DAT destroyer orgo #106 and 118

[diene]

I have the 2011 version...
106- which compound will dissolve in concentrated HBr or HCl but not in water?

a. octanal b. 2-octanone c. 2-octananmine d. 1,2 - diethybenzene e. 2-octanol

The answer is c but I am not quite understanding this...what reaction takes place with HCl vs. water with an amine?

118- i converted the newman projection to a fischer projection but my H and Cl on the second carbon were opposite of what it is supposed to be (based on the solution). My fischer projection looked like the original fischer projection. My question is why is the Cl on the right side on the second carbon? From looking at the newman projection, I thought it should be on the left??

---

Members don't see this ad.

 

[diene]

anyone?

 

[jwest88]

I'm not sure on the second one.(I don't have the 2011 version) But for the first question, amines that are longer than 3 carbons are not water-soluble unless they're charged. Amines are bases and will pick up a proton becoming R-NH3+ which is then soluble because it's charged.

 

[HappyDentist90]

For 118, anytime you convert a Newman into a Fischer the substituents attached to the carbon in the back must be switched (as stated in the destroyer).

 

[biomolecmed]

For 106, the answer is E, because Octanol has too many carbons and therefore not water soluble However, when in HBr or HCl, it can be protonated to yield oxonium ion which has a plus charge. This will make it soluble.

For 118, whenever you convert newman to fisher, you always switch side substituents on the back carbon.

Hope this helps. Good luck.