Organic chemistry is a branch of chemistry that deals with organic molecules. Organic molecules generally have C-H or C-C bonds.

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D/L Configuration

Why are D and L-glucose enantiomers???! I thought D/L refers to the "configuration" of the last chiral carbon on the open chain Fischer projection. In the D form, the higher priority group is on the ...
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Are all anomers diastereomers?

I am told that all anomers are diastereomers. I think this is BS. If there is a carbohydrate with only one chiral center, then changing the configuration of the anomeric carbon gives us enantiomers. ...
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Phenol protection

Would an acceptable way to protect a phenolic alcohol be through a Williamson ether synthesis? As in: 1) Deprotonating phenol with sodium hydroxide. 2) Addition of methyl iodide. 3) Deprotection ...
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Airbags have become a standard safety feature in modern automobiles. [on hold]

Airbags have become a standard safety feature in modern automobiles. Several airbags are placed in the critical locations within automobiles and they inflate almost instantly upon impact to protect ...
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1answer
45 views

Reduction of acetaldehyde from rectus and sinister faces

I am asked to consider the reduction of acetaldehyde from the re and si faces. I am also asked whether the added hydrogen (labeled H* in my picture) is pro-R or pro-S in both cases. In my attached ...
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29 views

Bond Dissociation Temperatures for Hydrocarbons

I'd like to know the temperatures that various hydrocarbons such as methane, butane, and propane, etc. will dissociate into hydrogen and carbon. Is there a reference where I can look up these ...
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54 views

How to draw glucose using a Fischer projection?

I asked how to draw glucose as a Fischer projection from its given chair conformation but all I got was an unsatisfactory ad hoc explanation involving rotation of my neck muscles to somehow see where ...
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105 views

Acidic conditions, high heat, and return to carboxylic acids

Apparently carboxylic acid derivatives such as cyanohydrins can be taken back to "daddy" - a carboxylic acid - under the right conditions. This involves acid, water, and "high heat." What, however, is ...
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43 views

Convert Hexane to 1,6-Dibromohexane

Is it possible by any means or by using some reagents to convert Hexane to 1,6-Dibromohexane Hexane: 1,6-Dibromehexane: The yield should also be good
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347 views

Interpreting a Formula Tattoo (Bipolar?)

Found This Online. Something to do with bipolar disorder?
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Anti hydrogenation of alkynes-Purpose of NH4Cl

In my orgo textbook, Lithium is used to create a free radical of the alkynes, to then allow the anti addition of hydrogen to get an alkene. "The Dissolving Metal Reduction of Alkynes" is a reaction ...
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74 views

Why does silicon not react with O2?

I'm doing a organic lab, I'm heating up Silicon, Carbon, and sulfur individually then placing them in pure $\ce{O2}$. So I don't really know about carbon chemistry but I thought the reaction might be ...
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39 views

How do Gilman reagents open epoxides?

From what it looks like, Gilman reagents are good nucleophiles, and will attack at the less-substituted side of an asymmetric alkane because Gilman reagents don't necessarily need a substantial ...
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15 views

Hydrolysis of cyclic acetal

What happens to this cyclic acetal when it is hydrolyzed under acidic conditions? I know that under acidic conditions the first thing to likely happen is protonation. Does it matter which oxygen ...
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56 views

Is cyclobutadiene anti-aromatic?

Cyclobutadiene is very unstable. But, some sources claim that this instability can be attributed to other factors such as ring and angle strain rather than antiaromaticity. Cyclobutadiene is simply ...
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Mechanism for hydroxyethylation on nucleobases (e.g. Thymine)

I'm trying to figure out the following reaction mechanism There's a reference paper by Yanagi and Akiyoshi(1959) showing the hydroxyethylation of imides resulting in the following I have two ...
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1answer
33 views

What are some of the simplest chiral molecules in biological systems

I have understood generally for a while there is a significant preference in "life" for so-called "left-handed" (chiral) molecules, though I'm reading things now that say "life" sugars are ...
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20 views

Software for predict physical and chemical properties [closed]

Are there something soft for predicting properties (except for Openbabel)?
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417 views

Are carbocations that bad?

My professor has an anti-fetish for carbocations. In any mechanism that we draw with a carbocation, the maximum earnable credit is automatically halved. In any case, he draws all mechanisms involving ...
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63 views

Why doesn't the Brady's test (2,4-DNPH) work on carboxylic acids?

Why does the Brady's test, the reaction of 2,4-dinitrophenylhydrazine with aldehydes and ketones, fail with carboxylic acids?
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Hydrolysis of Dimethyl dichlorosilane

Dimethyl dichlorosilane will undergo hydrolysis to form siloxane polymers. But why would its carbon analog Dimethyl dichlorocarbon not be able to undergo a similar hydrolysis reaction to form ...
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1answer
37 views

Oxidation of toluene to benzoic acid in presence of KMnO4

Why alkaline $\ce{KMnO4}$ is used in oxidation of toluene to benzoic acid ? What is the reason ? Can acidified or neutral $\ce{KMnO4}$ be used in this conversion ?
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29 views

Effect of temperature on benzenediazonium

What will benezendiazonium ion become if it is not maintained at temperature below 5 degree celsius during diazotization?
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22 views

Why does Cl- get eliminated from a trichloromethyl anion to give dichlorocarbene? [closed]

In the formation of dichlorocarbene, sodium trochloroacetate (in tetrachloroethene) is refluxed at 130 deg C resulting in decarboxylation which forms a trichloromethyl anion. (Does this step happen ...
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36 views

Si and Re facial descriptors

I am considering the hydrogenation of 2-butanone with respect to its Re and Si faces. So if we look at 2-butanone as I've drawn below from above we are looking at its rectus face. And from below we ...
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53 views

Is there a hierarchy to functional groups?

I think I am getting slightly confused about the names we give to functional groups. I am aware that there are different types of functional groups such as alkyl, aryl and acyl groups. I also know ...
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152 views

Why can't carbon form an ionic bond?

My textbook says that a $\ce{C^{4+}}$ cation cannot be formed because it requires a lot of energy to remove 4 electrons. Formation of ionic bonds involve "removing" electrons and there seems to be ...
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46 views

Are all esterification reactions reversible? What is their general mechanism?

For example the reaction of ethanoic acid with ethanol is reversible, however is this true for all esters? I'm not quite whether it is as easy for a reversible reaction to occur both ways. Is there a ...
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What are the product(s) of red phosphorous when burned?

A match box lighter strip typically consists of powdered glass and red phosphorous. When this part is burned, it's residue is like a sticky dust that, when applying friction, will release smoke or ...
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Why doesn't this structure represent a substituted pentane?

In the following ASCI structure (single bond under "$\ce{CH}$" containing $\ce{CH2,CH2, CH3}$) $$ \begin{align*} \ce{CH3-CH2-CH2-&CH-CH3}\\ &|\\ \ce{&CH2-CH2-CH3} \end{align*} $$ The ...
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23 views

Regioselectivity of Nitrosation of Phenol

When phenol reacts with nitrous acid ($\ce{NaNO2 + \mathrm{conc}\ H2SO4}$), 4-nitrosophenol and not 2-nitrosophenol is formed. I cannot understand why the p- isomer should be preferred over the o- ...
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24 views

Effect of valence electrons on an atom's electronegativity

I had a question about carbon atom specifically, carbon have 4 valence electrons, with electronegativity of 2.55(approximation), now if I was to fire electrons at the carbon atom, each carbon will ...
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1answer
39 views

Why is C4 of butynone electrophilic?

A question asks whether C4 in 3-butyne-2-one can act as a nucleophile, electrophile, or acid (it can be more than one). The answer is that it can be both electrophilic and acidic. The acidity makes ...
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42 views

Can butan-2,2,3,3-tetraol be oxidized by Potassium permanganate?

Can the compound butan-2,2,3,3-tetraol, $\ce {C4H_6O4} $, be oxidized by $\ce{KMnO_4}$? If so, in what conditions? As I have learnt in class, normally the hydroxy group would oxidize to form a ketone, ...
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What functional groups are subsets of the Alkoxy group?

In a quiz, I was asked to find all of the combinations of organic molecule of $\ce{C4H6O2}$. The combination excludes -COOH, -OH, double bonds and the alkoxy group. The only problem, as far as I am ...
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Grignard reagent vs Gilman reagent

As far as I know, in order to synthesize a hydrocarbon $\ce{R-R'}$, Grignard reagent or Gilman reagent could be used. $\ce{RMgX + R'X -> RR' + MgX2}$ $\ce{R2CuLi + R'X -> RR' + LiX + RCu} $ ...
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Oxidation of formate ion by peroxydisulfate in water solution: Why are there “strange” kinetics?

As you can see, the first step is the slowest, but by using the rate-determining step approximation you wouldn't arrive at the correct rate law which is: $\ce{r=k[HCOO^{−}]^1^/^2 [S2O8^{2−}]}$. ...
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Complicated reaction mechanism

The reaction is this: The only idea I have thus far is if we have a chloride acid that can form an ester, then we might be able to find a suitable mechanism. This would require a chloride reagent.
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Electrophilic addition of HX to 2,3-dimethylbut-2-ene

Generally, for the addition of dry HX to an alkene, it follows Markovnikov's rule. The hydrogen atom adds to the carbon with the most hydrogen atoms. However, in the case of an alkene which does not ...
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Type of hybridisation

State the hybridisation of asterisked carbon in $\ce{CH3 - CH = C^{✪} = CH2}$ I am not sure between $sp^2$ and $sp$ hybridization. Because of double bond I think it should be $sp^2$ but because of 2 ...
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137 views

Proton NMR signals and rings

Does pyridine or furan have the more shielded proton NMR signals? I know that both are aromatic, so both have rather deshielded signals due to ring current combining constructively with the applied ...
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51 views

What is the liquid in Mathmos lava lamps?

How can I identify the liquid in Mathmos lava lamps? I have two of them with broken caps, I need to get rid of them. Can I flush the stuff down the toilet? It smells funny.
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How does sugammadex (a modified cyclodextrin) draw rocuronium into its lipophilic cavity?

Sugammadex is a modified cyclodextrin: 8 member sugar ring with carboxyl thioether extensions. Rocuronium is an aminosteroid, 4 steroid rings and one protonated amine group. Sugammadex binds ...
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Formation of halohydrin vs alkyl dihalide

For the electrophilic addition of $\ce{X2}$ to alkene in $\ce{CCl4}$ solvent, a dihaloalkane is formed. This is a halogen addition reaction, with the intermediate being a halonium ion. However, if ...
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162 views

Why is a strong base needed for an E2 reaction and not a an E1 reaction?

For E2 reactions, why is a strong base like NaOH or RONa needed? Whereas for E1, even a weak base like H2O could be used. Wikipedia states: E2 typically uses a strong base, it needs a chemical ...
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32 views

Conditions for making amines from halogenoalkanes?

From what I understand, to make an amine from a halogenoalkane you need to heat the halogenoalkane with a mixture of ammonia and ethanol. I just had a few quick questions: Do both the ammonia and ...
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79 views

Can functional groups exist by themselves

Just started to study organic compounds and I am curious about functional groups. I want to know if functional groups can exist as molecules themselves.
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13C NMR peak location in butanone

The above is the correct $ ^{13}C $ NMR spectrum of butanone. In the $ ^{13}C $ NMR spectrum of butanone, I figure that the peak locations of the first and third carbons should be switched (27.3, ...
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giving a conclusion from observation

There is a question I come across of an examination. I know the answer and also know the solution. Well when I first saw this problem I don't know how to approach this problem and I think I will ...
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Dextro,Levo rotatory and D/L Configuration

What does D(-) tartaric acid mean? D is always (+) Glyceraldehyde, therefore it should be +? If I am not wrong, the D indicates (+) Glyceraldehyde and L indicates (-) Glyceraldehyde and the (+) and ...