Question

4-chloro-3, 4-dimethylnonan-1-amine

Assignment 3: Chiral Carbons and Stereoisomers On a page titled Chiral Carbons draw using a chemical drawing program or other computer generated form the expanded structure of your molecule. No hand drawn structures will be accepted. O Determine if your molecule contains any chiral carbons. If there are chiral carbons in your molecule, circle or highlight all of them. If your molecule does not contain any chiral carbons explain why none of the carbons are chiral. One a page titled Stereoisomers draw using a chemical drawing program or other computer generated form the expanded structure of your molecule. No hand drawn structures will be accepted. o Calculate the maximum number of possible stereoisomers of your molecule using the following formula: . Maximum number of possible stereoisomers = 2" (where n-the number of chiral carbons in your molecule). This calculation does not include E-or Z- isomers for any compounds containing double bonds o Draw the possible stereoisomers of the molecule using a chemical drawing program or other computer generated form. No hand drawn structures will be accepted. . Note that E-, Z- isomers of each stereoisomer are also possible and would not be accounted for by the formula above; draw any E- or Z- isomers.

Answer 1

Chiral Carbons: NH2 Hąc CH3 4-chloro-3,4-dimethylnonan-1-amine Chiral carbons are the carbon attached to 4 different groups. There are 2 chiral carbons. Please note that for a better understanding I am not drawing expanded structures as it mixup all the bonds and molecule is a large molecule. Stereoisomers: Max. possible stereoisomers = 2^n = 2^2 = 4 There is no C=C present in the molecule and hence not EIZ isomers. al CH₂ RANH2 HNS H2C CH3 Distereomers I CH2 Distereomers Enantiomers RA NHA HẠN SAR нс H CH3 Enantiomers

Hydrogen bonding with water: alel H H CH3 CI. Н.С I-Z:---- Amine -NH2 can act as receiver as nitrogen has lone pair of electrons and donor as N-H bond is polar bond. Polarity and solubility: CH3 polar group NH2 H2C CH3 The molecule contains one polar amino group and that is capable of forming hydrogen bonding with the water molecule. However, the major portion of molecule is hydrocarbon and C-Cl hence that major portion act as hydrophobic portion and makes it water insoluble.