Questions dealing with alcohols

1. Propose a mechanism for the transformation of nerol into a -terpineol:





 

2. The sex attractant of the Douglas fir tussock moth has been synthesized via the following route:

  1-heptyne + LiNH₂ ® CH₃(CH₂)₄CºCLi

CH₃(CH₂)₄CºCLi + ClCH₂CH₂CH₂Br ® CH₃(CH₂)₄CºCCH₂CH₂CH₂Cl

CH₃(CH₂)₄CºCCH₂CH₂CH₂Cl ® CH₃(CH₂)₄CºCCH₂CH₂CH₂CH(OH)C₁₀H₂₁

CH₃(CH₂)₄CºCCH₂CH₂CH₂CH(OH)C₁₀H₂₁ ® CH₃(CH₂)₄CH=CHCH₂CH₂CH₂CH(OH)C₁₀H₂₁

CH₃(CH₂)₄CH=CHCH₂CH₂CH₂CH(OH)C₁₀H₂₁ ® CH₃(CH₂)₄CH=CHCH₂CH₂CH₂COC₁₀H₂₁

3. Testosterone undergoes dehydration as shown below. Propose a mechanism.



 

4.  Treatment of 4-hydroxycyclohexanone with 1 equivalent of CH₃MgBr gives no alcohol. Treatment with an excess of CH₃MgBr gives a good yield of 1-methyl-1,4-cyclohexanediol. Why?

 The Grignard reagent reacts with the H of the hydroxygroup of the 4-hydroxycyclohexanone to give methane. When all the H is used up in this fashion, the Grignard reagent reacts with the keto group to give the 1-methyl-1,4-cyclohexanediol

5. What are the products of the reaction of ethoxycyclohexane and aqueous HI?



 

6. When 4-chloro-1-butanol is treated with strong base (eg NaH), tetrahydrofuran (C₄H₈O) is formed.

Propose a mechanism.

 



 

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