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S  60 `P   P*    6 `   R*  H  0޽h ? ̙3380___PPT10. 0X(   $+ X X 0 P    X*  X 0T     Z*  X 6ģ `P   X*  X 6H `   Z* H X 0޽h ? ̙3380___PPT10.1 0L0 P,(    04 +AN INTRODUCTION TO THE CHEMISTRY OF ALKENEST!(2 82 f0f<f " <̙? x @ 0 0 ( <̙? x @L 0 0 ) 0,Cx m OKNOCKHARDY PUBLISHING(2 f + 0B 2008 SPECIFICATIONS>G$G   J , C "A KTRE 8  hB  s *޽h ? ̙33y___PPT10Y+D=' = @B +  0L0    (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0S   0l0Pa 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, dB   <D?     0+{0P( OKNOCKHARDY PUBLISHING(2    0X fTHE CHEMISTRY OF ALKENES2(2$f<fB  s *޽h ? ̙33y___PPT10Y+D=' = @B +f  0L0 u m ` (    08l  CONTENTS Structure of alkenes Nomenclature Isomerism Physical properties of alkenes Electrophilic addition reactions of alkenes Addition to unsymmetrical alkenes Other reactions Polymerisation Preparation of alkenes Revision check listV 202 2,p W0dB  <D)P0Q  0Pp@ 0 0dB  @ <D)PXP   0X0@ 0 0  03e .@o  0 0  63~m !@  0 0  63p]P @  0 0  63Km8 @  0 0  63> ] @  0 0  63! m3 @  0 0  63 m _@  0 0  0ʏX fTHE CHEMISTRY OF ALKENES2(2$f<f  63 e @  0 0  63 e o @  0 0  63 e @  0 0B  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 p(  f  0֏H0  \Before you start it would be helpful to& Recall the definition of a covalent bond Understand the difference between homolytic and heterolytic fission Be able to balance simple equations Be able to write out structures for hydrocarbons Recall the chemical and physical properties of alkanes H*(2 2)>y  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0X fTHE CHEMISTRY OF ALKENES2(2$f<fB  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 1(  O   0 >0 General are members of a homologous series hydrocarbons - contain only C and H general formula is CnH2n - for non-cyclic alkenes unsaturated - atoms can be added to their formula contain a C=C double bond somewhere in their structure @2' .    ) *  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  <̙? x @Y 0 0  0"> fTHE STRUCTURE OF ALKENES2(2ffB  s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 ` L(      0+>0  JGeneral are members of a homologous series hydrocarbons - contain only C and H general formula is CnH2n - for non-cyclic alkenes unsaturated - atoms can be added to their formula contain a C=C double bond somewhere in their structure Structure spacial arrangement around the C=C is planar the bond angles are 120"K@2' .    ) + '&  A dB   <D)P0Q   0Pp@ 0 0dB  @ <D)PXP   0X0@ 0 0   <̙? x @  0 0   01> fTHE STRUCTURE OF ALKENES2(2ffL   C $A) sp29g xB   s *޽h ? ̙33y___PPT10Y+D=' = @B + 0L0 //H(  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0 l> gHYBRIDISATION OF ORBITALS2(2f3{  s *d>?{  !;The electronic configuration of a carbon atom is 1s22s22p2 <13333333 < >`@F y" !   " N W 3   yE ! fB   6Df>fB   6Dok lB   <D~   N??M W #  0D>W+ C1&(2  0>_)3 F1s((2#N ;   y" fB  6Do: : fB  6Df> n fB  6DoV X lB  <Dn sV lB  <Dn: l ~  N?? T  P x  #  ~  N?? P + ~  N??+P  ~  N??P x   0>;V *  C2&(2  0\>   F2s((2  0>   F2p((28T Zo # @v X fB  6DooofB  B 6DoZo8T Zo !# v  fB " 6DooofB #B 6DoZo8T Zo $# @VXfB % 6DooofB &B 6DoZo8T Zo '# VfB ( 6DooofB )B 6DoZo8T Zo *# H .` fB + 6DooofB ,B 6DoZo8T Zo -#  . fB . 6DooofB /B 6DoZoB  s *޽h ? ̙33. 0L0 --YY0-(  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0> gHYBRIDISATION OF ORBITALS2(2f3{  s *D>?{  !;The electronic configuration of a carbon atom is 1s22s22p2 <13333333 < >`@F y" !   " N W 3   yE ! fB   6Df>fB   6Dok lB   <D~   N??M W #  0>W+ C1&(2  0>_)3 F1s((2#N ;   y" fB  6Do: : fB  6Df> n fB  6DoV X lB  <Dn sV lB  <Dn: l ~  N?? T  P x  #  ~  N?? P + ~  N??+P  ~  N??P x   0t>;V *  C2&(2  0>   F2s((2  0>   F2p((28T Zo # @v X fB  6DooofB  B 6DoZo8T Zo !# v  fB " 6DooofB #B 6DoZo8T Zo $# @VXfB % 6DooofB &B 6DoZo8T Zo '# VfB ( 6DooofB )B 6DoZo8T Zo *# H .` fB + 6DooofB ,B 6DoZo8T Zo -#  . fB . 6DooofB /B 6DoZo 0 s *z?u{  cIf you provide a bit of energy you can promote (lift) one of the s electrons into a p orbital. The configuration is now 1s22s12p3 y333333  >`@F O '  1 O  N W 3 2 O K ' fB 3 6Df>fB 4 6Dok lB 5 <D~ 6 N??M W # 7 0 zW+ C1&(2 8 0>_)3 F1s((2#N ;  9 O fB : 6Do: : fB ; 6Df> n fB < 6DoV X lB = <Dn sV lB > <Dn: l ~ ? N?? T  P x  @#  ~ A N?? P + ~ B N??+P  ~ C N??P x  D 0z;V *  C2&(2 E 0z   F2s((2 F 0Dz   F2p((28T Zo G# | . fB H 6DooofB IB 6DoZo8T Zo J# ]| u fB K 6DooofB LB 6DoZo8T Zo M# \.fB N 6DooofB OB 6DoZo8T Zo P# 46fB Q 6DooofB RB 6DoZo8T Zo S# 4fB T 6DooofB UB 6DoZo8T Zo V# z,fB W 6DooofB XB 6DoZo} Y s */z?Y #wThe process is favourable because the of arrangement of electrons; four unpaired and with less repulsion is more stable`x 3A3 3 x >`@B  s *޽h ? ̙33! 0L0   DD? (  j  B?,` dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0> #HYBRIDISATION OF ORBITALS - ALKANESD$(2f33J  C "A% orbpw Q J   C "A& orbs  l   s *&z?gm The four orbitals (an s and three p s) combine or HYBRIDISE to give four new orbitals. All four orbitals are equivalent.ny2 3  33t     (      >`@0L Zo  # +] fB   6DooofB  B 6DoZoj  B?a j  B?` j  B?` 0L Zo # ) fB  6DooofB B 6DoZo0L Zo # 3 fB  6DooofB B 6DoZo0L Zo # / fB  6DooofB B 6DoZoj  B? _ 0L Zo # *  fB  6DooofB B 6DoZoj  B?S @ X j  B?I 6 _ j   B?? , _ 0L Zo !# (  fB " 6DooofB #B 6DoZo0L Zo $# 2t  fB % 6DooofB &B 6DoZo0L Zo '# 3h  fB ( 6DooofB )B 6DoZoj * B?yfW 0L Zo +# " fB , 6DooofB -B 6DoZoj . B?X j / B?$W j 0 B?|W 0L Zo 1#  ( fB 2 6DooofB 3B 6DoZo0L Zo 4# *Ov fB 5 6DooofB 6B 6DoZo0L Zo 7# + fB 8 6DooofB 9B 6DoZovB : ND>?S6vB ; ND>?  < s *Hhz?}# 2s22p2P  3  >`@ = s *@{z?}6  2s12p3P  3  >`@ > s *bz?}.  4 x sp36  3  >`@J ? C "A% orbpw t  Q J @ C "A% orbpw h  Q N A C &A'sporbgU G N B C &A'sporbgU  N C C &A'sporbgU T N D C &A'sporbgU . B  s *޽h ? ̙33U" 0L0 !!EE!( 'r j  B?,` dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0z #HYBRIDISATION OF ORBITALS - ALKENESD$(2f33J  C "A% orbpw Q J   C "A& orbs     s *z?gS `Alternatively, only three orbitals (an s and two p s) combine or HYBRIDISE to give three new orbitals. All three orbitals are equivalent. The remaining 2p orbital is unchanged.nA 3  3(3t    )     8 >`@0L Zo  # +] fB   6DooofB  B 6DoZoj  B?a j  B?` j  B?` 0L Zo # ) fB  6DooofB B 6DoZo0L Zo # 3 fB  6DooofB B 6DoZo0L Zo # / fB  6DooofB B 6DoZoj  B? _ 0L Zo # *  fB  6DooofB B 6DoZoj  B?S @ _ j  B?I 6 _ j   B?? , _ 0L Zo !# (  fB " 6DooofB #B 6DoZo0L Zo $# 2t  fB % 6DooofB &B 6DoZo0L Zo '# 3h  fB ( 6DooofB )B 6DoZoj * B?yfW 0L Zo +# " fB , 6DooofB -B 6DoZoj . B?yX j / B?W j 0 B?|W 0L Zo 1#   fB 2 6DooofB 3B 6DoZo0L Zo 4# * fB 5 6DooofB 6B 6DoZo0L Zo 7# + fB 8 6DooofB 9B 6DoZovB : ND>?S6vB ; ND>?  < s *z?}# 2s22p2P  3  >`@ = s *z?}6  2s12p3P  3  >`@ > s *Pz?}V  3 x sp26  3  >`@J ? C "A% orbpw t  Q J @ C "A% orbpw h  Q  A s *z?}a v2p(3  >`@J B C "A% orbpU T/ N C C &A'sporbgU 7 N D C &A'sporbgU b N E C &A'sporbgU r B  s *޽h ? ̙33 0L0 A9 (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0L  C $A sp21gF  L  C $A sp22g4  L  C $A# sp31gy+   s *z?X ? 0^In ALKANES, the four sp3 orbitals repel each other into a tetrahedral arrangement. HOWEVER...l_  < 3&  > >`@   s *}?Y  C}In ALKENES, the three sp2 orbitals repel each other into a planar arrangement and the 2p orbital lies at right angles to them`~ d3&  \ >`@vB   ND>?     0xz fTHE STRUCTURE OF ALKENES2(2f3B  s *޽h ? ̙33 0L0 NF (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0L  C $A sp23g L  C $A sp24g L  C $A  sp25g R   s *(}?~Xy 8  1Covalent bonds are formed by overlap of orbitals.*213&(   >`@-   s * !}?~ 8  CAn sp2 orbital from each carbon overlaps to form a single C-C bond.DD =3 D >`@b   s *0}?| 6 \The resulting bond is called a SIGMA () bond.H/&#3$&  >`@   0&} fTHE STRUCTURE OF ALKENES2(2f3B  s *޽h ? ̙33 0L0 | (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0L  C $A! sp26gL  C $A" sp27g D  s *?}?4  The two 2p orbitals also overlap to form a second bond. This is known as a PI () bond. For maximum overlap and hence the strongest bond, the 2p orbitals are in line. This gives rise to the planar arrangement around C=C bonds.P#33[3X   < C  K >`@   0E} fTHE STRUCTURE OF ALKENES2(2f3B  s *޽h ? ̙33  0L0    4 (  .  0@X}  Jtwo sp2 orbitals overlap to form a sigma bond between the two carbon atoms:KH D&  ; dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0   0`}q~ "ORBITAL OVERLAP IN ETHENE - REVIEWD#(2fL  C $A$ sp28g = L  C $A sp24g?=n  0f} p Ftwo 2p orbitals overlap to form a pi bond between the two carbon atoms(GHF&  8 L  C $A! sp26gpZ  0Tm} P ; Ps orbitals in hydrogen overlap with the sp2 orbitals in carbon to form C-H bondsFQH* %@  "     0t}  l; 6the resulting shape is planar with bond angles of 1207H7 7 L   C $A) sp29g X  B  s *޽h ? ̙33  0L0    xF (  x" x 0H}8 Alkenes are named according to standard IUPAC rules " select the longest chain of C atoms containing the double bond; " place the ending ENE on the basic name " number the chain starting from the end nearer the double bond " use a number to indicate the lower number carbon of the C=C " as in alkanes, prefix with substituents " side chain positions are based on the number allocated to the first C of the C=C " if geometrical isomerism exists, prefix with cis or trans e.g. CH3 - CH = CH - CH2 - CH(CH3) - CH3 is called 5-methylhex-2-ene 5H@ 3   73>    Z4       d dB x <D)P0Q x 0Pp@ 0 0dB x@ <D)PXP x 0X0@ 0 0  x 0}q~ \NAMING ALKENES2(2ffB x s *޽h ? ̙33 0L0   tL(  tdB t <D)P0Q t 0Pp@ 0 0dB t@ <D)PXP t 0X0@ 0 0 t 0}q~ bISOMERISM IN ALKENES2(2ff"  t 0}~A BTwo types of isomerism found in alkenes STRUCTURAL GEOMETRICALPC($3$ C B t s *޽h ? ̙33; 0L0 0 hi(  hdB h <D)P0Q h 0Pp@ 0 0dB h@ <D)PXP h 0X0@ 0 0 h 0 }q~ mSTRUCTURAL ISOMERISM IN ALKENES2 (2ff2  h 0}T Different structures are possible due to... Different positions for the double bond pent-1-ene pent-2-ene Branching 3-methybut-1-ene,(/ 2,(&3 3  L  h C $A pent1% L  h C $A pent2f R  h C *Amethbutg ` P B h s *޽h ? ̙33 0L0 @ }( w |B  TDjJ?3R _3|B  TDjJ?//  0}s \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0   s *,}?p KIntroduction an example of stereoisomerism found in some, but not all, alkenes occurs due to the RESTRICTED ROTATION OF C=C bonds get two forms...H@ Z!  N   C &Agiso2c N   C &Agiso2t B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +I  0L0 X P p (  |B  TDjJ?3R _3|B  TDjJ?//  0}s \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0   s *t}?p KIntroduction an example of stereoisomerism found in some, but not all, alkenes occurs due to the RESTRICTED ROTATION OF C=C bonds get two forms...H@ Z!  N   C &Agiso2c N   C &Agiso2t -   s *?%  M  =CIS (Z) Groups/atoms are on the SAME SIDE of the double bondf>H3  > 4   s *?5 M  DTRANS (E) Groups/atoms are on OPPOSITE SIDES across the double bondfEH 3 E B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +" 0L0 1) (    0s \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0   s *h?0 pE/Z or CIS-TRANS0H    B!UeO QE / Z    6O  Z (zusammen) higher priority groups / atoms on the SAME side of C=C bond E (entgegen) higher priority groups / atoms on OPPOSITE sides of C=C bond  +f 'f@  H  D B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0    (& (  ( ( 0ls \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB ( <D)@0A ( 0Pp@ 0 0dB (@ <D)@X@ ( 0X0@ 0 0 ( s *&?0 pE/Z or CIS-TRANS0H   ( B6UeO QE / Z    ( 6<O  Z (zusammen) higher priority groups / atoms on the SAME side of C=C bond E (entgegen) higher priority groups / atoms on OPPOSITE sides of C=C bond  +f 'f@  H  D W  ( 0}   To determine priority, the Cahn, Ingold and Prelog convention is used. eg C2H5 > CH3 > H and I > Br > Cl > F > C > HT            3   B ( s *޽h ? ̙33y___PPT10Y+D=' }= @B +#  0L0 2 *  , (  , , 00bs \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB , <D)@0A , 0Pp@ 0 0dB ,@ <D)@X@ , 0X0@ 0 0 , s * CH3 > H and I > Br > Cl > F > C > HT            3   H  , C A-ez1  J  , C "A. ez2g1  B , s *޽h ? ̙33y___PPT10Y+D=' }= @B +? 0L0 N F $ (  $ $ 0ts \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB $ <D)@0A $ 0Pp@ 0 0dB $@ <D)@X@ $ 0X0@ 0 0 $ s *?0 pE/Z or CIS-TRANS0H   $ B@UeO QE / Z    $ 64O  Z (zusammen) higher priority groups / atoms on the SAME side of C=C bond E (entgegen) higher priority groups / atoms on OPPOSITE sides of C=C bond  +f 'f@  H  D W  $ 0X   To determine priority, the Cahn, Ingold and Prelog convention is used. eg C2H5 > CH3 > H and I > Br > Cl > F > C > HT            3   H  $ C A-ez1  J  $ C "A. ez2g1    $ B@CM,= ME   $ B ŇNuK H MZ   $ B,LJ8`62 MZ   $ B͇CP/= ME  B $ s *޽h ? ̙33y___PPT10Y+D=' }= @B +9  0L0 H@ 0(  0 0 0@؇s \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB 0 <D)@0A 0 0Pp@ 0 0dB 0@ <D)@X@ 0 0X0@ 0 0 0 s *݇?0 pE/Z or CIS-TRANS0H   0 BׇU= X CIS / TRANS     0 6|O   Should only be used when there are two H s and two non-hydrogen groups attached to each carbon. cis non-hydrogen groups / atoms on the SAME side of C=C bond trans non-hydrogen groups / atoms on OPPOSITE sides of C=C bond a'f#f&a   B 0 s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0  4(  4 4 0Ps \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB 4 <D)@0A 4 0Pp@ 0 0dB 4@ <D)@X@ 4 0X0@ 0 0 4 s *?0 pE/Z or CIS-TRANS0H   4 BU= X CIS / TRANS     4 6 O   Should only be used when there are two H s and two non-hydrogen groups attached to each carbon. cis non-hydrogen groups / atoms on the SAME side of C=C bond trans non-hydrogen groups / atoms on OPPOSITE sides of C=C bond a'f#f&a   J  4 C "A. ez2g RN S J  4 C "A ez3gk S B 4 s *޽h ? ̙33y___PPT10Y+D=' }= @B +!  0L0 0 (   (      0s \ GEOMETRICAL ISOMERISM IN ALKENES !(2!fdB   <D)@0A   0Pp@ 0 0dB  @ <D)@X@   0X0@ 0 0   s *?0 pE/Z or CIS-TRANS0H     B"U= X CIS / TRANS      6-O   Should only be used when there are two H s and two non-hydrogen groups attached to each carbon. cis non-hydrogen groups / atoms on the SAME side of C=C bond trans non-hydrogen groups / atoms on OPPOSITE sides of C=C bond a'f#f&a   J   C "A. ez2g RN S    B86 H ]cis     Bd9   Qtrans  J   C "A ez3gk S    Bl= =  ]cis     BB ]X Qtrans  B   s *޽h ? ̙33y___PPT10Y+D=' }= @B +\  0L0 k c P ( w   0Hs QGEOMETRICAL ISOMERISM (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0   s *pO? jRESTRICTED ROTATION OF C=C BONDS Single covalent bonds can easily rotate. What appears to be a different structure is not. It looks like it but, due to the way structures are written out, they are the same. j"H@!'  L   C $A  12iso`^2   6?H;q^2   6?R g {F   s *hZ?8 0  ALL THESE STRUCTURES ARE THE SAME BECAUSE C-C BONDS HAVE  FREE ROTATION,IHHf I `F b    K~B  ND3o?  B  TLD3o?b k `F b     K~B  ND3o?  B  TLD3o?b k ^2  6?Ra{P  C (Anewgiag,     0_ p  hAnimation doesn t work in old versions of Powerpoint5(25 * B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +/  0L0 > 6 ` (    0hs QGEOMETRICAL ISOMERISM (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0X   s *m? bRESTRICTED ROTATION OF C=C BONDS C=C bonds have restricted rotation so the groups on either end of the bond are  frozen in one position; it isn t easy to flip between the two.l"H@!3n  N   C &Agiso2c  N   C &Agiso2t M `F b       / ~B   ND3o?  B  TLD3o?b k {  s *w? (  !This produces two possibilities. The two structures cannot interchange easily so the atoms in the two molecules occupy different positions in space.\HR#  BF _  : Z rB  BD>?rrB B BD>?_R  C *A(newgi2ag_   0X hAnimation doesn t work in old versions of Powerpoint5(25 * B  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 pR(    0 s QGEOMETRICAL ISOMERISM (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0   s *?Q/ vHow to tell if it exists.H     6?  R 2(2(   6?H O R O2(20   6`? %  R O2(20   6ܠ?L  R 2(2(  0d? #Two different atoms/groups attachedH$H    0?G  #Two different atoms/groups attachedH$H    0`?tM !Two similar atoms/groups attachedH"H 3  0?dO = !Two similar atoms/groups attachedH"H 3  0俋?1   !Two similar atoms/groups attachedH"H 3  0\Ƌ?1 G  #Two different atoms/groups attachedH$H    0 ͋?/  #Two different atoms/groups attachedH$H    0xӋ?/ G  #Two different atoms/groups attachedH$H  L  C $A  gisosq`  0ً?>P  YGEOMETRICAL ISOMERISM(H   0? P  YGEOMETRICAL ISOMERISM(H   6?h  iOnce you get two similar atoms/groups attached to one end of a C=C, you cannot have geometrical isomerism.jH i33B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0   z (    0ts QGEOMETRICAL ISOMERISM (2fdB  <D)@0A  0Pp@ 0 0dB @ <D)@X@  0X0@ 0 0   s *?Q/ rIsomerism in butene There are 3 structural isomers of C4H8 that are alkenes*. Of these ONLY ONE exhibits geometrical isomerism.Hl@#  34&   n J   C "A  c4h8F    s *? S  U but-1-ene H      s *< ?   [2-methylpropeneH     s *X?   trans but-2-ene (E) but-2-eneNH      s *? A   cis but-2-ene (Z) but-2-eneNH    j  BԔ?E O  s *?+ " I* YOU CAN GET ALKANES WITH FORMULA C4H8 IF THE CARBON ATOMS ARE IN A RING|J@#" J B  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0    H (  H H 0 0$ Boiling point trends are similar to those shown in alkanes increases as they get more carbon atoms in their formula more atoms = greater intermolecular Van der Waals forces greater intermolecular force = more energy to separate molecules greater energy required = higher boiling point the lower members are gases at room temperature and pressure cyclohexene C6H10 is a liquid for isomers, greater branching = lower boiling point C2H4 (- 104 C) C3H6 (- 48C) ....... C6H10 (83C) Melting point general increase with molecular mass the trend is not as regular as that for boiling point. Solubility alkenes are non-polar so are immiscible (don t mix with) with water miscible with most organic solvents.@ l  D33333  33333 3333333 `   Ut3  h       ~ dB H <D)P0Q H 0Pp@ 0 0dB H@ <D)PXP H 0X0@ 0 0  H 0*q~ lPHYSICAL PROPERTIES OF ALKENES2(2ffB H s *޽h ? ̙33y___PPT10Y+D=' }= @B +H  0L0 W O  ( w dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0   0&q~ lCHEMICAL PROPERTIES OF ALKENES2(2ff   0, } | ELECTROPHILIC ADDITION MECHANISM,!  !   01|@  :The main reaction of alkenes is addition Because of the extra electron density in a C=C double bond, alkenes are attacked by species which  like electrons.8 v  R  C *Aeaintro1,< 8  049( @  These species are called electrophiles; they possess a positive or partial positive charge somewhere in their structure. Examples include... hydrogen halides concentrated H2SO4 i 3&    R  C *Aeaintro2(  B  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0  ( ACHEM\sp dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0 Oq~ lCHEMICAL PROPERTIES OF ALKENES2(2ff   0P } | ELECTROPHILIC ADDITION MECHANISM,!  ! R  C *Aeaintro3V 4  0xU*. h  )The electrophile, having some positive character, is attracted to the alkene. The electrons in the pi bond come out to form a bond to the positive end. Because hydrogen can only have two electrons in its orbital, its other bond breaks heterolytically. The H attaches to one of the carbon atoms.**Z   6    . B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0     (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0fq~ lCHEMICAL PROPERTIES OF ALKENES2(2ff  0o } | ELECTROPHILIC ADDITION MECHANISM,!  ! R  C *Aeaintro5 NP R   C *Aeaintro3V 4R   C *Aeaintro4 " 89   0p*. h  )The electrophile, having some positive character, is attracted to the alkene. The electrons in the pi bond come out to form a bond to the positive end. Because hydrogen can only have two electrons in its orbital, its other bond breaks heterolytically. The H attaches to one of the carbon atoms.**t          .    0vD  A carbocation is formed. The species that left now has a lone pair. It acts as nucleophile and attacks the carbocation using its lone pair to form a covalent bond. Overall, there is ADDITION D Z   C      K dB   <Do @ B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0  TP(  TdB T <D)P0Q T 0Pp@ 0 0dB T@ <D)PXP T 0X0@ 0 0 T 0q~ lCHEMICAL PROPERTIES OF ALKENES2(2ff  T 0Ѝ0  zReagent Hydrogen bromide... it is electrophilic as the H is slightly positive Condition Room temperature. Equation C2H4(g) + HBr(g)    > C2H5Br(l) bromoethane Mechanism vP`xF 333333333  Z$   U        T 0 } *ELECTROPHILIC ADDITION OF HYDROGEN BROMIDE,+* + L  T C $A eaddg  X B T s *޽h ? ̙33y___PPT10Y+D=' }= @B +M  0L0 \ T   (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0q~ lCHEMICAL PROPERTIES OF ALKENES2(2ff|  0X0 Reagent Hydrogen bromide... it is electrophilic as the H is slightly positive Condition Room temperature. Equation C2H4(g) + HBr(g)    > C2H5Br(l) bromoethane Mechanism Step 1 As the HBr nears the alkene, one of the carbon-carbon bonds breaks The pair of electrons attaches to the slightly positive H end of H-Br. The HBr bond breaks to form a bromide ion. A carbocation (positively charged carbon species) is formed. P`xF 333333333  3 1$   U     #     u  '   1   0Փ} *ELECTROPHILIC ADDITION OF HYDROGEN BROMIDE,+* + L   C $A eaddg  X B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0     (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0ޓq~ lCHEMICAL PROPERTIES OF ALKENES2(2ff  000R Reagent Hydrogen bromide... it is electrophilic as the H is slightly positive Condition Room temperature. Equation C2H4(g) + HBr(g)    > C2H5Br(l) bromoethane Mechanism Step 1 As the HBr nears the alkene, one of the carbon-carbon bonds breaks The pair of electrons attaches to the slightly positive H end of H-Br. The HBr bond breaks to form a bromide ion. A carbocation (positively charged carbon species) is formed. Step 2 The bromide ion behaves as a nucleophile and attacks the carbocation. Overall there has been addition of HBr across the double bond.P`xF 333333333  3 13$   U     #     u  '   U      &     0} *ELECTROPHILIC ADDITION OF HYDROGEN BROMIDE,+* + L   C $A eaddg  X B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +G  0L0  @ (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0q~ lCHEMICAL PROPERTIES OF ALKENES2(2ff  0$ >ELECTROPHILIC ADDITION OF HYDROGEN BROMIDE ANIMATED MECHANISM*?, ?   C (A+eaanimR? ,$D 0  0N  5Animation repeats continuously after every 10 seconds66f 6 B  s *޽h ? ̙33___PPT10+6D' }= @B DA' = @BA?%,( < +O%,( < +Dx' =%(%(D' =%(D' =4@BBBB%(E' =1B B`BPB1:Bhidden*3>+B#style.visibility= `B<*D' =1:Bvisible*o3>+B#style.visibility<*%(+  0L0 - %   (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  00q~ lCHEMICAL PROPERTIES OF ALKENES2(2ffP   06  Reagent Bromine. (Neat liquid or dissolved in tetrachloromethane, CCl4 ) Condition Room temperature. No catalyst or UV light required! Equation C2H4(g) + Br2(l)   > CH2BrCH2Br(l) 1,2 - dibromoethane Mechanism It is surprising that bromine should act as an electrophile as it is non-polar. SEE NEXT SLIDE FOR AN EXPLANATION OF THE BEHAVIOUR OF BROMINERKxt@ 4  63333 3333333 3R3 3 >Z0     F   c    0]3} {!ELECTROPHILIC ADDITION OF BROMINE*"! " T   C ,A br2polar2pi B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0    _ (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0lq~ lCHEMICAL PROPERTIES OF ALKENES2(2ffg  0u  It is surprising that bromine should act as an electrophile as it is non-polar. Explanation ... as a bromine molecule approaches an alkene, electrons in the pi bond of the alkene repel the electron pair in the bromine-bromine bond thus inducing a dipole.PP Z/   J  $  O   0 ~3} {!ELECTROPHILIC ADDITION OF BROMINE*"! " <   0> @x  AS A NON-POLAR BROMINE MOLECULE APPROACHES AN ALKENE, ELECTRONS IN THE PI ORBITAL OF THE ALKENE REPEL THE SHARED PAIR OF ELECTRONS IN THE Br-Br BOND  V   C .Abr2polar1gT x   PAParchment     040 W NON-POLAR    B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0 - %   (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0q~ lCHEMICAL PROPERTIES OF ALKENES2(2ffg   0D  It is surprising that bromine should act as an electrophile as it is non-polar. Explanation ... as a bromine molecule approaches an alkene, electrons in the pi bond of the alkene repel the electron pair in the bromine-bromine bond thus inducing a dipole.PP Z/   J  $  O    0`X3} {!ELECTROPHILIC ADDITION OF BROMINE*"! " @  0` @x  AS A NON-POLAR BROMINE MOLECULE APPROACHES AN ALKENE, ELECTRONS IN THE PI ORBITAL OF THE ALKENE REPEL THE SHARED PAIR OF ELECTRONS IN THE Br-Br BOND     04   cTHE ELECTRON PAIR IS NOW NEARER ONE END SO THE BROMINE MOLECULE IS POLAR AND BECOMES ELECTROPHILIC.dd d V  C .Abr2polar1gT   00 W NON-POLAR      0P ePOLAR03  B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0   j (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0q~ lCHEMICAL PROPERTIES OF ALKENES2(2ff   0, The addition of bromine dissolved in tetrachloromethane (CCl4) or water (known as bromine water) is used as a test for unsaturation. If the reddish-brown colour is removed from the bromine solution, the substance possesses a C=C bond.6< @%  @   h    0Ǘ3M 7ELECTROPHILIC ADDITION OF BROMINE TEST FOR UNSATURATION8"x7 8 N   C &A BrH2OgPy i @   0͗z x  PLACE A SOLUTION OF BROMINE IN A TEST TUBE ADD THE HYDROCARBON TO BE TESTED AND SHAKE IF THE BROWN COLOUR DISAPPEARS THEN THE HYDROCARBON IS AN ALKENE    0ӗrl   A B Cd 333    0ܗ< y P#   A B CJ33  D  08 5 |Because the bromine adds to the alkene, it no longer exists as molecular bromine and the typical red-brown colour disappears}}&   W XB  0D i B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +5  0L0 D <   ( w dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0q~ lCHEMICAL PROPERTIES OF ALKENES2(2ff   0j  Z`Reagent Concentrated sulphuric acid (85%) Conditions 0C Equation C2H4(g) + H2SO4(conc)   > C2H5OSO2OH(aq) ethyl hydrogensulphate Hydrolysis the product can be converted to ethanol by boiling with water. C2H5OSO2OH(aq) + H2O(l)   > H2SO4(aq) + C2H5OH(l) Industrial method(s) Phosphoric acid (H3PO4) and steam are used - see later Ethanol can also be made by FERMENTATION:@2>@&K@EQ@22" 3333 33333333333' A333333333333 33333  S&      0<)(I} (ELECTROPHILIC ADDITION OF SULPHURIC ACID,)( ) B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0    X(  XdB X <D)P0Q X 0Pp@ 0 0dB X@ <D)PXP X 0X0@ 0 0 X 00q~ o!ADDITION TO UNSYMMETRICAL ALKENES2"(2!ff  X 059  x2Problem " addition of HBr to propene gives two isomeric brominated compounds " HBr is unsymmetrical and can add in two ways " products are not formed to the same extent " the problem doesn't arise in ethene because it is symmetrical. Mechanism Two possibilities@f          ~  =   X 0xD3} {!ELECTROPHILIC ADDITION TO PROPENE*"! " R  X C *Apropadd1 dR  X C *Apropadd22Y B X s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 0 t(  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0U  0 A Russian scientist, Markownikoff, investigated the products of the addition of hydrogen halides to alkenes. He found that, when two products were formed, one was formed in a larger quantity. His original rule was based only on this reaction. The modern version uses carbocation stability as a criterion for predicting the products. In the electrophilic addition to alkenes the major product is formed via the more stable carbocation (carbonium ion) zN@|Tx3      @   H         0_3} &MARKOWNIKOFF S RULE*    0eq~ o!ADDITION TO UNSYMMETRICAL ALKENES2"(2!ffB  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 '   (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0H   0xqx A Russian scientist, Markownikoff, investigated the products of the addition of hydrogen halides to alkenes. He found that, when two products were formed, one was formed in a larger quantity. His original rule was based only on this reaction. The modern version uses carbocation stability as a criterion for predicting the products. In the electrophilic addition to alkenes the major product is formed via the more stable carbocation (carbonium ion) Carbocation Stability Build up of charge in one place leads to instability. If it can be spread around or neutralised in some way, stability is increased. Alkyl groups are electron releasing and can  push electrons towards the carbocations thus reducing the charge density. least stable most stable methyl < primary (1) < secondary (2) < tertiary (3)RN@|@yMx3(3      @   H                03} &MARKOWNIKOFF S RULE*     0̖q~ o!ADDITION TO UNSYMMETRICAL ALKENES2"(2!ffN   C &Acarbog& KB  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0   0G ( %E X dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0T0] In the addition to propene, path A involves a 2 carbocation, path B a 1 carbocation. As the 2 ion is more stable, the major product (i.e. 2-bromopropane) is formed this way.RWnZ]=Z        \    0H3} &MARKOWNIKOFF S RULE,     0̵q~ o!ADDITION TO UNSYMMETRICAL ALKENES2"(2!ffR   C *Apropadd1q R   C *Apropadd2F   00} NPATH A, 2  0J 01  NPATH B, 2  08Þu x5  Y MAJOR PRODUCT0(2 33  04Ǟi   kPRIMARY CARBOCATION<   0Оa  iSECONDARY CARBOCATION8    0Ԟx Y MINOR PRODUCT0(2 33B  s *޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0 P s(  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0ݞq~ o!ADDITION TO UNSYMMETRICAL ALKENES2"(2!ff  03 5ELECTROPHILIC ADDITION TO PROPENE ANIMATED MECHANISM46# 6    0XN  5Animation repeats continuously after every 10 seconds66f 6 P   C (A*PropagRO B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +!  0L0 0 ( @ (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0q~ lCHEMICAL PROPERTIES OF ALKENES2(2ff   0. DIRECT HYDRATION Reagent steam Conditions high pressure Catalyst phosphoric acid Product alcohol Equation C2H4(g) + H2O(g) C2H5OH(g) ethanol Use ethanol manufacture Comments It may be surprising that water needs such vigorous conditions to react with ethene. It is a highly polar molecule and you would expect it to be a good electrophile. However, the O-H bonds are very strong so require a great deal of energy to be broken. This necessitates the need for a catalyst.<@2<  3333 33 33333  _@  G       03} rOTHER ADDITION REACTIONS*  8 ?  7 _*@  fB   6D3olB  <BD3o{>T  # L)?fB  6D3olB  <BD3o{B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +_  0L0 nfP (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0.q~ lCHEMICAL PROPERTIES OF ALKENES2(2ff   003 nHYDROGENATION Reagent hydrogen Conditions nickel catalyst - finely divided Product alkanes Equation C2H4(g) + H2(g)    > C2H6(g) ethane Use margarine manufacture@2   3333 3333333 &W  Z    00-3} rOTHER ADDITION REACTIONS*  B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0   ` \3 (  \dB \ <D)P0Q \ 0Pp@ 0 0dB \@ <D)PXP \ 0X0@ 0 0 \ 0\q~ gPOLYMERISATION OF ALKENES2(2ff  \ 0b0 JProcess " during polymerisation, an alkene undergoes an addition reaction with itself " all the atoms in the original alkenes are used to form the polymer " long hydrocarbon chains are formedx@(S <&%     \ 0 l3} sADDITION POLYMERISATION,    \ 0@U0  the equation shows the original monomer and the repeating unit in the polymer ethene poly(ethene) MONOMER POLYMER Wn(x T9@i     ' P  \ C (AlongpolP \ C (Apolyethr (  \ 0xq( 0 cn represents a large number, 2f3B \ s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0   pL (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0臤q~ gPOLYMERISATION OF ALKENES2(2ff   0|@r bETHENE,H(3     0̏P@} }#EXAMPLES OF ADDITION POLYMERISATION*$# $ N   C &A4polsg.b&  0 gPROPENE0H(33    0 ?~ kTETRAFLUOROETHENE*@(3     0\ @  l CHLOROETHENE0 H( 33    0l|Rhr Z POLY(ETHENE) @( 3    0Rh [ POLY(PROPENE)@(3    0 R  +POLY(CHLOROETHENE) POLYVINYLCHLORIDE PVC>,@(3  3 ,   0 p :X `POLY(TETRAFLUOROETHENE) PTFE  Teflon ,1@(3  1 B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0    B ( SSSS dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0:   0 Preparation Many are prepared by a free radical process involving high pressure, high temperature and a catalyst. The catalyst is usually a substance (e.g. an organic peroxide) which readily breaks up to form radicals whichinitiate a chain reaction. Another famous type of catalyst is a Ziegler-Natta catalyst (named after the scientists who developed it). Such catalysts are based on the compound TiCl4. Properties Physical varied by changing the reaction conditions (pressure, temperature etc). Chemical have chemical properties based on the functional groups in their structure. poly(ethene) is typical; it is fairly inert as it is basically a very large alkane. This means it is resistant to chemical attack and non-biodegradable.V  F 3  3Jt   A  #   A  I    0tפ3} qADDITION POLYMERISATION*     0dܤq~ gPOLYMERISATION OF ALKENES2(2ffB  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0    ? (  dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0  0pq~ gPOLYMERISATION OF ALKENES2(2ff8   0  *Although polymers derived from alkenes are invaluable to modern society, their disposal creates widespread problems. " they are unreactive to most chemicals and bacteria (non-biodegradable) " if they are just discarded they add to the landfill problem recycling high cost of collection and re-processing burn waste saves on landfill sites and produces energy toxic fumes (HCl) can be removed from burning chlorinated polymers feedstock use the waste for the production of useful organic compounds new technology can convert waste into hydrocarbons hydrocarbons can then be turned back into polymers.J)D3" 333:3@          03} pPROBLEMS WITH POLYMERS*  B  s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0    `t (  `dB ` <D)P0Q ` 0Pp@ 0 0dB `@ <D)PXP ` 0X0@ 0 0 ` 0q~ dPREPARATION OF ALKENES2(2ffH  ` 0|  FROM HALOGENOALKANES - Elimination Reagent Alcoholic sodium (or potassium) hydroxide Conditions Reflux in alcoholic solution Product Alkene Mechanism Elimination Equation C3H7Br + NaOH(alc)   > C3H6 + H2O + NaBr FROM ALCOHOLS - Dehydration Reagent Conc. sulphuric acid or conc. phosphoric acid (H3PO4) Conditions Reflux Product Alkene Mechanism Dehydration (elimination of water) Equation C2H5OH(l)   > CH2=CH2(g) + H2O(l)@("f*    3333 3333 333f9       33333333 333t  0  %    e B ` s *޽h ? ̙33y___PPT10Y+D=' }= @B +  0L0 '    (    0D JREVISION CHECK (2f  0J ZWhat should you be able to do? (2   0@O0q  MRecall and explain the physical properties of alkenes Recall and explain the types of isomerism found in alkenes Recall and explain why alkenes undergo electrophilic addition Write balanced equations representing the reactions taking place in this section Understand why, in some addition reactions, a mixture of isomeric products is obtained Recall the importance of addition polymerisation, including examples` 2fffff$ff)ffffff+ffNf fMff?f,    0Xd   ~,CAN YOU DO ALL OF THESE? YES NO6- 2!    0 H @P 0 0   0f h @U 0 0dB   <D)P0Q  0Pp@ 0 0dB @ <D)PXP  0X0@ 0 0H  0޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0  ;(  9  0o  YYou need to go over the relevant topic(s) again Click on the button to return to the menudG(282/$f f) f  s * x  P @S 0 0dB  <D)P0Q  0Pp@ 0 0dB @ <D)PXP   0X0@ 0 0H  0޽h ? ̙33y___PPT10Y+D=' }= @B + 0L0  D(    0}xK (WELL DONE! Try some past paper questions@)(2 <fffdB  <D)P0Q  0Pp@ 0 0dB  @ <D)PXP   0X0@ 0 0H  0޽h ? ̙33y___PPT10Y+D=' }= @B +% 0L0 4,@(   X @ @ <̙? x @D 0 0 @ 0x m h. 2009 JONATHAN HOPTON & KNOCKHARDY PUBLISHING/(2/ f @ 08fM  STHE END0(2f<f @ 0( +AN INTRODUCTION TO THE CHEMISTRY OF ALKENEST!(2 82 f0f<fJ @ C "A KTRE 8  hH @ 0޽h ? ̙33y___PPT10Y+D=' }= @B +r<@$2`(b.O]PD d B8TX@y\m0% @Ooz3- 0s(6 BQ~&w hî9l؋<`,+fj{_5d?~GRB]kt-Oh+'0T hp   No Slide TitleHOPTONJONATHAN HOPTON756Microsoft PowerPoint@ *@@hNx@@V GSg  )'    """)))UUUMMMBBB999|PP3f333f3333f3ffffff3f̙3ff333f333333333f33333333f33f3ff3f3f3f3333f33̙33333f333333f3333f3ffffff3f33ff3f3f3f3fff3ffffffffff3ffff̙fff3fffff3fff333f3f3ff3ff33f̙̙3̙ff̙̙̙3f̙3f333f3333f3ffffff3f̙3f3f3f333f3333f3ffffff3f̙3f3ffffffffff!___wwwff4'A x(xKʦ 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