[whyohme]

how to get butanoic acid and hexanoic acid at the same time from 1-bromopentane?

Thanks!

[discodermolide]

how to get butanoic acid and hexanoic acid at the same time from 1-bromopentane?

Thanks!

Hexanoic acid is easy, butanoic acid need a bit more thought.
Have you any ideas?

[whyohme]

how to get butanoic acid and hexanoic acid at the same time from 1-bromopentane?

Thanks!

Hexanoic acid is easy, butanoic acid need a bit more thought.
Have you any ideas?

I came up with this. I have no idea how to obtain hexanoic acid. I dont find any example shows "more-carboned product" example. please help. thanks

[discodermolide]

That's OK for the first one.
The second one is you make a Grignard reagent with magnesium then treat it with CO₂. There the chain goes from 5 carbons to 6!

[orgopete]

You might want to check the reagents for the elimination so you don't get substitution, but otherwise fine.

Hexanoic acid hint, if bromopentane is made into a nucleophile, then what electrophile will give the acid upon workup?
A second option is if bromopentane is the electrophile, what one carbon nucleophile will give the same oxidation state as a carboxylic acid (it will give a carboxylic acid after hydrolysis)?

[whyohme]

That's OK for the first one.
The second one is you make a Grignard reagent with magnesium then treat it with CO₂. There the chain goes from 5 carbons to 6!

thank you

[whyohme]

You might want to check the reagents for the elimination so you don't get substitution, but otherwise fine.

Hexanoic acid hint, if bromopentane is made into a nucleophile, then what electrophile will give the acid upon workup?
A second option is if bromopentane is the electrophile, what one carbon nucleophile will give the same oxidation state as a carboxylic acid (it will give a carboxylic acid after hydrolysis)?

if bromopentane is electrophile, CO2 will be the nucleophile ?   

[orgopete]

No CO2 is an electrophile. The carbon will accept electrons, for example from a Grignard reagent. You need the carbon to possess electrons than can be donated. Hint, it is a one carbon nucleophile with a nitrogen attached.