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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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Can a carbon chain have an alkene/yne alkyl group? Name? [closed]

A side group of an alkane would be a alkyn, like methyl. But could you have a side group of an alkene or alkyne? methenyl? propynyl?
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2answers
31 views

How does acidifying a compound in qualitative analysis make sure any interrupting compounds get removed?

So I've learnt that acidifying a compound for salt analysis is to remove any basic interference and remove interrupting compounds such as carbonates. How does it remove them or what reaction is taking ...
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0answers
26 views

Mechanisms of Penicillin V synthesis [closed]

I am an introductory organic chemistry student; I am looking at the total synthesis of Penicillin V via Sheehan's method. I'm struggling to figure out the mechanisms of each step; could anyone help ...
12
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5answers
599 views

Define, (actually define) the “stability” and “energy” of a compound

When we say a conformer or compound is of "higher energy" than another, are we quantifying energy in terms of the bond strength? Or are we going off of how much energy it takes to break the bond? I ...
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0answers
28 views

What's the difference between CH3 and H3C? [duplicate]

Are there any difference? Why some write CH3 and some write H3C, I'm confused.
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0answers
35 views

Does anybody have any idea what this compound could be? [closed]

This is only part of the entire compound. I cannot interpret the rest of it. If anyone can tell what this compound is based off of this portion of the molecule, please let me know! Thank you! PS- the ...
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1answer
43 views

What happens when HCl is added to acetylene in presence of mercuric ions?

Normal addition of Hydrochloric Acid to acetylene would give me a 1,1 Dichloro product. But I read that in presence of mercuric ions only one molecule of HCl is added to give Vinyl Chloride. Why does ...
0
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1answer
28 views

What is Three Carbon System Tautomerism? [closed]

My friend had told me about this. Does this always happen? What's the mechanism for it.
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1answer
27 views

Highly conjugated compounds and the effects of substiuents

TLDR, what is the effect of electron donating and withdrawing groups on the UV-Vis absorption spectra of pi-conjugated system? For a conjugated system, my understanding is that as the extent of ...
0
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1answer
43 views

Mechanism of hydrogenation of aldehydes [closed]

I wanted to know the mechanism behind the industrial hydrogenation reaction of aldehydes, using nickel or palladium catalyst. Specifically speaking, how is the hydrogen molecule split up?
-1
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1answer
17 views

How does halogenation of alkene occur? [closed]

Is it correct that the halogenation rxn occurs in an anti-addition, if so, why?
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0answers
22 views

Does the reaction product depends on a synthesis method and reagents used in the reaction? [closed]

If the formula of a reaction product is the same, can it have slightly different chemical properties because of different synthesis methods and different reagents used in the process? I ask because ...
-1
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0answers
21 views

How can I remove iron oxide from acidic solution? [closed]

I do some experiment for chemical treatment on dyeing sludge with iron sulphate. This chemical removes dye with chelating with dye. pH of sludge is 12 and after treat with iron sulphate decrease till ...
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0answers
24 views

Why is periodic acid oxidation rate of D-mannose is faster than that of D-glucose [closed]

Why periodic acid oxidation of D-mannose is faster than that of D-glucose. Is it due to the presence of 2 OH groups at C4 and C5 position at the same side and cause steric strain? May that strain ...
-1
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0answers
32 views

Organic Chemistry [closed]

(a)Please indicate the multiplicity of each set of non-equivalent protons in the compound above.(Ibuprofen) (singlet, doublet, etc.)? (b)How many peaks would you predict would appear in the Carbon-13 ...
2
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0answers
40 views

Mechanism for removal of pesticides from fruit by sodium bicarbonate

When Googling around for methods to remove pesticides from fruits and vegetables, a study commonly referred to from some news sites (e.g. here and here ) is one where soaking apples in a sodium ...
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0answers
18 views

Orientation in tri substituted benzene [closed]

Discuss the directive influence of substituent on aromatic system when three groups are already present on aromatic system
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0answers
37 views

How to check whether milk powder (dry milk) is real? [closed]

Please tell me simple tests that can be done at home or in a fundamental chemistry lab.
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0answers
16 views

How would one determine the yield of primary vs. secondary hydrohalogenation addition products?

For example, if I was to perform the following reaction: $\ce{CH3CHCH2 + HBr -> CH3CHBrCH3 + CH3CH2CH2Br}$ How would I quantitatively determine the relative yield of the primary and secondary ...
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0answers
16 views

Is this the most stable chair conformer? [closed]

Is this the more stable chair conformer or the opposite one where the two axial groups will become equatorial?
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1answer
35 views

Reaction between phenylamine and halogens

I understand that phenylamine is considerably more reactive than benzene, meaning that it is able to react with bromine water to give 2,3,6-tribromophenylamine. But I was then wondering why I haven't ...
1
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1answer
32 views

Definition of an “equivalent” [duplicate]

What does it mean to add "1 equivalent" of something? I looked it up on google and couldn't really find a good explanation for it. Thanks!
-1
votes
1answer
42 views

Stability of alkadienes

Which of the following is the most stable? (i) Conjugated alkadiene $(\ce{CH2=CH-CH=CH2})$ (ii) Isolated alkadiene $(\ce{CH2=CH-CH2-CH=CH2})$ (iii) Cumulated alkadiene $(\ce{CH2=C=CH2})$ (...
-1
votes
1answer
24 views

Absorbance maxima of polyenes [closed]

Can anyone tell me how to approach this question from USNCO 2013?
0
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1answer
33 views

Naming this organic compound [duplicate]

What’s the name of the following compound? $$\ce{CH3C(p-ClC6H4)2CH(Br)CH3}$$ My teacher said that she strongly thinks( with another teacher) that it should be 3-bromo-2,2-bis-(4-chlorophenyl)butane, ...
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0answers
31 views

Comparing acidity in 3,4-dihydroxyfuran-2(5H)-one and 2,3-dihydroxycyclopent-2-en-1-one

I have two compounds with two hydrogens namely (a),(b),(c) and (d). I have to compare the acidity of the following hydrogens. My approach: I removed the hydrogen atoms one by one and compared the ...
4
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1answer
49 views

The oxidation of aldehydes and alpha-diketones with peroxy compounds

Recently, I have been reading up on the Baeyer-Villiger (BV) oxidation. The oxidation is most commonly discussed for ketones. However, the oxidation also works for aldehydes and $\alpha$-diketones (...
1
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1answer
43 views

Is common ion effect applicable on two strong electrolytes

Consider the nitration of benzene using mixed conc. $\ce{H2SO4}$ and $\ce{HNO3}$.If a large amount of $\ce{KHSO4}$ is added to the mixture the rate of nitration will be : Faster Slower ...
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votes
1answer
52 views

Mechanism for chloromethylation of Salicylaldehyde [closed]

Reaction mechanism for following reaction : Salicylaldehyde + formaldehyde +con. HCl $\ce{->}$ 5-(Chloromethyl)salicylaldehyde
-1
votes
1answer
32 views

Benzilic acid rearrangement

I'm in need for the exact mechanism of the above reaction. I attempted some tries(mentioned in the mechanism above) and I felt the yield quite unsatisfactory. - the last step remains stuck in an ...
0
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0answers
34 views

Nucleophilic addition - Propanal vs Benzaldehyde

According to my school textbook, carbon atom of the carbonyl group benzaldehyde is less electrophilic than that of propanal because polarity of the carbonyl group is reduced in benzaldehyde due to ...
2
votes
1answer
68 views

Why other benzene derivatives do not undergo nitrosation

Solomon and Fryhle $11 th$ ed : Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction. I agree that if there is a primary or secondary ...
-1
votes
0answers
23 views

Resonance - Acids and Base [duplicate]

Which of the two protons is more acidic? The key said the red one, but can't blue one also have as many resonance structures as the first one? Why is red more acidic?
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0answers
35 views

Preference for tin or iron in the reduction of nitrobenzene

My NCERT book(Class 12) said the following for reduction of nitrobenzene using $\ce{Sn/HCl}$ and $\ce{Fe/HCl}$ : Now, I have been following this mechanism for this particular reduction, and it seems ...
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0answers
65 views

Nitration of m-bromochlorobenzene

1) What could be the most plausible explanation to the very low percentage of the nitro group attacking the site between bromine and chlorine? - is it solely because of steric hinderence - or is it ...
0
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0answers
17 views

Birch reduction- 1,4-cyclohexadiene over 1,3-cyclohexadiene [duplicate]

While reading of birch reduction I was confused as of why 1,4-cyclohexadiene is prefered over 1,3-cyclohexadiene, the latter which ought to have been the major product due to conjugation. One of the ...
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votes
1answer
37 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
votes
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
62 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
46 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
29 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
30 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
votes
1answer
31 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
12 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
41 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] "...
0
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2answers
51 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
20 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 ...