Q2P-e - Organic Chemistry (Mcmurry)

Question

Draw structures corresponding to the following IUPAC names: (e) 4-sec-Butyl-2-chlorononane.

Step-by-Step Solution

Answer

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

Step 1: Alkyl Halides

Alkyl halides are also known as haloalkanes or halogenoalkanes. They contains one or more halogen substituents i.e. –Br, -Cl,-I,-F.

Step 2: Rules for 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 3: Structure of alkyl halides

(e) As the chemical name indicates, that the given alkyl halide is nonane, which means it has nine carbon atoms in the parent chain.

It is having two substituents i.e one sec-butyl group and one chloro group, so they will be assigned position alphabetically.  

The chloro group is positioned on number 2 and sec-butyl on number 4 carbon. The numbering is done from that end of the parent chain, from where the substituents possess lowest number. Thus, the given compound has following structure: