ozonolysis

[Questions]

When alkene is reacted with 1) ozone, alkyl halide and then 2) Sodium borohydride and alcohol --> the result is a vic diol? is the double bond completely cleaved?

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[wantVCUdental]

When alkene is reacted with 1) ozone, alkyl halide and then 2) Sodium borohydride and alcohol --> the result is a vic diol? is the double bond completely cleaved?

I have never seen that reaction condition for ozonolysis, usually ozone is accompanied with a metal catalyst like zinc followed by an acid work up...

but if it's indeed an ozonolysis reaction, then YES, the double bonds are completely cleaved (for testing purposes).
And no you don't get a diol, you get 2 alcohol products. However, before you arrive at those alochols, you will make 2 carbonyl intermediates which are reduced by the sodium borohydride.

Hope that helps

 

[redchesus]

yeah, lysis generally means something gets cleaved

 

[kpanesar]

theres two reactions for ozonolysis w/ alkenes:

1) alkene reacted with 1) O3, CH2Cl2 // 2) Zn/HCl ----> cleaves the double bond to yield an aldehyde

2) alkene reacted w/ 1) O3, CH2Cl2 // 2) NaBH4, CH3OH ----> cleaves the double bond to yield primary alcohols

 

[redchesus]

theres two reactions for ozonolysis w/ alkenes:

1) alkene reacted with 1) O3, CH2Cl2 // 2) Zn/HCl ----> cleaves the double bond to yield an aldehyde

2) alkene reacted w/ 1) O3, CH2Cl2 // 2) NaBH4, CH3OH ----> cleaves the double bond to yield primary alcohols

well yeah, you would know the second one just by knowing the first one and that NaBH4 is a reducing agent (something you have to know anyway)