A2 Chemistry assignment (help needed)

Okay, I had to prepare prop-2-enyl hexanote.
Is there another common name for this? I've searched on google and haven't found anything on the product's spectras (IR and NMR)
Could somebody help?

Reply 1

Aired

Do you know the structure?

Edit: It's alternate name is "allyl caproate" apparently.

The structure is CH2=CH-CH2-OOC[CH2]4-CH3

Reply 2

oxymoron

Widowmaker

Okay, I had to prepare prop-2-enyl hexanote.
Is there another common name for this? I've searched on google and haven't found anything on the product's spectras (IR and NMR)
Could somebody help?

do you mean hexanoate rather than hexanote? that would make it an ester between hexanoic acid and CH3CH2CHOH (ie propanol with a double bond)

Reply 3

Christophicus

oxymoron

do you mean hexanoate rather than hexanote? that would make it an ester between hexanoic acid and CH3CH2CHOH (ie propanol with a double bond)

yes, typing error.
My stupid teacher made us use butanoic acid and started blaming my chem partner and I as to why it wasn't smelling of pineapples. i worked it out and realised why. We should have used hexanoic acid.
Another odd thing happened. We used PCl5 and added it to the acid to form an acid chloride (butyl chloride). Then I heated it under reflux with the alcohol I think. Then I distilled the product to purify it by adding a drying agent.
I worked out the masses of the liquids and worked out what my maximum yield should have been (for the first bit) and the amount I got exceeded it!
My teacher checked it and saw nothing wrong with my calculation. A bit of a disaster really! I have to write it up but i'm having loads of problems.

Reply 4

oxymoron

Widowmaker

yes, typing error.
My stupid teacher made us use butanoic acid and started blaming my chem partner and I as to why it wasn't smelling of pineapples. i worked it out and realised why. We should have used hexanoic acid.
Another odd thing happened. We used PCl5 and added it to the acid to form an acid chloride (butyl chloride). Then I heated it under reflux.
I worked out the masses of the liquids and worked out what my maximum yield should have been (for the first bit) and the amount I got exceeded it!
My teacher checked it and saw nothing wrong with my calculation. A bit of a disaster really! I have to write it up but i'm having loads of problems.

There's nothing wrong with your amount exceeding the theoretical maximum - it just means your sample isn't pure and it is the impurities that bump up the perceived yield.
How did you purify it? distillation? If so, maybe there is something else (one of the starting products maybe or a side reaction product?) with a similar boiling point to the product.

Also butanoic acid smells disgusting so I'm not surprised you didn't smell any pineapple smell :p:

Reply 5

Christophicus

oxymoron

my teacher thought it was a pretty hard practical. Took me about 4-5 hours.

Reply 6

Christophicus

oxymoron

In the end, it did actually smell fruity, but not pineapple smell. it probably had a different structure.

Reply 7

oxymoron

Widowmaker

In the end, it did actually smell fruity, but not pineapple smell. it probably had a different structure.

Yeah, you probably got the butanoate if you started with butanoic acid?

Reply 8

Christophicus

oxymoron

Yeah, you probably got the butanoate if you started with butanoic acid?

most likely. I'm sure my chemistry teacher was getting worked up over nothing. I'll ask him when I go back if I can borrow his computer program. it has literally every spectra for the products we made.

Reply 9

Christophicus

okay does anyone know the common name for prop-2-enyl butanoate?
The common name for prop-2-enyl hexanoate is allyl caproate. I get no hits from google with the proper name.

Reply 10

oxymoron

Widowmaker

okay does anyone know the common name for prop-2-enyl butanoate?
The common name for prop-2-enyl hexanoate is allyl caproate. I get no hits from google with the proper name.