What are the reactive organic groups in salbutamol?

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Discussion Overview

The discussion revolves around identifying the reactive organic groups in salbutamol, exploring their behavior under mild oxidation, and assessing the overall acidity or alkalinity of the molecule. It includes theoretical considerations and chemical reasoning.

Discussion Character

  • Homework-related
  • Technical explanation
  • Debate/contested

Main Points Raised

  • Some participants identify the hydroxyl group, benzene ring, amino group, and alkyl group as reactive organic groups in salbutamol, but express uncertainty about the correctness of this identification.
  • One participant suggests that the benzene and alkyl groups may not be considered reactive compared to heteroatoms.
  • There is a discussion about the oxidation of the hydroxyl group, with some stating it can be oxidized to a ketone or aldehyde.
  • Some participants question whether phenol can be oxidized under mild conditions, with differing opinions on its reactivity.
  • One participant mentions that phenols can be oxidized by air, while another argues that phenol would not oxidize under mild oxidizing agents.
  • There is a mention of the potential formation of antiaromatic products from the oxidation of phenolic groups, which could destabilize the molecule.

Areas of Agreement / Disagreement

Participants express differing views on the reactivity of phenolic groups and the conditions under which they can be oxidized. There is no consensus on the complete list of reactive groups or their behavior under oxidation.

Contextual Notes

Participants note the complexity of oxidation reactions and the influence of reaction conditions on the outcomes. There are unresolved questions regarding the specific reactivity of certain groups in salbutamol.

Who May Find This Useful

This discussion may be useful for students studying organic chemistry, particularly those interested in functional group reactivity and oxidation reactions.

Kushal
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Homework Statement



Salbutamol is as shown below. (i managed the display off google which is similar to that of the book)

http://upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Salbutamol-2D-skeletal.png/800px-Salbutamol-2D-skeletal.png"

except for the cyclic ring is a benzene ring in the book and the alkyl group to the roght of the nitrogen is represented as R. (R is an alkyl group which for the purpose of this question does not affect the rest of the molecule)

(a) Name four reactive organic groups in salbutamol.
(b) State 2 of these groups which are affected by mild oxidation, and what groups are produced.
(c) Would you expect the salbutamol molecule to be acidic, neutral or alkaline?


Homework Equations





The Attempt at a Solution



(a) i identified the hydroxyl group, benzene ring, amino group, and alkyl group.

But I'm not sure if this is correct.

(b) the hydroxyl group will be oxidised to either a ketone or an aldehyde by mild oxidation.

i can't find a second one.

(c) the molecule is alkaline because of the basic -NH- group
 
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(a) Amine not Amino group

(b) Benzyl Alcohol can be oxidized to benzoic acid as there is benzylic hydrogen present.
 
are there any other reactive groups in the molecule?
 
Kushal said:
(a) Name four reactive organic groups in salbutamol.
(b) State 2 of these groups which are affected by mild oxidation, and what groups are produced.
(c) Would you expect the salbutamol molecule to be acidic, neutral or alkaline?

The Attempt at a Solution



(a) i identified the hydroxyl group, benzene ring, amino group, and alkyl group.

But I'm not sure if this is correct.

I believe that the question is asking only for the reactive groups. That eliminates the benzene and the alkyl groups. Heteroatoms are generally regarded as more reactive than aromatic groups and alkyl groups.

(b) the hydroxyl group will be oxidised to either a ketone or an aldehyde by mild oxidation.

i can't find a second one.

What might you do with the phenol?
 
i don't think phenol can be oxidised. i read that somewhere in my notes...
 
i really don't know what to write besides these groups... :-s

maybe a phenolic group instead of the benzene ring.
 
Phenol wouldn't oxidize under mild conditions... it may have something to do with a property of benzene...

Both of the other OH groups are alcohols. One makes a ketone and one makes an aldehyde...
 
Google "phenol oxidation". First hit...
 
oo yeah, phenols CAN be oxidised...
 
  • #10
The first hit doesn't work; it brings me to a blank page.

I highly doubt that the phenyl OH group will be oxidized more readily than the primary and secondary alcohols, especially in the same conditions for these (such as Jones reagent or CrO3/H2SO4); the end product would be antiaromatic and destablilize the molecule. Nonetheless, it would produce a ketone.
 
  • #11
the phenol would not be oxidised by a mild OA
 
  • #12
Phenols are oxidized by AIR! That's pretty mild. Much more mild than chromium oxidation!
 
  • #13
Gannon said:
...the end product would be antiaromatic and destablilize the molecule. Nonetheless, it would produce a ketone.


Quinones are almost aromatic.
 
Last edited:
  • #14
aaaahh... ok... nice. i didn't know!
 

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