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Results tagged with organic-chemistry
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user 38684
Use this tag for questions relating to organic molecules and their properties (structure of organic molecules, spectroscopic properties, reaction mechanisms, stereochemistry etc). DO NOT use this tag as the only tag in your question, as this tag by itself cannot appropriately classify your question. Always use this tag in addition to other more specific tags.
2
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0
answers
129
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Why is there a need to rotate the molecule in a sharpless asymmetric epoxidation?
As far as I understand sharpless epoxidation, you first need to rotate the molecule such that the vincyclic alcohol is in the upper right quadrant. Then, the epoxide forms on the top/bottom of the dou …
- 1,796
1
vote
0
answers
74
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Why does a Beckmann Rearrangement not occur in the in nitrosation of cyclohexanone?
In my textbook Organic Chemistry, 2nd edition by Clayden, on pg. 464 it states the addition of $\ce{NO2-,HCl}$ to cyclohexanone to 2-nitrosocyclohexanone, which hydrolyses to 1,2-cyclohexadione. Why d …
- 1,796
3
votes
0
answers
1k
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Ring expansion in the reaction of (hydroxymethyl)cyclobutane and HBr [duplicate]
I saw a question on how to predict the product of a reaction between (hydroxymethyl)cyclobutane and HBr. The correct answer was given as 1-bromocyclopentane, however, I do not understand why a ring ex …
- 1,796
2
votes
Accepted
Naming of an organic compound
The substituents go alphabetically, and as 'chloro' is before 'methyl' in the alphabet, the correct name is 2-chloro-4-methylpentane.
- 1,796
7
votes
Why isn't the hydroxyl group of citric acid deprotonated while the carboxyl groups are?
You are correct in saying that the carboxyl groups will have resonance structures after being deprotonated. Thus, the carboxyl groups are fairly acidic and will deprotonate in water. On the other hand …
- 1,796
5
votes
1
answer
6k
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Why do carboxylic acid derivatives show a more upfield shift than carbonyls in 13C-NMR?
The prototypical 13C NMR shifts of carbonyl carbons is in the range 190–200 ppm, however, carboxylic acid derivatives have a 13C NMR shift in the range 160–180 ppm instead. What structural factors cau …
- 1,796
0
votes
4
answers
4k
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Oxidation product of alcohol
What is the oxidation product of a primary alcohol?
(A) aldehyde (B) alkene (C) ester (D) ketone
My try: So because an alcohol is $\ce{R-OH}$, and oxidation is loss of electrons, I thought that the …
- 1,796
6
votes
2
answers
886
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Reduction of 1,4-benzoquinone in the synthesis of 1,5-diazocane
Synthesize 1,5-diazocane using only benzene as a source of
carbon atoms, and ammonia as the only source of nitrogen atoms.
My attempt: Noticing that the target compound has split the benzene ri …
- 1,796
3
votes
0
answers
997
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Why does the proton transfer from the oxygen to the nitrogen atom in imine formation not occ...
In my book Organic Chemistry by David Klein, 2nd edition, the book shows that the oxygen atom first takes a proton from an acid, then, the conjugate base of the acid takes a proton from the nitrogen …
- 1,796
3
votes
1
answer
567
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Organic nomenclature of substituted diamines
Nomenclature of substituted amines is done with the N-locants, with the N being used to indicate that a group is connected to the methyl group. I was wondering, therefore, on how to properly name a su …
- 1,796
5
votes
1
answer
2k
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Why is methyl α-D-glucopyranoside preferentially formed from glucopyranose in acidic methanol?
According to my textbook Organic Chemistry 2e by David Klein, the formation of a glycoside from glucopyranose favors the α form (see picture below).
Why does this happen? Shouldn't the equilibrium fa …
- 1,796
8
votes
1
answer
1k
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Why don't Gringard Reagents react with carbonyls at the alpha position? [duplicate]
According to many texts, the reason why Gringard reagents cannot be used with alcohols is because the Gringard reagent is a strong base, which would deprotonate the alcohol. ($p\pu{K}_b$ of Gringard $ …
- 1,796
2
votes
0
answers
83
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Nitration of (E)-4-Phenyl-3-buten-2-one
What would happen if (E)-4-Phenyl-3-buten-2-one, shown above is nitrated, and is this compound more or less reactive than benzene?
My Attempt: By drawing the resonance structures of the above compo …
- 1,796
6
votes
0
answers
599
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Why does the keto tautomer of guanine have lower energy?
Looking at the keto and enol forms of guanine, it would seem as if the enol form is more stable, due to the fact that aromaticity is established with the enol form. However, according to a question …
- 1,796