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Naming/ Drawing Exercises. 2,2,6,7-tetramethylnonane. 1. 2. 3…. Careful with the parent chain!!! Don’t be fooled by the seeming 1-tert-butyl group LOL. 3-ethyl-4-isopropyl-2,5-dimethylheptane. 7. 3. 2. 1.

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2 2 6 7 tetramethylnonane
2,2,6,7-tetramethylnonane

1

2

3…

Careful with the parent chain!!! Don’t be fooled by the seeming 1-tert-butyl group LOL.


3 ethyl 4 isopropyl 2 5 dimethylheptane
3-ethyl-4-isopropyl-2,5-dimethylheptane

7

3

2

1

The trick here is to remember WE PREFER HAVING MORE BRANCHING when we find 2 or more possible parent chains.


3 3 6 triethyl 6 methyloctane
3,3,6-triethyl-6-methyloctane

2

1

3

Since we can’t reduce numbering either way (3,3,6,6) WE NOW CHOOSE NUMBERING WITH ALPHABETICAL PRIORITY… smaller numbers for ‘e’ in ethyl than ‘m’ for methyl.


1 1 2 triethyl 2 methylcyclopentane
1,1,2-triethyl-2-methylcyclopentane

Since we can’t reduce numbering either way (1,2 or 2,1) WE NOW CHOOSE NUMBERING WITH ALPHABETICAL PRIORITY… smaller numbers for ‘e’ in ethyl than ‘m’ for methyl.


1 ethyl 1 2 4 trimethyl 4 propan 2 yl cyclohexane or 1 ethyl 4 isopropyl 1 2 4 trimethylcyclohexane
1-ethyl-1,2,4-trimethyl-4-(propan-2-yl)cyclohexane or 1-ethyl-4-isopropyl-1,2,4-trimethylcyclohexane



Most stable form1
Most stable form?

ETHYL Too bulky for axial!

H

ISOPROPYL also too bulky


More stable
More Stable?

H

After a RING FLIP, the bulkier groups are now along the EQUATORIAL POSITION, with less steric strain, because the bulky groups are all pointing out of the ring, and not “blocking” other groups/ having repulsions with other electron clouds.