[discodermolide]

Thank you. The problem I have is forming the actual ring, I form the enolate ion on the bottom aldehyde. I then count the carbons number 1 being the carbon bonded to the negatively charged oxygem, number 6 being the carbon of the other aldehyde, that gives me 6. How do I correctly number the carbons when forming rings?

It does not matter here where the enolate is formed as it is symmetrical. It is the enolate carbon which reacts not the carbonyl carbon.
Try again before I post the answer.

[Twickel]

I am obviously doing something wrong when closing the ring, as I can not get the carbonyls to be alpha to one another, so I can not form the final conjugated product.

[discodermolide]

I am obviously doing something wrong when closing the ring, as I can not get the carbonyls to be alpha to one another, so I can not form the final conjugated product.

You are closing the ring with the wrong carbon! In your drawing it is carbon number 1 which attacks the other aldehyde.
Try again before I post the answer

[Twickel]

but is carbon 1 not the negatively charged carbon?

If I draw a resonance diagram, I thought it was the alpha carbon which is negatively charged, now I got that carbon bonded to five things again.

[discodermolide]

but is carbon 1 not the negatively charged carbon?

If I draw a resonance diagram, I thought it was the alpha carbon which is negatively charged

It is the carbon at the end of the enolate C=C-O^- which attacks.
Try again before I post the answer.

[Twickel]

I hope this is it. i had to scribble around so the scanner would scan everything.

[discodermolide]

Bingo it doesn't look bad.
Here is my scheme, without the curly arrows which you can put in.

[Twickel]

Thank you, I now know it is much easier to draw the enolate, with the negative charge on the carbon, rather then on the oxygen, but only for intra molecular reactions....

 Mind helping me with one more questions? Its in the thread but I need to re write its been lost.

[discodermolide]

Thank you, I now know it is much easier to draw the enolate, with the negative charge on the carbon, rather then on the oxygen, but only for intra molecular reactions....

 Mind helping me with one more questions? Its in the thread but I need to re write its been lost.

Re-write it , but I have to go out soon so don't expect a rapid answer.

[Twickel]

Cyclopentanone reacts with i) NaOEt/ EtoCO2Et/ dry EtOH

ii) CH3I

iii) H+/H20/Heat

What is the product?

[discodermolide]

Cyclopentanone reacts with i) NaOEt/ EtoCO2Et/ dry EtOH

ii) CH3I

iii) H+/H20/Heat

What is the product?

What is the diethyl carbonate EtOCO2Et doing here? Make the enolate from cyclopentanone and take it from there!

[Twickel]

Sorry for the late reply, thats the thing I dont know what the ester does.. is it an acid?

[discodermolide]

Sorry for the late reply, thats the thing I dont know what the ester does.. is it an acid?

No it is not an acid it's an electrophile. React the cyclopentanone enolate with the carbonyl of the diethyl carbonate and see what you get.

[Twickel]

Ok, if that is right, where do I attack the CH3 from

[discodermolide]

Ok, if that is right, where do I attack the CH3 from

In your product draw it as an ester then see where you go next. Look at my picture and compare yours!