Q2P-a - Organic Chemistry (Mcmurry)

Question

Draw structures corresponding to the following IUPAC names: (a) 2-Chloro-3,3-dimethylhexane.

Step-by-Step Solution

Answer

 (a)The structure of the compound (a) is given below:

Step 1: Nomenclature of Alkyl halides

IUPAC rules used for naming of Alkyl halides

• Select longest carbon chain, it is the parent chain;
• Longest chain must contain double or triple bond, if present;
• Number the alkyl or halo substituent carbon i.e. it should possess lowest number in the parent chain;
• Assign a number to each substituent;
• Write the name of substituent’s in alphabetical order while naming;

Step 2: Structure of alkyl halides

(a) As the chemical name indicates, that the given alkyl halide is hexane, which means it has six carbon atoms in the parent chain.

It is having three substituents i.e. two methyl groups and one chloro group, so they will be assigned position alphabetically.  

The chloro group is positioned on number 2 and methyl on number 3 carbon. Since, the name indicates two methyl groups on C3, so it is 3,3-dimethyl. Thus, the given compound has following structure: