03 Unsaturated Compounds Worksheet Key

03 Unsaturated Compounds Worksheet Key - CHEMISTRY 225...

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Unformatted text preview: CHEMISTRY 225 UNSATURATED COMPOUNDS WORKSHEET a. ( / 11) Bombykol, the sex attractant of the male silkworm moth Bombyx mori was named Molecule of the Week for the week of April 5, 2004 at the chemistrycrg website. A jagged line formula for bombykol is shown below. )“fiz Liv 32R“ - . N ,1 fl .1 Ag ,1 m! kiwi/REX \./" V“ x/K w/N OH g—__,__........\_.___,.__. Hv ' bombykot i—>H2’ catalyst WW 0 (3) Complete the hydrogenation reaction of bombykoi (assume excess hydrogen). 0 (6) Directly on the structure of bombykol: -Write in all vinylic hydrogens. Label these as H,.—. - Draw arrows to all covalent bonds about which there is free rotation. -Circle the double bond with the E- configuration. 0 (2) Write a jagged-line formula for a geometric isomer of bombykol. | E MAAAWOH bombykol sterecisomer b. (#14) 0 (2) Iert-Butyicthylene served as a reactant in a recent study of rhodium catalyzed additions to double bonds [Org Lett. 2004, 6, 1687]. Write a structure for tert-butylethylene. o (2) 1,5-Hexadiyne (C6H3) served as the starting material in the synthesis of an unsaturated carboxylic acid [Tetrahedron Lett, 2004, 46, 3761]. Write a structure for 1,5-hexadiyne [c (cal H; C: 13. \ m‘ ted—butylethylene H556 CM: CA4; CE C44 1 ,5-hexadiyne c. ( I 5) Consider the transformation below which was reported recently by chemists at the University of Kansas [Org Lett. 2004, 6, ”1205]. Assign systematic (IUPAC) names to each compound. Name: 235+ Kuwaiti—2‘ (a) ~ r- alum ~ 2‘ we Jews-n7! Ppu‘lfmfi. .-2- rém‘iatmf d. ( f 4) 4-Octyne (structure below) was utilized as a reactant in a recent study of the platinum catalyzed addition of alcohols to the triple bond [Tetrahedron Lerr. 2004, 45, 3787]. I (2) Write a structure for a weakly acidic isomer of 4-octyne. - (2) Write a structure for cyclic structural isomer of 4-octyne. I __ . CH3CH2CH2CZCCH2CH2CH3 ‘ Or]; ((3%) C: C/H i g ‘— 4—octyne ; acidic isomer ...
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