2   $8 Hl`? h OCH30(2 B 8 s *޽h ? ̙33y___PPT10Y+D=' = @B +% 0L0 %$=^4P|$( < f 4 4 0ƅ YCARBONYL COMPOUNDS - FORMULAE (2fdB 4 <D)@0A 4 0Pp@ 0 0dB 4@ <D)@X@ 4 0X0@ 0 0b 4 s *?j PMolecular C3H6O Structural C2H5CHO CH3COCH3 Displayed SkeletalrQ 3   3  f   3 Q  @`4F  l /g  4  !N {  /   4 {  /   4 Hޅ? T /t  CC = O"(2xB  4 HDԔ?{  xB  4 HDԔ?{ -  4 HpӅ? G g CH&(23 4 HL? l  jC2H5J(2  +F  g |f 4  'T {  /  4#  |  4 H? T /t  CC = O"(2xB 4 HDԔ?{  xB 4 HDԔ?{ -  4 Ht? g   OCH30(2  4 H ?*F f OCH30(2 8 w> b  84  |-  *4 N?w  QH C C C H  2xB ,4 HDԔ?aCCxB -4 HDԔ?CR CxB .4 HDԔ? C CxB /4 HDԔ?x C C~B 04 NDԔ?T>T~B 14 NDԔ?TTB~B 24 NDԔ? > ~B 34 NDԔ?  B~B 44 NDԔ? > ~B 54 NDԔ? >  64 H$?> ^ G H O H 2  74 H<?B b  c H H: 2 A8 k   J42 k J  :4 N%?kf  QH C C C O  2~B ;4 NDԔ?U~B <4 NDԔ?F~B =4 NDԔ?~B >4 NDԔ?l  B ?4 TDԔ?HHzB @4 TDԔ?H^HB A4 TDԔ?  zB C4 TDԔ?z E4 N2?  G H H H 2  G4 H7?-  wH HT 2 ~B H4 NDԔ?^xB I4 HDԔ?l  8 ]  U4M M4 N,?  ?O"(2~B N4 NDԔ?ixB R4B HDԔ?eA xB S4 HDԔ?=]xB T4 HDԔ?%8 z } ^4:V} W4 NH?  ?O"(2~B X4 NDԔ? }2 ~B Y4B NDԔ?z ( xB \4 HDԔ?  xB ]4 HDԔ? 4 4B 4 s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0  =Dc(  D D 0xN ]!CARBONYL COMPOUNDS - NOMENCLATURE "(2"fdB D <D)@0A D 0Pp@ 0 0dB D@ <D)@X@ D 0X0@ 0 0> D s *H?j  Aldehydes C2H5CHO propanal Ketones CH3COCH3 propanone CH3CH2COCH3 butanone CH3COCH2CH2CH3 pentan-2-one CH3CH2COCH2CH3 pentan-3-one C6H5COCH3 phenylethanonep 3   33f  3   3     3      3    33           m    @`B D s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 0R( Ow@   0\ ZCARBONYL COMPOUNDS - FORMATION (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 00  s *j?j  ALDEHYDES Oxidation of primary (1) alcohols RCH2OH + [O]   > RCHO + H2O beware of further oxidation RCHO + [O]   > RCOOH Reduction of carboxylic acids RCOOH + [H]   > RCHO + H2O  H@HH@H@ 3"ff!fff3ff!"ffff3   @`B  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0 (    0pp ZCARBONYL COMPOUNDS - FORMATION (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0r  s *?j  vALDEHYDES Oxidation of primary (1) alcohols RCH2OH + [O]   > RCHO + H2O beware of further oxidation RCHO + [O]   > RCOOH Reduction of carboxylic acids RCOOH + [H]   > RCHO + H2O KETONES Oxidation of secondary (2) alcohols RCHOHR + [O]   > RCOR + H2O \ H@HH@H@HQ@ 3"ff!fff3ff!"ffff3$&fff  <  @`B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 @ T( w   0X  _#CARBONYL COMPOUNDS - IDENTIFICATION $(2$fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *ч?j  IMethod 1 strong peak around 1400-1600 cm-1 in the infra red spectrum Method 2 formation of an orange precipitate with 2,4-dinitrophenylhydrazine Although these methods identify a carbonyl group, they cannot tell the difference between an aldehyde or a ketone. To narrow it down you must do a second test.J@3  3Bf@    /  @`J   C "A  1r3gK B  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0 %  P ( 6666   0 _#CARBONYL COMPOUNDS - IDENTIFICATION $(2$fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *B?j08  :Differentiation to distinguish aldehydes from ketones, use a mild oxidising agent Tollen s Reagent ammoniacal silver nitrate mild oxidising agent which will oxidise aldehydes but not ketones contains the diammine silver(I) ion - [Ag(NH3)2 ]+ the silver(I) ion is reduced to silver Ag+(aq) + e   > Ag(s) the test is known as THE SILVER MIRROR TEST  @3-3f333A%ffffff'fff3!            =        N    3  @`B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 `H(  H H 0/ _#CARBONYL COMPOUNDS - IDENTIFICATION $(2$fdB H <D)@0A H 0Pp@ 0 0dB H@ <D)@X@ H 0X0@ 0 0 H s *p?j0X , Differentiation to distinguish aldehydes from ketones, use a mild oxidising agent Tollen s Reagent ammoniacal silver nitrate mild oxidising agent which will oxidise aldehydes but not ketones contains the diammine silver(I) ion - [Ag(NH3)2 ]+ the silver(I) ion is reduced to silver Ag+(aq) + e   > Ag(s) the test is known as THE SILVER MIRROR TEST Fehling s Solution contains a copper(II) complex ion giving a blue solution on warming, it will oxidise aliphatic (but not aromatic) aldehydes the copper(II) is reduced to copper(I) a red precipitate of copper(I) oxide, Cu2O, is formed The silver mirror test is the better alternative as it works with all aldehydes Ketones do not react with Tollen s Reagent or Fehling s SolutionF|@H3-3fA%'+ 33 3m"3"3  OBf!            =        N    3                    @`B H s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0 >( w   0x},1 d(CARBONYL COMPOUNDS - CHEMICAL PROPERTIES )(2)fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *?j0  OXIDATION " provides a way of differentiating between aldehydes and ketones " mild oxidising agents are best " aldehydes are easier to oxidise " powerful oxidising agents oxidise ketones to a mixture of carboxylic acids ALDEHYDES easily oxidised to acids RCHO(l) + [O]   > RCOOH(l) CH3CHO(l) + [O]   > CH3COOH(l) N HU@ 3A #K 3(ffffft9     (   ?    @`B  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0    (    0,1 d(CARBONYL COMPOUNDS - CHEMICAL PROPERTIES )(2)fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *H?j0 (OXIDATION " provides a way of differentiating between aldehydes and ketones " mild oxidising agents are best " aldehydes are easier to oxidise " powerful oxidising agents oxidise ketones to a mixture of carboxylic acids ALDEHYDES easily oxidised to acids RCHO(l) + [O]   > RCOOH(l) CH3CHO(l) + [O]   > CH3COOH(l) KETONES oxidised under vigorous conditions to acids with fewer carbons C2H5COCH2CH3(l) + 3 [O]   > C2H5COOH(l) + CH3COOH(l) H@ 3A #K 3(fffff3>ffffffffffffffft9     (   ?  (  @`B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 p!( w   040P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *X?j  tPMechanism occurs with both aldehydes and ketones involves addition to the C=O double bond unlike alkenes, they are attacked by nucleophiles attack is at the positive carbon centre due to the difference in electronegativities alkenes are non-polar and are attacked by electrophiles undergoing electrophilic additionBQ 3F     W   I  /         @`  N??| w!V  ;C=C(2   N??| V  E ELECTROPHILES(2  N??| owV  ?ALKENES(2  <ֈ?V ow0 A CARBONYLS (2   N ??| ! V  A NON-POLAR (2   Nt$??V w!0 ;C=O(2  N(??V ! 0 =POLAR(2  N.??V 0 D NUCLEOPHILES (2   NL0??| sV  @ADDITION (2   N4??V s0 @ADDITION (2   N,8?? w!r  <Bond(2  N=?? r  IAttacking species(2  NpA?? owr  =Group(2   NE?? ! r  @Polarity (2  ! NI?? sr  >Result(2B  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0     ( X     0N0P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB   <D)@0A   0Pp@ 0 0dB  @ <D)@X@   0X0@ 0 0   s *{?j 0Reagent hydrogen cyanide - HCN (in the presence of KCN) Conditions reflux in alkaline solution Nucleophile cyanide ion CN Product(s) hydroxynitrile (cyanohydrin) Equation CH3CHO + HCN   > CH3CH(OH)CN 2-hydroxypropanenitrile Notes HCN is a weak acid and has difficulty dissociating into ions HCN H+ + CN the reaction is catalysed by alkali which helps produce more of the nucleophilic CN@30 3 3 33fffff3<fWftb             @`F ?    A o B 8N    fB   6DfjJlB   <BDfjJ{>T   # L)?fB   6DfjJlB   <BDfjJ{B   s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0  S(    0Ta0P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0   s *f?j  Mechanism Nucleophilic addition Step 1 CN acts as a nucleophile and attacks the slightly positive C One of the C=O bonds breaks; a pair of electrons goes onto the O @ 3 ff@    )   j  @`P  C (A COopt1gS+   H$k? z BSTEP 1 (2fB  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0   $(  $ $ 0(0P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB $ <D)@0A $ 0Pp@ 0 0dB $@ <D)@X@ $ 0X0@ 0 0 $ s *0?j  ;Mechanism Nucleophilic addition Step 1 CN acts as a nucleophile and attacks the slightly positive C One of the C=O bonds breaks; a pair of electrons goes onto the O Step 2 A pair of electrons is used to form a bond with H+ Overall, there has been addition of HCN@ 3 8f3f3*f3@    )     @`P $ C (A COopt1gS+  $ H? Uz BSTEP 2 (2f3  $ H? z BSTEP 1 (2B $ s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0  (( S ( ( 04ɋ0P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB ( <D)@0A ( 0Pp@ 0 0dB (@ <D)@X@ ( 0X0@ 0 0 ( s *x?j  MMechanism Nucleophilic addition Step 1 CN acts as a nucleophile and attacks the slightly positive C One of the C=O bonds breaks; a pair of electrons goes onto the O Step 2 A pair of electrons is used to form a bond with H+ Overall, there has been addition of HCN@ 3 f8f3f3*f3@    )     @`P ( C (A COopt1gS+  ( H$ڋ? Uz BSTEP 2 (2f3  ( Hҋ? z BSTEP 1 (2fB ( s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0  L(  L L 00P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB L <D)@0A L 0Pp@ 0 0dB L@ <D)@X@ L 0X0@ 0 0 L s *8?j  MMechanism Nucleophilic addition Step 1 CN acts as a nucleophile and attacks the slightly positive C One of the C=O bonds breaks; a pair of electrons goes onto the O Step 2 A pair of electrons is used to form a bond with H+ Overall, there has been addition of HCN@ 3 f8f3f3*f3@    )     @` L H?iz BSTEP 2 (2f3  L H?% z BSTEP 1 (2fP  L C (Anuadd5g0B L s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 ,l( H $ , , 00P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB , <D)@0A , 0Pp@ 0 0dB ,@ <D)@X@ , 0X0@ 0 0 , s *(?j ANIMATED MECHANISM*H3   @`Z , C 2Anucaddanim2xO B , s *޽h ? ̙33y___PPT10Y+D=' = @B +r 0L0 y 0(  0 0 0x$0P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB 0 <D)@0A 0 0Pp@ 0 0dB 0@ <D)@X@ 0 0X0@ 0 0] 0 s *@?"Z ]Watch out for the possibility of optical isomerism in hydroxynitriles CN attacks from aboveFFH@F3&6    @`P 0 C (A COopt1gfaP  0 C (A COopt2g Za  0 s *J?0   zCN attacks from below@3   @`B 0 s *޽h ? ̙33y___PPT10Y+D=' = @B +k 0L0 zr (    0M0P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0^  s *S?" ^Watch out for the possibility of optical isomerism in hydroxynitriles CN attacks from aboveFFH@F3&6    @`   s *`W? z+  zCN attacks from below@3   @`L   C $A nuad2m Z`L   C $A nuad1Z=B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 P(  P P 0,m0P f*CARBONYL COMPOUNDS - NUCLEOPHILIC ADDITION +(2+fdB P <D)@0A P 0Pp@ 0 0dB P@ <D)@X@ P 0X0@ 0 0 P s *r?"8 ;ANIMATED MECHANISM TO SHOW HOW DIFFERENT ISOMERS ARE FORMED<H<3 <  @`Z P C 2Anucaddanim2xO B P s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 ,( w dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *?j mReagent sodium tetrahydridoborate(III) (sodium borohydride), NaBH4 Conditions aqueous or alcoholic solution Mechanism Nucleophilic addition (also reduction as it is addition of H) Nucleophile H (hydride ion) @39  3 3A 3t      >   5     @`  0$m )CARBONYL COMPOUNDS - REDUCTION WITH NaBH4X*(2$f333B  s *޽h ? ̙33y___PPT10Y+D=' = @B +\  0L0 k c P| (  |dB | <D)@0A | 0Pp@ 0 0dB |@ <D)@X@ | 0X0@ 0 0 | s *Hڎ?jD  BReagent sodium tetrahydridoborate(III) (sodium borohydride), NaBH4 Conditions aqueous or alcoholic solution Mechanism Nucleophilic addition (also reduction as it is addition of H) Nucleophile H (hydride ion) Product(s) Alcohols Aldehydes are REDUCED to primary (1) alcohols. Ketones are REDUCED to secondary (2) alcohols. Equation(s) CH3CHO + 2[H]   > CH3CH2OH CH3COCH3 + 2[H]   > CH3CHOHCH3 Notes The water provides a proton @,@%@39  3 3A 3 3r 3fffffffffffffff3      >   5   )   -    @` | 0m )CARBONYL COMPOUNDS - REDUCTION WITH NaBH4X*(2$f333B | s *޽h ? ̙33y___PPT10Y+D=' = @B +L 0L0 [ S @x (  xdB x <D)@0A x 0Pp@ 0 0dB x@ <D)@X@ x 0X0@ 0 0 x s *?j 2 Reagent sodium tetrahydridoborate(III) (sodium borohydride), NaBH4 Conditions aqueous or alcoholic solution Mechanism Nucleophilic addition (also reduction as it is addition of H) Nucleophile H (hydride ion) Product(s) Alcohols Aldehydes are REDUCED to primary (1) alcohols. Ketones are REDUCED to secondary (2) alcohols. Equation(s) CH3CHO + 2[H]   > CH3CH2OH CH3COCH3 + 2[H]   > CH3CHOHCH3 Notes The water provides a proton Question NaBH4 doesn t reduce C=C bonds. WHY? CH2 = CHCHO + 2[H]    > CH2 = CHCH2OH@,@%@0@@@9  L}3 3 ff%fffff      >   5   )   -     @` x 0m )CARBONYL COMPOUNDS - REDUCTION WITH NaBH4X*(2$f333B x s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0  d(  ddB d <D)@0A d 0Pp@ 0 0dB d@ <D)@X@ d 0X0@ 0 0 d s *ˎ?j: lReagent sodium tetrahydridoborate(III) (sodium borohydride), NaBH4 Conditions aqueous or alcoholic solution Mechanism Nucleophilic addition (also reduction as it is addition of H) Nucleophile H (hydride ion)@39  3 3A 3t      >   5     @` d 0lm )CARBONYL COMPOUNDS - REDUCTION WITH NaBH4X*(2$f333^  d C 6ANShydridestep1r B d s *޽h ? ̙33y___PPT10Y+D=' = @B +,  0L0 ; 3  h(  hdB h <D)@0A h 0Pp@ 0 0dB h@ <D)@X@ h 0X0@ 0 0 h s *xp?j: lReagent sodium tetrahydridoborate(III) (sodium borohydride), NaBH4 Conditions aqueous or alcoholic solution Mechanism Nucleophilic addition (also reduction as it is addition of H) Nucleophile H (hydride ion)@39  3 3A 3t      >   5     @` h 0dm )CARBONYL COMPOUNDS - REDUCTION WITH NaBH4X*(2$f333T h C ,ANShydridemK   h hA?ParchmentS" ?    h hA?ParchmentS" ?r    h <?n 2 U ZWater is added(2  B h s *޽h ? ̙33y___PPT10Y+D=' = @B +]  0L0 l d  p (  pdB p <D)@0A p 0Pp@ 0 0dB p@ <D)@X@ p 0X0@ 0 0 p s *l?j: lReagent sodium tetrahydridoborate(III) (sodium borohydride), NaBH4 Conditions aqueous or alcoholic solution Mechanism Nucleophilic addition (also reduction as it is addition of H) Nucleophile H (hydride ion)@39  3 3A 3t      >   5     @` p 0lm )CARBONYL COMPOUNDS - REDUCTION WITH NaBH4X*(2$f333T p C ,ANShydridemK   p <?n 2 U ZWater is added(2    p <? @  _Primary alcohol (2f3    p <h? x  fAldehyde (2 f3  B p s *޽h ? ̙33y___PPT10Y+D=' = @B +$  0L0 3+0 t(  tdB t <D)@0A t 0Pp@ 0 0dB t@ <D)@X@ t 0X0@ 0 0 t s *?j: lReagent sodium tetrahydridoborate(III) (sodium borohydride), NaBH4 Conditions aqueous or alcoholic solution Mechanism Nucleophilic addition (also reduction as it is addition of H) Nucleophile H (hydride ion)@39  3 3A 3t      >   5     @` t 0pm )CARBONYL COMPOUNDS - REDUCTION WITH NaBH4X*(2$f333j  t B? H  t <l%? x  ^ANIMATED MECHANISM(2  R  t C *ANaBH4ag1 ~B t s *޽h ? ̙33y___PPT10Y+D=' = @B +z/ 0L0 ..O`.(  `2 Y` Bఖo"` > dB ` <D)@0A ` 0Pp@ 0 0dB `@ <D)@X@ ` 0X0@ 0 0 ` 0 m %THE TETRAHYDRIDOBORATE(III) ION BH4Z&(2"f3332 2` Bxo"`&}R > 2 4` Z?f3jJ?A=2 5` Z?f3jJ?'^2 6` Z?f3jJ?9 7` <RC IB   ^2 8` 6oc #2 9` Z?f!jJ?)t :` <4Ɩ43  GH  ^2 ;` 6o[ 2 <` Z?f!jJ?!   =` <˖T S  GH  d2 >` <o[2 ?`  `?f!jJ?!e @` BtЖ%$ GH  ^2 A` 6o>  2 B` Z?f!jJ?w R  C` <\Ֆ lk  UH$   ^2 I` 6oL 2 J` Z?f!jJ? K` <Hۖq GH  ^2 L` 6oKQ 2 M` Z?f!jJ? N` <l GH  ^2 O` 6o<H2 P` Z?f!jJ?+ Q` <x GH   U` 0}  q9each atom needs one electron to complete its outer shell :(2: V` 0\aNU Y!atom has three electrons to share"(2" W` 0 0L  t<boron shares all 3 electrons to form 3 single covalent bonds=(2= Z` <0i IB   vB \` ND>?A A2 ]` B\o"` (z > ^2 a` 6o 2 b` Z?f!jJ? c` <]('} GH  ^2 d` 6o7  2 e` Z?f!jJ?   f` <   GH  ^2 g` 6ot s4 2 h` Z?f!jJ?   i` <    GH   j` 0p]V  d,The hydride ion forms a dative covalent bond-(2- k` <XU *  IB   2 l` Z?f!jJ?7 U pB m` HDԔ? 9 k 2 E` Z?f3jJ?K|2 ^` Z?f3jJ?7 p 2 t` Bo"` z > ^2 w` 6o [2 x` Z?f!jJ?k y` <]} GH  ^2 z` 6o7 ` 2 {` Z?f!jJ? `  |` <   GH  ^2 }` 6ot K4 2 ~` Z?f!jJ? l  ` <H&   GH   ` <4!U   IB   ^2 ` 6o/ h(  ` <<.}   GH  2 ` Z?f3jJ?7 H 2 ` Z?f!jJ?7 u 2 ` Z?f!jJ?w x vB `@ NDf>?  pB ` HDԔ?  pB ` HD3Ԕ?2 G` Z?f3jJ?&,2 F` Z?f3jJ?#2 _` Z?f3jJ?  2 `` Z?f3jJ? 2 u` Z?f3jJ? c 2 v` Z?f3jJ?{B ` s *޽h ? ̙33y___PPT10Y+D=' = @B +E  0L0 T L  (    09m z,CARBONYL COMPOUNDS - REDUCTION WITH HYDROGEN2-(2$f 3dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *C?j  N<Reagent hydrogen Conditions catalyst - nickel or platinum Reaction type Hydrogenation, reduction Product(s) Alcohols Aldehydes are REDUCED to primary (1) alcohols. Ketones are REDUCED to secondary (2) alcohols. Equation(s) CH3CHO + H2   > CH3CH2OH CH3COCH3 + H2   > CH3CHOHCH3 Note Hydrogen also reduces C=C bonds CH2 = CHCHO + 2H2   > CH3CH2CH2OH@3  3 33 3n 3ff fffffffffffff ffff3 fffffffffff@   +    @`B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 *"(    0Ym ZCARBONYL COMPOUNDS - REDUCTION (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *He?j,  DIntroduction Functional groups containing multiple bonds can be reduced C=C is reduced to CH-CH C=O is reduced to CH-OH CN is reduced to CH-NH2 Hydrogen H" H2 H+ (electrophile) H (nucleophile) H@S@P@(@PZ 3v 3  #@        @`B  s *޽h ? ̙33y___PPT10Y+D=' = @B +O  0L0 ^ V T (  T T 0im ZCARBONYL COMPOUNDS - REDUCTION (2fdB T <D)@0A T 0Pp@ 0 0dB T@ <D)@X@ T 0X0@ 0 0 T s *T?j6 x&Introduction Functional groups containing multiple bonds can be reduced C=C is reduced to CH-CH C=O is reduced to CH-OH CN is reduced to CH-NH2 Hydrogen H" H2 H+ (electrophile) H (nucleophile) Reactions Hydrogen reduces C=C and C=O bonds CH2 = CHCHO + 4[H]   > CH3CH2CH2OH Hydride ion H reduces C=O bonds CH2 = CHCHO + 2[H]   > CH2=CHCH2OH Explanation C=O is polar so is attacked by the nucleophilic H C=C is non-polar so is not attacked by the nucleophilic HH@S@P@(@PZ/@ @ 3v 3  # 33 fff3f3fffffff%fff3fffff 3f31 3+t         2     @`B T s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0  \Q(  \ \ 0 m ZCARBONYL COMPOUNDS - REDUCTION (2fdB \ <D)@0A \ 0Pp@ 0 0dB \@ <D)@X@ \ 0X0@ 0 0 \ s *ؙ?j~ :Example What are the products when Compound X is reduced?8;@32 ;  @`P \ C (AC=Ored1hwP B  \ ZDԔ?0 B  \ ZDԔ?o 0  \ s *Й?\ 7 @  NaBH4FH333   @` \ s *̙?  H2FH333   @` \ s *<ș?0 l COMPOUND X H    @`B \ s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0   X (  X X 0`$m ZCARBONYL COMPOUNDS - REDUCTION (2fdB X <D)@0A X 0Pp@ 0 0dB X@ <D)@X@ X 0X0@ 0 0 X s *X*?j~ :Example What are the products when Compound X is reduced?8;@32 ;  @`P X C (AC=Ored1hwP P  X C (AC=Ored2 #p P  X C (AC=Ored3  #  X s *9? K AmC=O is polar so is attacked by the nucleophilic H C=C is non-polar so is not attacked by the nucleophilic HZ3@;P0f8f@#   /     @`B  X ZDԔ?0 B  X ZDԔ?o 0  X s *=?\ 7 @  NaBH4BH33   @` X s *K?  H2BH33   @` X s *d/?0 l COMPOUND X H    @`B X s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0 0 (    0V0P r2,4-DINITROPHENYLHYDRAZINE (2f dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *@?jU 8Structure Use reacts with carbonyl compounds (aldehydes and ketones) used as a simple test for aldehydes and ketones makes orange crystalline derivatives - 2,4-dinitrophenylhydrazones derivatives have sharp, well-defined melting points also used to characterise (identify) carbonyl compounds. Identification / characterisation A simple way of characterising a compound (finding out what it is) is to measure the melting point of a solid or the boiling point of a liquid.8@H 33!3ft7          l  @`R   C *A24dnph2gk sU   0w  C6H3(NO2)2NHNH2(2      B  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0   @ ( x   0ؕ0P A+2,4-DINITROPHENYLHYDRAZINE C6H3(NO2)2NHNH2,(2fffffffffff+ dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0   s *?j0P\  The following structural isomers have similar boiling points because of similar van der Waals forces and dipole-dipole interactions. They would be impossible to identify with any precision using boiling point determination. L@ 3@T      @`8  <T  zl Z  C *A24dnph1g     H?T   ;CHO(2   HP?l ;CHO(2   H?< ;CHO(2   H?   XCl (23  Hx?th XCl (23  Hě?T  XCl (23B  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0   2 (    08˛0P A+2,4-DINITROPHENYLHYDRAZINE C6H3(NO2)2NHNH2,(2fffffffffff+ dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0  s *?j0P  .2The following structural isomers have similar boiling points because of similar van der Waals forces and dipole-dipole interactions. They would be impossible to identify with any precision using boiling point determination. Boiling point 213C 214C 214C @I f37f33@T      @`F  <T   zl Z   C *A24dnph1g     H?T   ;CHO(2   H؛?l ;CHO(2   H,?< ;CHO(2   HH?   XCl (23  H<?th XCl (23  H?T  XCl (23B  s *޽h ? ̙33y___PPT10Y+D=' = @B +2 0L0 A9p (    0 0P A+2,4-DINITROPHENYLHYDRAZINE C6H3(NO2)2NHNH2,(2fffffffffff+ dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0-  s *h?j0P 3The following structural isomers have similar boiling points because of similar van der Waals forces and dipole-dipole interactions. They would be impossible to identify with any precision using boiling point determination. Boiling point 213C 214C 214C Melting point of 2,4-dnph derivative 209C 248C 265C By forming the 2,4-dinitrophenylhydrazone derivative and taking its melting point, it will be easier to identify the unknown original carbonyl compound.&@@H f37f33f3f 37f33!@T      @`F  <T   zl Z   C *A24dnph1g     Hp$?T   ;CHO(2   H'?l ;CHO(2   H*?< ;CHO(2   H@?   XCl (23  HC?th XCl (23  HG?T  XCl (23B  s *޽h ? ̙33y___PPT10Y+D=' = @B +2 0L0 A9` (    0|F0P A+2,4-DINITROPHENYLHYDRAZINE C6H3(NO2)2NHNH2,(2fffffffffff+ dB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0-  s *8^?j0P 3The following structural isomers have similar boiling points because of similar van der Waals forces and dipole-dipole interactions. They would be impossible to identify with any precision using boiling point determination. Boiling point 213C 214C 214C Melting point of 2,4-dnph derivative 209C 248C 265C By forming the 2,4-dinitrophenylhydrazone derivative and taking its melting point, it will be easier to identify the unknown original carbonyl compound.&@@H f37f33f3f 37f33!@T      @`F  <T   zl Z   C *A24dnph1g     H@h?T   ;CHO(2   HXk?l ;CHO(2   Hpn?< ;CHO(2   H\?   XCl (23  H?th XCl (23  Hx?T  XCl (23B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 @H(   X @ @ <̙?8x@= 0 0 @ 0)  .THE CHEMISTRY OF ALDEHYDES AND KETONES THE ENDn(2(2&6f<f  @ 0 . 2009 JONATHAN HOPTON & KNOCKHARDY PUBLISHING@/(2f&f-fJ @ C "A KTRE` ; H H @ 0޽h ? ̙33y___PPT10Y+D=' = @B +r@1'-OT6t@4NR(@2ISD%l^ ?T[`$EZcu{<.dv7~ l)3޺2wrV#d]s/&HOh+'0T hp   No Slide TitleHOPTONJONATHAN HOPTON913Microsoft PowerPoint@@@hNx@]GSg  )'    """)))UUUMMMBBB999|PP3f333f3333f3ffffff3f̙3ff333f333333333f33333333f33f3ff3f3f3f3333f33̙33333f333333f3333f3ffffff3f33ff3f3f3f3fff3ffffffffff3ffff̙fff3fffff3fff333f3f3ff3ff33f̙̙3̙ff̙̙̙3f̙3f333f3333f3ffffff3f̙3f3f3f333f3333f3ffffff3f̙3f3ffffffffff!___www4'A x(xKʦ 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