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Topic: Product from reaction of Citral with Br2/CH2Cl2  (Read 9988 times)

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Offline ckg115

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Product from reaction of Citral with Br2/CH2Cl2
« on: October 07, 2012, 02:52:47 PM »
What type of product is expected from the reaction of citral with Br2/CH2Cl2? with chromic acid?

I have the answer, I'm just looking for the proper method for solving the problem. Would anyone be able to give me overview of what happens in the reaction and how they came to the product? What should I study up on to better understand?

I feel like I just don't know where to start  :-\
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Offline sjb

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Re: Product from reaction of Citral with Br2/CH2Cl2
« Reply #1 on: October 07, 2012, 03:02:21 PM »
Quote from: ckg115 on October 07, 2012, 02:52:47 PM
What type of product is expected from the reaction of citral with Br2/CH2Cl2? with chromic acid?

I have the answer, I'm just looking for the proper method for solving the problem. Would anyone be able to give me overview of what happens in the reaction and how they came to the product? What should I study up on to better understand?

I feel like I just don't know where to start  :-\

What functionality does citral have? How do these react with the reagents you have listed?
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Offline ckg115

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Re: Product from reaction of Citral with Br2/CH2Cl2
« Reply #2 on: October 07, 2012, 03:16:51 PM »
Citral structural formula is (CH3)2C=CH-CH2-CH2-C(CH3)=CH-CHO so it has an aldehyde functional group on the end.
I know with bromine, bromine only reacts over carbon double bonds.
I'm not sure how the dichloromethane comes in though...
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Offline discodermolide

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Re: Product from reaction of Citral with Br2/CH2Cl2
« Reply #3 on: October 07, 2012, 04:30:26 PM »
Dichloromethane is an inert solvent.

What does the chromic acid do?
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Offline ckg115

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Re: Product from reaction of Citral with Br2/CH2Cl2
« Reply #4 on: October 07, 2012, 06:37:33 PM »
Chromic Acid oxidizes primary and secondary alcohols and aldehydes and does not oxidize the carbon double bonds.

If it helps
The products I found for the answer are

2,3,6,7-tetrabromo-3,7-dimethyloctanal for the Citral reaction with bromine

3,7-dimethylocta-2,6-dienoic acid for the Citral reaction with Chromic Acid

I just cant figure how these answers were worked
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Offline discodermolide

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Re: Product from reaction of Citral with Br2/CH2Cl2
« Reply #5 on: October 07, 2012, 06:44:48 PM »
So what products would you expect from the reaction with bromine?
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Offline discodermolide

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Re: Product from reaction of Citral with Br2/CH2Cl2
« Reply #6 on: October 07, 2012, 11:01:18 PM »
Quote from: ckg115 on October 07, 2012, 06:37:33 PM
Chromic Acid oxidizes primary and secondary alcohols and aldehydes and does not oxidize the carbon double bonds.

If it helps
The products I found for the answer are

2,3,6,7-tetrabromo-3,7-dimethyloctanal for the Citral reaction with bromine

3,7-dimethylocta-2,6-dienoic acid for the Citral reaction with Chromic Acid

I just cant figure how these answers were worked


These answers are ok.
Start with the bromine reactions. What happens when bromine adds across a double bond? What happens first in the mechanism?
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