Chalk−1

Chemistry · General chemistry II · Worked example

Name a branched alkane

Name the alkane (CH₃)₂CHCH₂CH(C₂H₅)CH₂CH₂CH(CH₃)₂.

Find the longest chain

The longest continuous chain runs from one end methyl, through the carbon with the ethyl group, to the other end: eight carbons, so the parent is octane.

Name the branches

Off the eight-carbon chain hang one ethyl group and two methyl groups.

Number the chain

From one end the branches are at 2, 4 and 7; from the other end, at 2, 5 and 7. The first point of difference is 4 against 5, so number from the end that gives 2, 4, 7.

The two ways to number the chain
DirectionMethylEthylBranch numbers
From the left2, 742, 4, 7
From the right2, 752, 5, 7

Write the name

Ethyl comes before methyl in alphabetical order, and the two methyl groups become 2,7-dimethyl.

4-ethyl-2,7-dimethyloctane

Result

4-ethyl-2,7-dimethyloctane.

Your turn

Name CH₃CH₂CH(CH₃)CH₂CH₂CH₃.

Show the answer and explanation

3-methylhexane.

The longest chain has six carbons (hexane), with a methyl group on the third carbon from the nearer end. Calling it 2-ethylpentane uses a five-carbon chain that isn’t the longest, and 4-methylhexane numbers from the wrong end.

Keep exploring

Draw it in the Skeletal tool with the name set as its target, turn Check on, then change the target to 5-ethyl-2,7-dimethyloctane: it still describes the structure, but it isn’t the systematic name, because the chain is numbered from the wrong end.

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Sources and scope

Authored study material. Tool results depend on the stated inputs and model assumptions.

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Try in the workspace

Open the example inputs, change a value and keep a useful result on your board.

Draw it and check the name Check the name 2-ethylpentane on 3-methylhexane See 3-methylhexane in every representation Open worked example on a board Organic nomenclature in Chemistry Reference

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