Question

One compound that contributes to the "seashore smell" at beaches in Hawaii is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane.Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, OHCCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'? Part 1 out of 2 How many chiral double bonds does dictyopterene D' possess? How many stereogenic carbons exist for dictyopterene D'? A total of stereoisomers are possible for dictyopterene D'.

Answer 1

Answer:

Explanation:

There are few simple rules in organic chemistry which a person must learn.

1. In predicting a structure from ozonolysis, number of oxygen present in products must be counted. In this particular example, there are 2+3+1 = 6 oxygen atoms are present in three molecules. This means that there should be at least three confirmed double bonds must be present in the molecule of Dictyopterene.

2. There are in total of 3+5+3 = 11 carbon atoms present, making 2^11 = 2048 possible structures for this particular structure. But since there are three double bonds present, this will reduce the number of possible structures as well.

3. Questions also says that when fully hydrogenated, the molecule generates Butylcycloheptane. That means that our base molecule is Butylcycloheptane and this molecule contains at least three double bonds.

So, first we draw the molecule of butylcycloheptane. After this, we think of were double bonds could be present. We do have the products. Let's make their structures first. I have also mentioned the possible breakup where the ozonolysis has occured by color code. You can see them in the reference image attached.

Part 1 out of 2: There is only one chiral carbon present in the molecule and have two possible isomers. Cis and Trans. Only one stereogenic carbon is present, that's why two possible isomers. Image attached.