Question

Problem #3 Show how you would synthesize the compound represented in the Fischer projection below starting from acetylene. You may use any other reagent necessary. HC-OH HC-OH Extra Credit When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give 7-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the products shown below. Propose a structure for X.

Answer 1

NaNH22 Н - СЕС-н EDA. FC- H CH₃ I (ler) OH CH₂-CECCA он BH₂. THE THE Ph CH3 13 X ) ph w H₂ , Pd/cacoz Lindlar's catalyst он H. BI cis - hydrogenated magor product H₂C - CA CHqPh Y H202/Nant favorable approach because of coordination of "Be with allylic -OH) H3C- H₂4 -OH СМ2 both -ot remain on the same side Extra credit & That 5 eq. of H₂/Pd n-butyl-cyclo- means herane, 5 unsaturation (double of triple bond) is present in x. 03 IOMS (excess) "T Ho + H H&H acid and co produced means terminal -CEC-H present.

ring and a So ex has a -CECH functional six membered group Now the ozonolysis double bonded fragments products can be found from the as followers 0 0 40 = 7 - members 0 0 4 0 →6-membered ring HGH draw a structure So now if we for X -=-H H2opt 5 ch (X w - butys syclohexane. 03 Dins + H OH + coz
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