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Chapter 2: Problem 24

Draw structural formulas and write IUPAC names for the nine constitutional isomers with the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{16 \text { if }}\) -

Short Answer

Expert verified
Question: List the IUPAC names of the nine constitutional isomers of the molecular formula C7H16. Answer: The nine constitutional isomers of C7H16 are: 1. Heptane 2. 2-methylhexane 3. 3-methylhexane 4. 2,3-dimethylpentane 5. 2,4-dimethylpentane 6. 3,4-dimethylpentane 7. 2,2,3-trimethylbutane 8. 2,3,3-trimethylbutane 9. 3,3-dimethyl-2-methylbutane

Step by step solution

01

Draw the first isomer with all 7 carbons in a straight chain

Start with a backbone consisting of 7 carbon atoms connected linearly: \(CH_{3} - CH_{2} - CH_{2} - CH_{2} - CH_{2} - CH_{2} - CH_{3}\) This is called heptane.
02

Remove one carbon from the end and place it as a branch on the second carbon

We can create branching chain isomers by removing a carbon from the end and adding it as a branch on one of the other carbons in the main chain. Here, remove a carbon from one end and make a branch on the second carbon: \(CH_{3} - CH(CH_{3}) - CH_{2} - CH_{2} - CH_{2} - CH_{2} - CH_{3}\) This is called 2-methylhexane.
03

Place the branch on the third carbon

Next, we can move the branch to the third carbon: \(CH_{3} - CH_{2} - CH(CH_{3}) - CH_{2} - CH_{2} - CH_{2} - CH_{3}\) This is called 3-methylhexane.
04

Remove one more carbon from the main chain and place it as a branch

Now, remove one more carbon from the main chain and place it as a branch on the second carbon: \(CH_{3} - CH(CH_{3}) - CH_{2} - CH(CH_{3}) - CH_{2} - CH_{2} - CH_{3}\) This is called 2,3-dimethylpentane.
05

Place the second branch on the third carbon

Next, move one branch to the third carbon: \(CH_{3} - CH_{2} - CH(CH_{3}) - CH(CH_{3}) - CH_{2} - CH_{2} - CH_{3}\) This is called 2,4-dimethylpentane.
06

Place the second branch on the fourth carbon

Now, move one branch to the fourth carbon: \(CH_{3} - CH_{2} - CH_{2} - CH(CH_{3}) - CH(CH_{3}) - CH_{2} - CH_{3}\) This is called 3,4-dimethylpentane.
07

Remove one more carbon from the main chain and place it as a branch

Remove one more carbon from the main chain and add it as a branch on the second carbon: \(CH_{3} - CH(CH_{3}) - CH_{2} - CH(CH_{3}) - CH(CH_{3}) - CH_{2} - CH_{3}\) This is called 2,2,3-trimethylbutane.
08

Place the third branch on the third carbon

Move one branch to the third carbon: \(CH_{3} - CH_{2} - CH(CH_{3}) - CH(CH_{3}) - CH(CH_{3}) - CH_{2} - CH_{3}\) This is called 2,3,3-trimethylbutane.
09

Place the third branch on the fourth carbon

Finally, move one branch to the fourth carbon: \(CH_{3} - CH_{2} - CH_{2} - CH(CH_{3}) - CH(CH_{3}) - CH_{3} - CH_{3}\) This is called 3,3-dimethyl-2-methylbutane. Now, we have found a total of 9 constitutional isomers for the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{16}\) with their IUPAC names: 1. Heptane 2. 2-methylhexane 3. 3-methylhexane 4. 2,3-dimethylpentane 5. 2,4-dimethylpentane 6. 3,4-dimethylpentane 7. 2,2,3-trimethylbutane 8. 2,3,3-trimethylbutane 9. 3,3-dimethyl-2-methylbutane

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