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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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- Spring '10
- Organic chemistry