order of naming

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Diana Tran 3E
Posts: 19
Joined: Fri Sep 25, 2015 3:00 am

order of naming

Postby Diana Tran 3E » Tue Mar 01, 2016 8:09 pm

When numbering substituents, do you give the substituents with the most atomic mass the lowest number even if it would give the other two substituents a higher number, or do you just number the substituents based on the fact that you just want lower numbers?

Chem_Mod
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Re: order of naming

Postby Chem_Mod » Tue Mar 01, 2016 9:14 pm

You never use atomic mass to determine anything in numbering a chain. There are two ways to number a chain: left to right, or right to left. Use the direction which gives the lowest number overall (do NOT sum). Only in the case of a tie, will you give the lower number to the alphabetically-first group.

Diana Tran 3E
Posts: 19
Joined: Fri Sep 25, 2015 3:00 am

Re: order of naming

Postby Diana Tran 3E » Tue Mar 01, 2016 10:26 pm

If atomic mass is never taken into account, then how come for question 5 in the first quiz 3 preparation, the "bromo" substituent is given the bigger number (3) and the "iodo" substituent is given the smaller number (1) – even though it is a tie and if read left to right iodo would be 1 and bromo would be 3 OR if read right to left bromo would be 1 and iodo would be 3? The correct answer had bromo at 3 and iodo at 1. Why is this right if atomic mass doesn't matter and if during a tie you are supposed to prioritize the one higher on the alphabet?

Ronald Yang 2F
Posts: 86
Joined: Fri Sep 25, 2015 3:00 am

Re: order of naming

Postby Ronald Yang 2F » Tue Mar 01, 2016 10:49 pm

It's wrong. It's supposed to have 1-bromo-3-iodo. Priority only applies to alkenes in determining cis/trans, not for naming for numbering.


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