SOS~Ochem Addition Reaction

[linuxzhen]

---

Members do not see this ad.

How do 1,2- ,1.4- addition transpire?

 

[leaveit2rani]

I think it is D

 

[PostBaccHopeful]

How do 1,2- ,1.4- addition transpire?

I also think the answer is D, but I tried solving for C and I don't know if I did it correctly. The numbering on the image is definitely non-conventional and doesn't follow the rule, but this is the only way I thought would lead to the 1,2-1,4-,1,6-1,8-addition.

How did you come up with the 1,8-addition? I'm not even sure I did the others correctly.

 

[PostBaccHopeful]

I also think the answer is D, but I tried solving for C and I don't know if I did it correctly. The numbering on the image is definitely non-conventional and doesn't follow the rule, but this is the only way I thought would lead to the 1,2-1,4-,1,6-1,8-addition.

How did you come up with the 1,8-addition? I'm not even sure I did the others correctly.

Sorry, I tried uploading the image so it shows but it's not working. My previous response has an attached image but its not showing as full image like yours.

 

[PlumbLine]

How do 1,2- ,1.4- addition transpire?

Labeling the conjugated pi bonds from left to right as A, B, and C, a 1,8 addition would be a nucleophilic attack on the first (left most) carbon of A. 1,6 attack would be the the first carbon of B. and 1,4 attack would be to the first carbon of C. Note that in each case the pi-bonds right of the attack would be shifted right and you break the epoxide open. The oxygen breaks its bond with the "7th" carbon and stays bonded to the "8th". I believe a 1,2 attack would just be to open the epoxide avoiding the C=C pi bonds.

 

[dsoz]

I say D. There are 9 carbons that are SP^2 (all 8 in the double bonds +1 in the carboxylic acid end), and 11 that are SP^3.

Last time I checked, 9 was not greater than 11.

dsoz