Question

I. SYNTHESIS. Use alkene and/or alkyne reactions to complete the following problems 1. Cyclooctyne is the smallest cycloalkyne which is stable at normal temperatures. Show the sequence of reactions need to complete the synthesis of the deuterium-labeled cyclooctanol shown below ((be careful with stereochemistry). Assume that any necessary reagents can be obtained in isotopic forms. 2. Show a reaction for the synthesis of disopropyl ether (below) using only propene, water and concentrated sulfuric acid. disopropyl ether 3. Hexane is a common solvent, but long-term occupational exposure to this compound is associated with a debilitating disease known as peripheral neuropathy. To study the distribution of this compound in experimental animals, the following tritium-labeled compound is needed. The radioactive "labels" in the molecule will allow pharmacologists to quantitatively assess the uptake of the compound in various biological tissues through a technique known as liquid scintillation counting (a common method for measuring radioactivity in a sample). The radiolabeled compound is not commercially available and must be synthesized. Starting with acetylene as the only available organic compound, but using any necessary inorganic reagents, show a sequence of reactions for synthesis of the compound. There is no stereochemistry implied in the structure above, so that is not a consideration in the synthesis.

Answer 1

The given cyuoоctune produи is payticuy Yeolu ceo us Ing Lindias coutalysi ( H21 Pdso2) Нydlsoboatto the using the isoloрic vpagent for DOliowel b4 Hao) He we охidcuhon reaution (иагоbочот) get desired poduit J BD3 indlai's fatahst Р2 д ВI paso |аsя Ио (sun add ihon) пе о оу \lhen he pTopene i s clconol Tuis lrono\ on * (onverteal into сonverheal into Тosing walt moleeule Иurhe Bay eney Нe s04g ca-cy- cug сси-о-оя -4, Сug - cut 3 cy ди Ои JAeunanism : — ит из ) yoм. -т

Synthesi's 2 ei 2 ea MaczCa 2NaBs H-CEC Mauy AcetyLene Ta 1Pdso c-ug C = 1 1 D