Question 9 1,2-Trans-cyclohexanediol cyclopropanation of allylic ethers as shown in the scheme below. Ph Et₂Zn + CICH₂l Toluene 3 h, -20°C OH Ph and PhLi + НО THF -100°C (a) Draw the structure of the zinc reagent formed from Et2Zn the structure of the zinc reagent formed from Etz m ultimate formation of the cyclopropene ring. has been shown to be an efficient support for the asymmetric OH Bu₂NI TI₂O CH₂Cl₂ and CICH₂I that allows for the Et:Zn and CICH:I that allows f

Organic Chemistry
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Chapter18: Ethers And Epoxides; Thiols And Sulfides
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Question 9
has been shown to be an efficient support for the asymmetric
1,2-Trans-cyclohexanediol
cyclopropanation of allylic ethers as shown in the scheme below.
Et₂Zn + CICH₂l
Toluene
3 h, -20°C
Bu NI
TI₂O
CH₂Cl₂
and=a
PhLi
THF
-100°C
(a) Draw the structure of the zinc reagent formed from EtzZn and CICHal that allows for the
ultimate formation of the cyclopropene ring.
(b) The zinc reagent gives the 'active' organic molecule that completes the ring formation. Draw the
structure of this 'active' molecule.
(c) What name is given to each of your answers to parts (a) and (b).
The complex in part (a) can be described as a...
The molecule in part (b) can be described as a...
Page 17 of 18
Question 9 continued..
(d) The final step of the reaction sequence uses PhLi.
Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction
would occur.
Transcribed Image Text:Question 9 has been shown to be an efficient support for the asymmetric 1,2-Trans-cyclohexanediol cyclopropanation of allylic ethers as shown in the scheme below. Et₂Zn + CICH₂l Toluene 3 h, -20°C Bu NI TI₂O CH₂Cl₂ and=a PhLi THF -100°C (a) Draw the structure of the zinc reagent formed from EtzZn and CICHal that allows for the ultimate formation of the cyclopropene ring. (b) The zinc reagent gives the 'active' organic molecule that completes the ring formation. Draw the structure of this 'active' molecule. (c) What name is given to each of your answers to parts (a) and (b). The complex in part (a) can be described as a... The molecule in part (b) can be described as a... Page 17 of 18 Question 9 continued.. (d) The final step of the reaction sequence uses PhLi. Provide a reason and possible mechanism by which this final elimination and hydrolysis reaction would occur.
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