Questions tagged [organic-chemistry]

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.

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26 votes
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What makes diazo compounds so unstable and explosive?

I once had an Orgo TA refer to a diazo compound as "diazo-boom-boom" (the technical term). I have always been curious as to the reason behind the instability and reactivity. According to Wikipedia ...
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12 votes
3 answers
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How can we synthesize para-nitrophenol

During nitration of phenol, both para- and ortho-nitrophenols will be formed. Is there any way in which we can synthesize para-nitrophenol only?
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13 votes
2 answers
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Why is benzyne an intermediate?

I've always seen benzyne (benzene with a triple bond) classified as an "intermediate". I really don't see why it needs to be an intermediate, though. The possible reasons I can come up with are flimsy:...
23 votes
3 answers
7k views

What makes an epoxide stable?

Overall ring strain seems to be a big issue when it comes to organic chemistry. That is why cyclopentane may be in an "envelope form" or why cyclobutane may be in a kinked, kite form. Both of these ...
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9 votes
1 answer
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Why is it that the bigger the side-chain is, its hydrogen atoms tend to be more equatorial?

The most stable cyclohexane form is the chair conformation but on the other hand, the bigger the side-chain of the cyclohexane is, its hydrogen atoms become more equatorial rather than axial, which ...
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29 votes
3 answers
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How do you separate enantiomers?

There are some stereochemical reactions that result in the presence of enantiomers. When moving forward with a practical organic synthesis, how does one usually separate them in order to continue with ...
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19 votes
3 answers
1k views

Why are arenes with conjoined benzene rings drawn as they are?

Whilst we are taught to represent benzene as below (A) due to its delocalised electrons, however when two benzene rings share carbons (e.g. naphtalene) it seems to be more commonly represented in ...
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18 votes
2 answers
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How large is the energy difference between keto- and enol-form of guanine and uracil?

The nucleobases in DNA and RNA are generally present in the keto-form, and not in the enol-form. As an interesting historical note, James Watson and Francis Crick did initially believe them to adopt ...
20 votes
4 answers
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During the development of aspartame, why was the methyl ester chosen?

One frequent argument against the safety of the synthetic sweetener aspartame is that it can be hydrolyzed, with one of the hydrolysis products being methanol, which is known to be toxic. Of course, ...
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48 votes
1 answer
29k views

Mechanism of arene side chain oxidation by permanganate

When treated with hot, concentrated acidic $\ce{KMnO4}$, arenes are oxidised to the corresponding carboxylic acids. For example, toluene is oxidised to benzoic acid. I've tried to examine how this ...
25 votes
3 answers
2k views

What can I do if I don't get a phase separation between my organic and water phases?

Solvent extraction in a separation funnel is a very common method in preparative organic chemistry. But sometimes you don't get a nice phase separation between the organic and the water phase. What ...
14 votes
1 answer
406 views

How does the choice of metal (oxide) catalyst affect the range of unsaturated compounds that can be hydrogenated?

In the hydrogenation of unsaturated compounds with hydrogen gas and a catalyst, the choice of palladium on carbon is able to hydrogenate alkenes and alkynes, but is unable to hydrogenate aromatic ...
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15 votes
1 answer
5k views

Acid catalysed synthesis of ethyl ethoxymethylenemalonate

One synthesis of quinolones begins with the formation of an ethyl ethoxymethylenemalonate, as seen in this Organic Syntheses paper. I've been asked if the malonate derivative would be formed if ...
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25 votes
2 answers
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Michael reaction or nucleophilic attack at the alpha carbon of an alpha-beta-unsaturated ketone?

What conditions promote a nucleophile to undergo the Michael reaction over the nucleophilic attack at the alpha carbon of the carbonyl group in an alpha-beta-unsaturated ketone? I'm looking for an ...
15 votes
2 answers
484 views

Can recent developments improve the total synthesis of B-12?

The total synthesis of vitamin B-12 by Robert Burns Woodward and Albert Eschenmoser, is over 30 years old. At its time, it was considered a landmark in the field. With current developments (e.g. ...
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21 votes
1 answer
526 views

Precedence of 1,2 carbocation rearrangement

How can one choose which group has more shifting tendency in 1,2 carbocation rearrangement? The obvious order is via the stability of the carbocation of the group. But, phenylic groups have high ...
30 votes
4 answers
10k views

Is activated carbon classified as organic or inorganic?

Organic compounds are typically defined as “molecules containing carbon”. Wikipedia states that there for some historical (read: non-logical) reasons, a few types of carbon-containing compounds ...
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18 votes
1 answer
1k views

Stability of organophosphorous vs organophosphates?

In environmental chemistry, most of the organophosphorous compounds we worry about are actually organophosphate compounds. Is there something about the $\ce{C-P}$ bond that makes it less stable (and ...
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48 votes
2 answers
15k views

Why does nitration of N,N-dimethylaniline occur at the meta position?

The nitration of N,N-dimethylaniline with $\ce{H2SO4}$ and $\ce{HNO3}$ gives mainly the meta product, even though $\ce{-NMe2}$ is an ortho,para-directing group. Why is this so?
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18 votes
1 answer
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How does Polytetrafluoroethylene (Teflon) differ from Polyvinylidene fluoride (PVDF) as a protein binding membrane material?

PTFE and PVDF (durapore) are both used in protein binding filter membranes (Millipore specifically). Chemically speaking the two polymers differ quite significantly due to the additional fluorides and ...
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