[Rutherford]

From the given reagents, what could you use to distinguish between the following compounds (1 reagent for 1 pair):
a)benzyl-alcohol and phenol
b)1-butanol and 2-methyl-2-butanol
c)acetaldehyde and acetone
d)acetophenone and benzophenone

Reagents:
1.CuSO₄/NaOH
2.FeCl₃
3.I₂+NaOH
4.K₂Cr₂O₇

I don't understand how the specified reagents are used to distinguish between certain compounds, what are the products (I suppose that it is all about their different behavior)?

[discodermolide]

From the given reagents, what could you use to distinguish between the following compounds (1 reagent for 1 pair):
a)benzyl-alcohol and phenol
b)1-butanol and 2-methyl-2-butanol
c)acetaldehyde and acetone
d)acetophenone and benzophenone

Reagents:
1.CuSO₄/NaOH
2.FeCl₃
3.I₂+NaOH
4.K₂Cr₂O₇

I don't understand how the specified reagents are used to distinguish between certain compounds, what are the products (I suppose that it is all about their different behavior)?

Well presumably one reagent will only react with one of the compounds in the compound pairs. So you need to look and see which reacts.

[Rutherford]

Didn't think in that way .
Okay, using your tip, 1st I saw that b) can be distinguished with the dichromate. I suppose that by CuSO₄/NaOH is meant some kind of Grignard's reagent, so it can be used for c). Now, 2 reagents and 2 pairs left and I really can't think of how they can be combined. I don't know what FeCl₃ alone can do, and first time I see iodine and NaOH together as a reagent. Maybe NaOH reacts with phenol and not with benzyl-alcohol, but why is I₂ used?

[Arkcon]

Raderford:, if you think CuSO₄/NaOH is a Grignard's reagent, then I think that you're not trying to figure it out at all, and are just spouting buzzwords.

http://en.wikipedia.org/wiki/Copper%28II%29_hydroxide#Reagent_for_organic_chemistry

[discodermolide]

Didn't think in that way .
Okay, using your tip, 1st I saw that b) can be distinguished with the dichromate. I suppose that by CuSO₄/NaOH is meant some kind of Grignard's reagent, so it can be used for c). Now, 2 reagents and 2 pairs left and I really can't think of how they can be combined. I don't know what FeCl₃ alone can do, and first time I see iodine and NaOH together as a reagent. Maybe NaOH reacts with phenol and not with benzyl-alcohol, but why is I₂ used?

pair B are both alcohols, how can an oxidiser distinguish between them, it can't.
Iodine and NaOH are used in an important reaction for certain types of carbonyl compound, which you have here.

[Rutherford]

Raderford:, if you think CuSO₄/NaOH is a Grignard's reagent, then I think that you're not trying to figure it out at all, and are just spouting buzzwords.

http://en.wikipedia.org/wiki/Copper%28II%29_hydroxide#Reagent_for_organic_chemistry

Oh my  , I've meant Fehling's reagent, but wrote Grignard's. Sorry for this stupid mistake.

The oxidizer can distinguish between those alcohols because one is tertiary.
You probably mean that NaOH and I₂ are used for d), but what is the reaction? FeCl₃ then left for pair a), what is the reaction here?

[discodermolide]

Raderford:, if you think CuSO₄/NaOH is a Grignard's reagent, then I think that you're not trying to figure it out at all, and are just spouting buzzwords.

http://en.wikipedia.org/wiki/Copper%28II%29_hydroxide#Reagent_for_organic_chemistry

Oh my  , I've meant Fehling's reagent, but wrote Grignard's. Sorry for this stupid mistake.

The oxidizer can distinguish between those alcohols because one is tertiary.
You probably mean that NaOH and I₂ are used for d), but what is the reaction? FeCl₃ then left for pair a), what is the reaction here?

Look up the iodoform reaction for d.
What does FeCl₃ do to phenols but not alcohols?

[Rutherford]

"What does FeCl3 do to phenols but not alcohols?"
Right, they give colored complexes.
"Look up the iodoform reaction for d."
Found this: http://en.wikipedia.org/wiki/Haloform_reaction it says that the reaction can only be applied to methyl ketones, and acetophenone is one. So, everything is clear now I think. Thanks again for the help.

[discodermolide]

"What does FeCl3 do to phenols but not alcohols?"
Right, they give colored complexes.
"Look up the iodoform reaction for d."
Found this: http://en.wikipedia.org/wiki/Haloform_reaction it says that the reaction can only be applied to methyl ketones, and acetophenone is one. So, everything is clear now I think. Thanks again for the help.

No problem.

[camptzak]

I understand the mechanism for the ferric chloride/phenol reaction. why could this work for a regular alcohol? couldnt the OH group still displace a chlorine which would in turn remove the OH proton?