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#Post#: 1132--------------------------------------------------
Solve: Organic chem question
DIR By: Michel
Date: November 16, 2012, 1:06 am
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A useful organic compound R(C6H10O) reacts with hydroxylamine
and 2,4-dinitrophenylhydrazine to give crystalline derivatives S
and T. On treatment with iodine and NaOH solution, R forms
iodoform but does not form any silver mirror when treated with
Tollen's reagent. It decolorises a solution of Br2 in CCl4,
forming compound V(C6H10Br2O). Vigorous oxidation of R using
chromic acid gives propanoic acid as one of the products.
Compound R has an isomer W which does not give iodoform but
under similar oxidation yields acetic acid as one of its
products. Show how you interpret all the reactions and suggest
names for R,S,T,V and W
#Post#: 1137--------------------------------------------------
Re: Solve: Organic chem question
DIR By: Michel
Date: November 17, 2012, 4:01 am
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Ne replys?
#Post#: 1160--------------------------------------------------
Re: Solve: Organic chem question
DIR By: Chemist@
Date: November 19, 2012, 7:44 am
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R=hex-3-en-2-one;
S=hex-3-en-2-one oxime;
T=hex-3-en;
V=3,4-dibromo-2-hexanone;
W= maybe hex-2-en-3-one.
Ketone+hydroxylamine=oxime;
Ketone+2,4-dinitrophenylhydrazine=alkane (in this case alkene);
Iodoform reaction=methyl group in the ketone;
Oxidation=cleavage of the double bond, meaning that the ketone
has a CH3CH2CH=group;
Everything combined should give the previously mentioned
compounds.
#Post#: 1162--------------------------------------------------
Re: Solve: Organic chem question
DIR By: Michel
Date: November 19, 2012, 9:32 am
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Correct :)
#Post#: 1163--------------------------------------------------
Re: Solve: Organic chem question
DIR By: Michel
Date: November 19, 2012, 9:44 am
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With 2,4-dinitrophenylhydrazine, you get
hex-3-ene-2,4-dinitrophenylhydrazone
#Post#: 1164--------------------------------------------------
Re: Solve: Organic chem question
DIR By: Michel
Date: November 19, 2012, 9:49 am
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Treating with a strong base can give the 2-phenyl-3-hexene
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