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Author: Subject: typo in Vogel?
bigdaddymac
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[*] posted on 13-12-2015 at 08:31
typo in Vogel?


Hello. This is the first time I have posted a question to the forum, even though I am a long time reader. This is mainly because I like to try to search and solve problems for myself before posting a question, but this one has me stumped:

In Vogel's "Practical Organic Chemistry", 5th Ed, pp. 1035-1036, it states:

3,4-Methylenedioxy-β-nitrostyrene

In a 250-ml round-bottomed flask mix 30g (0.20 mol) of 3,4-methylenedioxybenzaldehyde (piperonal), 13.4 g (0.22 mol) of nitromethane, 7.8 g (0.1 mol) of ammonium acetate and 50 ml of glacial acid. Attach a reflux condenser, and boil the mixture under gentle reflux for 1 hour. Pour the reaction mixture with stirring into a large excess of ice-water (about 1 litre). When all the ice has melted, filter off the crude product under suction and recrystallise from a mixture of absolute ethanol and acetone (about 2:1 v/v). Almost pure yellow crystals of the nitrostyrene, mp 161°C, are obtained. The yield is 23.3 g (60%). Further recrystallisation from the same solvent yields the pure compound, mp 162°C.

Shouldn't this be 'nitroethane'?

I understand that this topic of enquiry could be construed as 'drug chemistry', however I have no interest in that domain whatsoever. I'm just wondering if it is a typo.
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unionised
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[*] posted on 13-12-2015 at 08:52


The mass and number of moles
13.4 g (0.22 mol)
don't tally for nitroethane, but they do for nitroMethane.

And the number of carbons in that bit of the molecule (hanging off the ring) works with one from nitromethane and one from the aldehyde group giving two in the styrene derivative.
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Sulaiman
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[*] posted on 13-12-2015 at 09:33


bigdaddymac, anyone who spotted/encountered such a mistake should not be just 'lurking'
there are plenty of less experienced members like myself who need all the help/guidance/support that we can get,
stop lurking and help us please, pretty please ?
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UC235
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[*] posted on 13-12-2015 at 09:39


It's not a typo, because Vogel isn't giving you a recipe for 3,4-methylenedioxyamphetamine precursor. If you'd bother to draw the reactants and products, you'll find that nitromethane will indeed produce the β-nitrostyrene as advertised.
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aga
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[*] posted on 13-12-2015 at 11:42


Even after 20 cans i'd have looked at this very hard indeed before questioning Vogel.



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bigdaddymac
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[*] posted on 13-12-2015 at 11:49


ahh ok thank you for your responses. So to clarify, nitroethane and nitromethane produce different nitrostyrenes.

According to UC235, the use of nitroethane produces an amphetamine precursor; and the use of nitromethane produces something different entirely (I'm curious as to what, actually). This makes sense because I'm sure that Vogel, like myself, was not a drug chemist aficionado.
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[*] posted on 13-12-2015 at 12:31


Work it out for yourself.

Post your results and workings out and folks like UC235 could check it for errors.

I could check it for mistakes with the colouring-in, smudges etc.




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[*] posted on 2-3-2020 at 17:54


I found an error on page 892, preparation of aniline, and on page 562 of the 3e the error is not present. Didn't think it would be worth having an older version! Before cross-referencing the 3e, I searched for 'Vogel typo' and found this post. Thanks for the great laugh.
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