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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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1answer
38 views

SN2 reactions with primary alcohols [closed]

A problem I was recently working on poses the following scenario: A student realizes that protonation of an alcohol makes the -OH into a better leaving group. Therefore, he suggested the following ...
0
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1answer
37 views

Does a tertiary carbocation rearrange to another tertiary carbocation?

I strongly believe that a carbocation should not rearrange to another if there are no immediate benefits(like a Greedy Algorithm). The doubt hit me while solving this question. The answer mentioned ...
1
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1answer
70 views

Mechanism of the Gatterman Reaction

Aryl diazonium salt on treatment with copper and the corresponding hydrohalic acid, gives the aryl halide. This reaction is called the Gatterman reaction. What is the mechanism of this reaction? Is ...
1
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1answer
47 views

Order of reactivity of hydrogen halides

Solomon and Fryhle $11^{th}$ edition says : Order of reactivity of HX in the acid catalyzed conversion of alcohols to alkyl halides follows the order : HI>HBr>HCl We can account for this by saying ...
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0answers
30 views

When Tildens Reagent is added to an alkene does the product change to an oxime always?

I was reading about Tildens Reagent when I came across this.. Does this happen always? Or is it when there is only a single hydrogen attached to the carbon?
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0answers
33 views

Direct reaction of fluorine with benzene will give what product?

My book says fluorine will react with benzene vigorously and involve C–C bond breakage. What does that mean and what product will be formed? It also said that the reaction is of no preparative use.
1
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1answer
40 views

What kind of plastic is (really) safe to store vegetable oil?

Storing colza or olive oil in a plastic bottle might be risky since the oil can leach out phthalates and BPA (and others molecules?). Some manufacturers sell "phthalates and BPA free bottles", but ...
1
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1answer
32 views

Degree of unsaturation of naphthalene

Double Bond Equivalent/Degree of Unsaturation 25. Degree of unsaturation in is (a) 6; (b) 7; (c) 8. There are two rings and six double bonds in structure so degree of unsaturation ...
2
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1answer
32 views

Reduction with NH2-NH2 , OH-, and glycol

this question was asked in my exam and I have done it properly until the very third step but unfortunately, although the last step looked like wolfkishner reduction to me I could not do it. My ...
0
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0answers
14 views

Better nucleophile OH- aur OCH3- in aqueous medium

Which of the two, Hydroxide anion OH- and Methoxide ion OCH3-, is a better nucleophile in aqueous medium?? I have 2 arguments both against each other. First, Oxygen atom in methoxide has higher ...
1
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1answer
43 views

Dependence of primary alcohol oxidation on presence of water and “strong” or “weak” oxidants

It is known that the oxidation of primary alcohols can result in aldehydes or carboxylic acids. The product obtained from the reaction is described as dependent on reagents and conditions;[1] "...
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2answers
52 views

How tartaric acid gives Tollen's test?

I wanted to know how Tollen's test is given by tartaric acid. Google searchs say that it belongs to some "Hydroxyl" group. I know that it oxidises aliphatic and aromatic aldehydes along with α-hydroxy ...
1
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1answer
34 views

Calculate pKa for lipids

I would like to calculate $\mathrm{p}K_\mathrm{a}$ of lipid molecules using some software tools. I have tried ChemAxon and compared with ChemDraw professional 16.0 version they are mostly similar. I ...
0
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0answers
25 views

Why meta has low boiling point than ortho isomer

When I was going through haloalkanes I came to know that the boiling point of Ortho is more than meta what is the possible reason behind it I have asked it at several places and I am getting the ...
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0answers
20 views

Resources for hard organic chemistry problems (sophomore level, with answers) [duplicate]

Do any there exist resources for good, deep organic questions (most textbook questions are too easy) which also preferably have answers given so I can check them as I do them? Especially something ...
3
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2answers
79 views

How does existence of alpha and beta form of glucose prove that it exists as a cyclic structure

My book says that Glucose is found to exist in two different crystalline forms which are named as $\alpha$ and $\beta$. Next it says that This behaviour could not be explained by the open ...
0
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2answers
62 views

How to identify the structure of an organic acid based on its reactivity, mass and NMR spectrum?

Taken from OCR A Chemistry Unified Chemistry Sample Paper. Information about a monobasic organic acid D is shown below. D reacts by both electrophilic substitution and electrophilic ...
3
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0answers
36 views

Stability of carbocation

While comparing the stability, as the $\ce{CH3}$ group is electron donating, the first structure should be more stable due to this reason. But apparently the second one is more stable. Is there ...
3
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0answers
30 views

How can I preserve chlorophyll for long periods of time?

I'm currently working on a XIX century photographic process called Anthotype. It relies on organic colored substances that fade when exposed to sunlight. For the substances I've tried alcoholic ...
3
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1answer
43 views

Is the existence of chirality center equivalent to chiral?

To make my question more clear, I want to ask two questions: Is it possible for molecule to be achiral even though molecule has chirality center? Is it possible for molecule to be chiral even ...
1
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2answers
39 views

Is there a replacement for glacial acetic acid in determining peroxide value

I am not allowed to use glacial acetic acid at my school, which all procedures online for finding the peroxide value of oils use through an iodometric titration. Is there a replacement?
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0answers
43 views

What is the full mechanism for oxidation of toluene to benzoic acid using permanganate? [duplicate]

I have managed to get some of the way (I think): I am particularly interested in the full mechanism i.e. all the curly arrows that take you from toluene right through to benzoic acid.
6
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2answers
270 views

Recrystallisation of dibenzylideneacetone

Recently, I carried out the synthesis of dibenzylideneacetone. I had a lot of problems with the purification process, especially the part involving recrystallisation. I was instructed to carry out the ...
1
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1answer
60 views

Which has a greater dipole: chloroform (CHCl3) or trichlorofluoromethane (CCl3F)?

Does chloroform have a greater dipole because the $\ce{C-H}$ dipole is weaker than $\ce{C-Cl}$ dipole thereby making the overall net dipole greater in chloroform, as opposed to trichlorofluoromethane ...
1
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2answers
76 views

Which one is more acidic – 3,5-dinitrophenol or 4-nitrophenol

I’m confused because in 3,5-dinitrophenol, the inductive effect is dominating whereas in 4-nitrophenol the mesomeric effect dominates. So which one should we consider for acidity?
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2answers
53 views

Nail polish chemistry question [closed]

When I read my ingredients on my nail polish remover, it has water as its first ingredient. Why does nail polish have water, yet the warnings still say its flammable?
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0answers
29 views

Alkylation of acetophenone

When the NaOH deprotonates the hydrogen off the carbon, I thought there would be a resonance structure, with the negative charge being on both the oxygen and carbon. Since the oxygen is more stable ...
0
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1answer
57 views

Effect of pH on charge of jasmonic acid

It has been such a long time, that I totally forgot how it works. I am interested in the charge of jasmonic acid at different concentrations. More specifically, I want to know at what pH my molecule ...
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0answers
44 views

How to name halide ether? [duplicate]

$\ce{CH3-O-CH2-CH2Cl}$ is named as 2-chloro-1-methoxyethane, but is called 1-bromo-2-ethoxycyclohexane. If in second compound bromo is given priority over ethoxy, then why in first compound methoxy ...
4
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0answers
59 views

Shouldn't the 5-membered ring expand to a six membered one in this nucleophilic addition reaction?

I am dealing with a problem involving addition of $\ce{HCl}$ to a ring: According to what I think, the ring should expand to a six-membered following carbocation formation at the tertiary site, as a ...
10
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2answers
2k views

What would the chemical name be for C13H8Cl3NO

Formula C13H8Cl3NO SMILES C1=C(C(=CC(=C1)Cl)Cl)N(C(C2=CC=CC=C2)=O)Cl I found the diagram on the left in a book and drew the one on the right using https://pubchem.ncbi.nlm.nih.gov/...
1
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1answer
58 views

Mechanism with hypohalite in haloform reaction

The haloform reaction is usually done in a solution of NaOH and $\ce{I2}$ (or indeed, any halogen). Now the first part of the reaction mechanism in the wikipedia page and in the most organic books ...
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0answers
61 views

Action of H2S and OH- on an alkyl halide?

What would be the action of $\ce{OH-}$ and $\ce{H2S}$ on 2,6 dichloroheptane? I came across this question in my organic chemistry workbook but I have simply never seen a question of this type before. ...
8
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3answers
184 views

Why are carbons of Inositol chiral centers?

I was asked to draw all possible stereoisomers of inositol (1,2,3,4,5,6-cyclohexanehexol). To obtain the answer I had to assume that all six carbons of the molecule are asymmetric, which (bearing in ...
2
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0answers
31 views

The use of silyl enol ethers over aza-enolates

I do not quite understand how alkylations using tertiary halides would work better with silyl enol ethers, compared with using the aza-enolate nucleophile. The following was mentioned in Clayden, ...
1
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1answer
46 views

What is the expected number of rings obtained in the following ring formation process?

Refluxing, say, one mole of 1,5-dibromo-pentane with excess ammonia in ethanol can result in the formation of rings. (e.g. $1\lambda^2$-piperidine) However, it is also possible for the 1,5-dibromo-...
4
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2answers
60 views

Finding major product when bromonium compound is acted upon by a nucleophile

The original question is:- The major product obtained in the following conversion is:- (Note that Me here means methyl group) The initial step would be the formation of a bromonium ...
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0answers
50 views

Which group will show mesomeric effect?

If both $\ce{-CH2+}$ and $\ce{-NO2}$ groups are attached to benzene ring then which group would be more effective in showing $\ce{-M}$ effect?
7
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2answers
191 views

Melting point of unsymmetrical dimethylhydrazine vs 1,2-dimethylhydrazine

Unsymmetrical dimethylhydrazine ($\ce{H2NN(CH3)2}$) has a melting point of −57 °C, but its isomer, 1,2-dimethylhydrazine ($\ce{(CH3NH)2}$) has a melting point of −9 °C. That looks to me like a ...
1
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1answer
146 views

Anti-aromatic or Non-aromatic [closed]

Please tell if the 2 given conpound are Anti-aromatic or Non-aromatic, I have confusions arising due to incosistent facts all around internet some of them are as follow : 1.) Arguments for ...
1
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0answers
33 views

Acidity comparison between 4-hydroxybenzaldehyde and methanoic acid

Acidity is dependent on charge dispersal. Greater the charge dispersal in conjugate base greater the acidity (assuming that both acids being compared have similar stablities). So in the case of 4-...
5
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1answer
67 views

Why is a 7-endo radical cyclisation favoured over a 6-exo in this synthesis?

Normally, according to Baldwin's rules, 3-exo to 7-exo cyclisations are preferred over endo cyclisations. But in the following example, a 7-endo-trig reaction is favoured over a 6-exo-trig and I am ...
3
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1answer
116 views

What is the mechanism of azulene synthesis?

In the Organic Syntheses preparation of azulene (http://www.orgsyn.org/demo.aspx?prep=CV7P0015) there are two reactions. First is a clevage of the C-N bond in pyridine and the second one is the ...
2
votes
1answer
282 views

Why is Acetic acid (pKa = 4.76) stronger than carbonic acid (pKa = 6.36)? [duplicate]

In order to try and understand this, I evaluated it via stability of conjugate bases. The acetate vs carbonate ion. The only difference is what's attached to the carboxyl group, the $\ce{-CH3}$ and ...
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0answers
30 views

What are the pi-MOs in anisole like?

The $\pi$-orbitals of benzene are well known and given in any standard undergraduate textbook. When considering anisole, phenol, etc, a lone pair in a p orbital of the O can delocalise into the $\pi$-...
0
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1answer
43 views

Preference for basic conditions in ester hydrolysis

It has occurred to me that it is very common see the use of basic conditions for ester hydrolysis in various syntheses. One such sequence commonly seen in the case of the malonic ester synthesis is: $...
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1answer
33 views

Ranking basicity from a structure

I just came across this question in my revision. I selected (A) but the correct answer is (D). Could someone explain where I am going wrong? I is least stable --> most reactive --> most basic Cl is ...
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0answers
13 views

Is my mechanism for the reaction, where FabH catalyzes it in fatty acid biosynthesis, complete and correct?

I need to write a mechanism for the following reaction. In this reaction, FabH is the protein that catalyzes the reaction in fatty acid biosynthesis. The beta keto carboxylic acid decarboxylates to ...
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0answers
60 views

Know if a molecule is viable with Python [closed]

I'm working with python and I'd like to know if someone knows a python module which is able to check if a molecule is chemically viable (valence, connectivity constraints ...), or not. I know there is ...
1
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1answer
76 views

Mechanism for Bial's test

In biochemistry laboratory, it's common for undergraduate students to perform identification of carbohydrates and its functional groups. Bial's test, a method to check if any pentose is present, is ...