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Topic: synthesizing 1-phenylethanol  (Read 17065 times)

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Offline Steenrod

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Re: synthesizing 1-phenylethanol
« Reply #15 on: November 07, 2012, 01:20:52 PM »
@above, orgopete,I apologize for asking so many elementary questions which reflect a lack of understanding of organic chemistry. The course at my school provides little room for reaction mechanisms and instead focusses on synthesis.In absence of adequate knowledge about how things happen, I am never sure or I never know what to do unless I have seen a similar reaction.

I sincerely apologize again as things have come to a point where I do feel humiliated to ask questions without showing any effort.All the same, come December, I shall start with the book by  Francis Carey and study the subject from the scratch.Please show some patience as you have done for a few more days when my exams will be over and I shall have more time to understand things.  :(
I am horrible at chemistry.I am always liable to fail my chemistry exams.So, sorry for stupid questions.

Offline orgopete

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Re: synthesizing 1-phenylethanol
« Reply #16 on: November 08, 2012, 12:00:52 AM »
Let me guess:

Benzene+[itex]AlCl_3+Cl_2[/itex]=chlorbenzene which reacts with [itex]Mg[/itex] to give phenyl magnesium chloride .What next?

Okay so far. Now you need two different two carbon fragments to react with the Grignard to give the products.
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Offline discodermolide

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Re: synthesizing 1-phenylethanol
« Reply #17 on: November 08, 2012, 03:16:07 AM »
If you go to the link I posted you will see the following:
"Synthesis
Phenethyl alcohol can be prepared by a variety of procedures, such as by a Grignard reaction between phenylmagnesium bromide and ethylene oxide:

    C6H5MgBr + CH2CH2O → C6H5CH2CH2OMgBr
    C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH

However, the Friedel-Crafts reaction between benzene and ethylene oxide may also be employed:

    C6H6 + CH2CH2O (+ AlCl3) → C6H5CH2CH2OH (+AlCl3)

Phenethyl alcohol can also be prepared by biotransformation from L-phenylalanine using immobilized yeast Saccharomyces cerevisiae."
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Offline AWK

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Re: synthesizing 1-phenylethanol
« Reply #18 on: November 08, 2012, 09:33:28 AM »
In both reaction a different isomer is formed. But a correct one can be obtained from the Grignard compound with acetaldehyde.
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Offline blackzoid

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Re: synthesizing 1-phenylethanol
« Reply #19 on: November 08, 2012, 12:21:08 PM »
So you could start by alkylating with either friedel crafts acylation (reduce) or alkylation. Then Brominate the benzylic carbon with NBS and uv light. Next do an elimination with sodium tert-butoxide to get the double bond. This molecule(styrene) can now be reacted with B2H6, H2O2, and NaOH to give the anti-markovnikov product which is 2-phenylethanol. If you want 1-phenylethanol just use H2O, H+ instead of B2H6, H2O2, and NaOH.

Hope this helps!

Offline Steenrod

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Re: synthesizing 1-phenylethanol
« Reply #20 on: November 08, 2012, 12:23:34 PM »
Thanks for your answers, all of you! :)
I am horrible at chemistry.I am always liable to fail my chemistry exams.So, sorry for stupid questions.

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