ozonolysis: oxidative or reductive?

[BrownieDDD]

hi, i Know the conditions for oxidative ozonolysis is H202 and 03 while reductive ozonolysis is 03 and zn h20.

However, Kaplan test questions would say something like

What's the ozonolysis of trans-3m=-methlyl-2-pentene ?

How do i know if it's reductive or oxidative?

kaplan's answer: butanone and acetaldehyde ...which is reductive ozonolysis

. ...but i keep thinking oxidative ozonlysis. so i choose butanone and acetaldehyde.

I know some of you will say, oh well the DAT's orgo section isn't that complicated etc but what if i get a question that says what's the product after ozonlysis? ..the concept isn't that hard..but how would i know if it's reductive or oxidative? Even one question makes a difference on the DAT.

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[Subcharge]

To my understanding, its always oxidation. this is the first time I'm hearing of a reduction AND oxidation mechanism.

To my knowledge, it is always oxidation. You are converting an alkene to an aldehyde.

 

[BrownieDDD]

yeah, it is ALWAYS oxidation. but there are two kinds of oxidation when it comes to ozonlysis.

1. oxidative ozonlysis which oxidizes things like a double bond with an R and H on one side of the double to acetic acid

2. and reductive ozonlysis which oxidize things like a double bond with and R and H on one side of the double bond to aldehydes.

for some reason kaplan always refers to ozonolysis just that under reductive conditions.

but i'm wonderin if the DAT would point out reductive or oxidative ozonlyis.