2009 Sample DAT: OChem #73

[airbmac7]

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Really confused on this question. If it's trans-1-chloro-4-methylcyclohexane, wouldn't the larger one (methyl) be equatorial and the chlorine axial? How come the marked answer choice (E) has them both equatorial? Am I missing something really simple here?

Any advice would be appreciated!

 

[Roy Williams]

Really confused on this question. If it's trans-1-chloro-4-methylcyclohexane, wouldn't the larger one (methyl) be equatorial and the chlorine axial? How come the marked answer choice (E) has them both equatorial? Am I missing something really simple here?

Any advice would be appreciated!

Since its trans, that just means one has to be up and the other down. Start with the methyl at the equatorial position as 1. 2 is axial, 3 is equitation, 4 is axial (these numbers are for substituants to all on the same face). So since a substituant on the same face as the methyl four spots away is axial, that means the chlorine is Equatorial since it is on opposite face (trans).

Sorry kinda rambled from my phone. Let me know if I need to explain it better.

 

[airbmac7]

Ahh you're right. I now remember Chad saying the same thing. Thanks!