Tagged Questions

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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127 views

why is an ester more acidic than a ketone?

Every book i've read says- esters are more acidic than ketones because the resonance between the two oxygen atoms gives less opportunity for the delocalization of the electron pair on the alpha carbon ...
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2answers
85 views

Reductive amination of (protected) 3-Oxopropanenitrile: Will azetidin-2-ol be formed via intramolecular ring closure?

What happens during this reductive amination? I got the first product; the lithium aluminium hydride will reduce the nitrile to an amine. But what about the reductive animation step? As far as I can ...
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0answers
21 views

What are all isomers of alkenes excluding cyclo? [on hold]

could someone please give me a list of all isomers of alkenes from C1 to C7 excluding stereoisomers and cycloisomers?
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20 views

what is the # of protons on adjacent atoms? what is consider adjacent? [on hold]

looking at the nmr for aspirin, would i consider CH3 as 3 protons adjacent to the aryl hydrogen a couple of carbons away?
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0answers
12 views

about stereochemistry/major product [on hold]

Supply the correct major product formed from the following reaction link to the reaction/picture - http://i.imgur.com/9tmrS38.png
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1answer
32 views

Osmium tetroxide and meta-chloroperoxybenzoic acid

Can these be used to induce acetal ring closures? For example, when dealing with a molecule that has both a C=O functional group and an alkene as part of its structure and there is the possibility of ...
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0answers
19 views

Imine stability in acids and bases

I understand that imines can be hydrolyzed in acidic medium. But what about in basic medium? Can imines still be hydrolyzed? I have a plausible mechanism ... nitrogen's withdrawal of electron ...
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0answers
17 views

Determination of acid contents in sour fruits project? [on hold]

Determination of acid contents in sour fruits project? Any idea about it or any references.
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1answer
20 views

Potassium permanganate oxidation of sugars

I am told that all three sugars below can be oxidized to their corresponding carboxylic acids using potassium permanganate. This strikes me as bloody wrong because only hemiacetal sugars ...
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1answer
20 views

Enolizablity of pyruvate and lactate

I understand that to create an enol, you simply eliminate a proton alpha to the relevant $\ce{C=O}$ and then tack the proton onto the O and there you have it - an alkene and an alcohol - or enol. ...
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0answers
26 views

Positive and negative charges and acidic or basic media

I am told that we shouldn't have any negative charges when showing a mechanism of something that occurs in basic media. The opposite goes for a mechanism occurring in acidic media. Are there any ...
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2answers
49 views

Which is the more stable enol form?

If I understand correctly, when we go from a keto to an enol form, we simply abstract an alpha proton and thereby create a double bond to a carbon bearing the hydroxyl functional group. When ...
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39 views

Sodium cyanoborohydride and iminium reductions

I understand that the LAH will reduce the nitrile into a primary amine. The addition of acid will likely destroy the acetal mask and leave us with ethylene glycol and a molecule with both a ketone ...
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1answer
24 views

Synthesis; effect of hydrogen gas and platinium

I'm pretty sure the last step in there is just something to throw us off. From what I understand, the first step will give us a Grignard, which will attack the carbonyl in formaldehyde to give us a ...
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2answers
92 views

Grignards do transmetallation?

Prof told me Grignards don't add to alkyl halides to create linear carbon extensions because Grignards do transmetallation rather than SN2 displacement of halide. Is this correct? I thought ...
2
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1answer
62 views

Why does graphite conduct electricity?

The answer i know is delocalized electrons. But how?this site tells me that: My textbook tells me that one carbon atom is bonded to three others and two of these bonds are single while the third is ...
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1answer
302 views

What makes carbon special and versatile?

My teacher told me that carbon's tetravalency and high catenation ability makes it special and is the reason why there are millions of compounds of carbon. 1) Silicon is tetravalent too but doesn't ...
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1answer
34 views

Acidic nature of benzene and other alkenes

Is benzene acidic? It has $sp^2$ hybridization so doen it mean that it is acidic in nature? Are alkenes acidic?
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1answer
53 views

What is the mechanism for demercuration?

The following image is from 'Organic Chemistry Second Edition' by Clayden, Greeves, and Warren. The final step is the demercuration, but I'm unable to find a definitive mechanism. The wikipedia ...
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1answer
29 views

Rate Expression for Reactions Involving 2° Benzylic Alkyl Halides

My teacher took off marks because he said the reaction was SN1. Before I go confront him, please tell me if my reasoning is correct. So, basically, I thought: we have two possibilities: 1. SN1: a ...
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22 views

What is the better nucleophile, Cl- or NH3? [closed]

How do you decide? I can't seem to think of any method rather than checking experimental values.
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1answer
26 views

NH2- and Primary Alkyl Halides: Sn2 vs E2

When we mix 1-bromopropane and $\ce{NaNH2}$, what happens? Which reactions wins out to make the major product? My textbook says that primary alkyl halides give mainly SN2 products unless the base is ...
2
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1answer
41 views

Abstraction of a proton in cycloheptatriene

So, whenever there is abstraction of H+ by an acid-base reaction, I see that the proton on the sp3-hybridized carbon is taken. Why is this if you take into account that vinylic hydrogens are more ...
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1answer
33 views

Grignards and diatomic halogens

Can Grignards react with diatomic halogens as to perform an substitution reaction? I'd imagine that the first part of making the reaction work - polarizing the halogen as to prepare to pull it apart ...
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3answers
694 views

Why isn't organic chemistry taught in 3D? [closed]

As the title says. What's the point of learning everything in 2D and trying to visualize and interpret stereochemistry, newman structures, isomers etc, with hundreds of hours wasted, when a 3d ...
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2answers
61 views

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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2answers
173 views

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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1answer
41 views

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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79 views

Airbags have become a standard safety feature in modern automobiles. [closed]

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
60 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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1answer
35 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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1answer
57 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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1answer
111 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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1answer
47 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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1answer
354 views

Interpreting a Formula Tattoo (Bipolar?)

Found This Online. Something to do with bipolar disorder?
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32 views

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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3answers
79 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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1answer
46 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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1answer
19 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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1answer
67 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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2answers
57 views

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
34 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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2answers
423 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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2answers
77 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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2answers
37 views

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 ...
3
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1answer
60 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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1answer
30 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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0answers
25 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 ...
2
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1answer
47 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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1answer
61 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 ...