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

learn more… | top users | synonyms

2
votes
1answer
35 views

What are the resonance structures of 3-aminocyclohex-2-en-1-ylium?

How would you draw the resonance structure for the compound below: This is one of the resonance forms I think... but I'm sure there is another one too.
3
votes
2answers
182 views

Can dimethylmercury originate from cleaning up a broken thermometer with disposable wet wipes?

I broke a CFL in my home (so elemental mercury is present in a small amount) and wiped up some of the mess with a clorox wipe. The wipe in question contains dimethyl benzyl ammonium chloride and ...
5
votes
2answers
41 views

How to determine bond length and angle in a conjugated pi-system (polymethine)?

I have a polymethine molecule with let's say 9 $\ce{C}$ atoms. $\ce{H-CH=CH-CH=CH-CH=CH-CH=CH-CH3}$ How can I calculate the length of the whole molecule? I need this number to compute the ...
2
votes
1answer
29 views

Can pseudochirality be considered when 3 or 4 groups on the C atom are the same?

When for example the C atom is bonded to one H, and then three more structurally identical groups with 2 chiral C each - in configurations R,R and S,S and R,S respectively - then by assigning each of ...
7
votes
1answer
776 views

What is the significance of 273.16 K?

Today, at my chemistry class, we were learning how to convert Celsius to Kelvin with exact values. I said we add 273.15 K to given Celsius but my colleague said we add 273.16 K. Yes, I did check on ...
7
votes
1answer
53 views

Mechanism for acid-catalyzed dehydration of 2,3-dimethylcyclopentanol

How do you get from 2,3-dimethylcyclopentanol to 1,2-dimethylcyclopent-1-ene? I know the -OH group leaves as water (being protonated by acid) forming a carbocation. Then the weak nucleophile (water) ...
3
votes
2answers
68 views

Origin of alkenes from Wurtz Reaction

According to Wikipedia: Also, since the reaction involves free radical species, a side reaction occurs to produce an alkene. This side-reaction becomes more significant when the alkyl halides are ...
2
votes
0answers
15 views

Does Wurtz reaction follow an ionic mechanism or a free radical mechanism?

In Wurtz reaction, is the intermediate formed a carbanion or a free radical. And if can assume both mechanisms to be true, how can we decide the reacitivity of a tertiary halide?
4
votes
1answer
38 views

Which carbocation is more stable , the one attached to methyl or the one attached to ethyl?

$\ce{C2H5+ vs \ C3H7+}$ There are two conflicting trends here. Inductive effect of ethyl will be higher than that of methyl so carbocation attached to ethyl ( 3 carbons in total) should be more ...
9
votes
1answer
139 views

Experimental verification of the field effect

March's Advanced Organic Chemistry has the following paragraph - The other effect operates not through bonds, but directly through space or solvent molecules, and is called the field effect. ...
5
votes
1answer
44 views

Viewing a protein or bio structure in Chembio3D in its natural conformation

I notice when using SMILES or a IUPAC name for many molecules and generating them in Chembio3D, and then running MM2 > Minimize Energy, the structures produced are most of the time not reflections of ...
3
votes
2answers
33 views

Why is a hydrocarbon tail non-polar?

Here it says that the hydrocarbon tail is non-polar. I understand that the $\ce{H}$ on top of the $\ce{C}$ and on the bottom have dipoles that cancel, but at the very end, with the $\ce{CH3}$ group, ...
1
vote
1answer
25 views

Equivalent hydrogens in 2,3-dimethylbutane

So while calculating for the relative yield of monochlorination for 2,3-dimethylbutane, I was counting the primary hydrogens, I counted 6, but in fact it was 12. Why is it 12? How do you find ...
0
votes
0answers
18 views

Boiling point and melting point of dihalobenzene compounds [duplicate]

In Dichlorobenzene what explains the boiling and melting point of the 3 structures that can be formed? According to Google The melting point decreases in the order- Para>Ortho>Meta And Boiling ...
2
votes
1answer
29 views

Ortho para meta stability

When is the para form of a compound more stable than the ortho form? Similarly when is the meta form more stable? I know that for +I effect ortho para are major products and meta for - I effect. ...
2
votes
1answer
30 views

Carbocation Rearrangement Due To Ring Strain And Back Bonding

Today our teacher told us that the following carbocation rearrangement occurs due to back bonding.I could not really follow what he meant.Can someone please explain what is actually happening during ...
1
vote
1answer
20 views

Does intramolecular hydrogen bonding occur in dicarboxylic acids?

Consider ethanedioic acid: Could it form intramolecular hydrogen bonds (between the C=O and HO)?
8
votes
3answers
470 views

How can I easily explain to a layperson the difference between types of “contains”

I had a conversation with somebody who had somewhat confused ideas about food. He thought that "all food contains sugar" and when I gave a bottle of oil as the counterexample, he said the glycerol is ...
4
votes
1answer
38 views

Why is glycine hydrochloride more acidic than chloroacetic acid?

I cannot figure out why glycine hydrochloride is more acidic than chloroacetic acid. Could I have figured this out from a pKa table and maybe am just not seeing it? On the table I have in my book ...
4
votes
1answer
40 views

Factors affecting fluorescence in organic molecules

Rhodamine is a fluorescent dye. What features of the molecule result in it being so highly fluorescent ? I assume the extended conjugated system with a stabilized first excited state is necessary, ...
5
votes
1answer
151 views

Determining Aromaticity?

Could someone help me determining the aromaticity of the compounds? My Attempt: (i) not an aromatic compound since it only has 4 pi electrons that does not satisfy Huckels (4n+2) rule (ii) not ...
0
votes
0answers
24 views

a chemical model for pde

Consider the initial boundary value problem $$u_t=a(t)u_{xx},\,\,\,0<x<1,\,\,\,t>0$$ $$-ku_x(0,t)=hu(0,t),\,\,\,t>0$$ $$u(1,t)=u_0,\,\,\,t>0$$ $$u(x,0)=f(x),\,\,\,t>0$$ where ...
2
votes
2answers
50 views

Stereochemical aspect of heating of cyclohexane-1,2-diol

Does stereochemistry play any role in the heating of Cyclohexane-1,2-diol? If I remember correctly, different products are formed depending on whether the diol is cis or trans. (I think the products ...
5
votes
1answer
55 views

Mechanism for formation of amide by reaction of amine with ester

This is the mechanism given in my lecture handout: I have a problem with the third species along. Surely the negatively charged oxygen would protonate before the other oxygen would. Also, why does ...
5
votes
2answers
133 views

Why do we insert a numerical multiplier after group positions when naming an isomer?

For example, take 2,3 dimethylbutane for example. Why do we add the numerical multiplier 'di' when we've explicitly mentioned two locations? Why not just use 2,3 methylbutane? It seems highly ...
6
votes
2answers
66 views

Addition of HBr to Vinyl bromide

The addition of $\ce{HBr}$ to $\ce{CH2=CHBr}$ produces $\ce{CH3-CHBr2}$. Why is this so? According to me, halogens have a stronger $-I$ effect than a $+M$ effect (for example a halogen substituent on ...
0
votes
2answers
34 views

Are ethyl iodophenylundecylate and Ethyl-10-(Iodophenylundecanoate) the same compound?

I have no understanding of chemistry, so these to chemical formulas mean nothing to me. What I am trying to ascertain is are these compounds the same? If not, what differences are there especially if ...
2
votes
1answer
44 views

Understanding the hybridization of cyclohexane?

I'm having quite a fair bit of trouble comprehending the hybridization of cyclohexane. I understand that this is a ringed structure with single C-C bonds, therefore all the carbons should have sp3 ...
0
votes
0answers
24 views

Is it possible to form cyclohexane by oxidizing an alcohol? [closed]

Is it possible to form cyclohexane by oxidizing an alcohol? I believe not but I'm not sure.
5
votes
1answer
48 views

Clemmensen reduction of 1,3 diketones

As part of a synthesis I was considering the following reaction: How selective is the Clemmensen reduction? I know that the Clemmensen reduction favours ketones adjacent to benzene rings but will ...
3
votes
3answers
54 views

Why do we use ethanol in SN2 reaction?

Solomons and Fryhle has an example in which they have showed a very simple substitution reaction. The question was to synthesize methyl iodide. What they have done is taken methyl chloride and ...
4
votes
1answer
49 views

Amide synthesis SM alkylchloride

In this question immediate reaction is to make a grignard reagent with B by reacting it with magnesium and have it attack $\ce{COX(N(Me)2)}$ to form $\ce{C}$ Im not sure how it would be possible to ...
0
votes
0answers
15 views

Charged nucleophile and SN1/E1/SN2/E2 reactions

How can we say that if a charged nucleophile/base is present we can safely rule out the possibility that the reaction can take place via SN1/E1 mechanism? I have been trying to figure this out since ...
3
votes
1answer
84 views

Alkylation of alkenes by nucleophilic substitution

A double bond/alkene reacts as a nucleophile. I have never seen a reaction where it takes part in an $S_N1$ or $S_N2$ reaction with a halogenoalkane for example. This would presumably be a very useful ...
8
votes
1answer
36 views

Naproxene syntheses: electrophilic aromatic substitution on activated naphthalene

I am studying Syntex's naproxene syntheses and I came across a couple of electrophilic substitutions whose mechanism I can't understand. The first one is a Friedel-Crafts acylation: the products are ...
-2
votes
0answers
34 views

Glucose and Phenylalanine, which one is planar and which non-planar? [closed]

I'm having trouble understanding how to decipher it, and have been googling and not got very far. thanks for your help
4
votes
1answer
19 views

Determine how many gauche interactions?

The textbook states that a) has 2 gauche interactions, b) has 3 gauche interactions and c) has 3 interactions But how do we determine this? I thought a gauche interaction would occur when two ...
1
vote
1answer
15 views

Solvents in substitution reactions

My book says that to favour a reaction by SN1 mechanism we need to use a polar protic solvent and a polar aprotic solvent in a reaction by SN2. * My Prior Knowledge:* There are two types of polar ...
4
votes
1answer
31 views

Fluorination with xenon difluoride

Is this an error? Why is the nitro group reduced as the benzene ring is oxidized? I don't see any possible reducing agents here.. Also, what is the mechanism of aromatic fluorination by xenon ...
0
votes
1answer
37 views

Phenyl or benzene when naming compounds

In this picture, the last two molecules are both rings. However, the second last molecule has a halogen substituent and was named "bromobenzene". The last molecule had a chlorine and a hydroxyl ...
-3
votes
0answers
17 views

How many molecules are contained in 1058 grams of lead (IV) nitrate? [closed]

Include units. But do not write chemical formula.
0
votes
1answer
19 views

What is the byproduct from hydrogenolysis of an acyl chloride?

What's the byproduct of this reaction? After all, it is a "lysis" reaction. So ... would HCl be a byproduct?
2
votes
1answer
52 views

Can carboxylic acids be used in the aldol reaction?

A question in a practice paper I did recently showed the aldol condensation of benzaldehyde with ethanoic acid. I think I am right in saying that carboxylic acids do not form enolates because the ...
1
vote
1answer
19 views

Is the correct configuration assigned to the given pair of geometrical isomers?

I suppose that the configurations assigned are opposite as in the left isomer, the left chlorine atom is coming out of the plane of the paper while the other is going into the plane of paper. So it ...
0
votes
0answers
18 views

Taxus baccata- alcoholic bevarage [closed]

I came here with a simple question; that is: Is it possible to make an alcoholic bevarage from Taxus Baccata?
5
votes
1answer
47 views

Why is i-butane more stable than n-butane?

I would like to understand the term stability in organic chemistry. We know empirically that i-butane is more stable than n-butane. But why is it more stable? Is it because of formation enthalpies or ...
3
votes
1answer
32 views

Oxymercuration Demercuration Mechanism doubt

I'm having a doubt on the mechanism of oxymercuration Demercuration reaction. How does the reaction, initially heading towards anti addition(after cyclic transition state formation) ,get spoiled by ...
3
votes
1answer
30 views

Mechanism of enolether formation with ethyl orthoformate in estr-4-ene-3,17-dione (Djerassi's norethisterone synthesis)

The second step of Djerassi's synthesis of 19-nor-17α-ethynyltestosterone (norethindrone), involves the protection of the ketone in position 3 via enolether formation, as in the picture: What is ...
2
votes
1answer
49 views

What happens to chemical shifts of protons close to aromatic systems in ¹H-NMR?

I have two questions regarding chemical shifts on aromatic systems. First, what does being near an aromatic system do to protons? If we look at the spectra of 1-napthalenemethanol and then ...
0
votes
0answers
24 views

jury-rigging an automotive catalytic converter for use in the Ostwald Process?

Would it be feasible to jury-rig an automotive catalytic converter for use in the Ostwald Process for the production of Nitric Acid? Given reasonable safety precautions, would it be safe enough to be ...