ALLENES Allenes are compounds having the general structure abC=C=Cde or abC=C=Cab Allenes will be optical active provided a ¥ b and d¥e. Mirror a b ' b a If a = b then it contains a vertical NZ 7 NZ plane of symmetry and will not be C i ¢ optically active. 1 a 1 Cc \ 7 if ¢ c Cc OS a om b ‘ i ' Cc, 4 7“ Not superimposable d Enantiomers optically inactive 7 i Mirror images Chiral axis “ = But NOT superimposable b ia Enantiomers “oP hil An allene contains a chiral Cc axis passing through the Tl double bonds. ¢ bacl H ‘ozco=c’ H cl Clan, ye Qo: b W“OGDAN,, orbital drawing central carbon is sp hybridized sp? hybridized sp* hybridized i eo ined HAHN, the x bonds formed as a = of the overlap of the p orbitals must be at right angles to each other a e A PS, not only are the two x bonds perpendicular, but the two CHCI groups are tooCumulene with even number of double bonds exhibits optical isomerism. mirror by ger eG eHe b ab 7 \ JC=C=C=C=CY a a Not superimposable Enantiomers Cumulene with odd number of double bonds exhibits geometrical isomerism. by /p ay /p aC =C=C. Je =G=C=C, 7 cis- a b trans- a Specification of the absolute configuration of allenes. viewed trom A end a counter-clockwiseAllenes-related compounds If one of the double bonds in an allene is replaced by a ring, the general shape of the allene molecule is retained. H conn Ho,6 H 2! t 2 Yo” No’ Me H : H Me Not superimposable Enantiomers s Q. Specify the absolute configuration of the following. cl H- CO2H HO2C. OH NZ 2 ic \” Mesc,. t c t c 5 Ti ud g c, CMe cl