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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6
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3answers
4k views

Alkane nomenclature - choosing the parent chain - maximize or minimize substituents?

Given structure: Here's my go at it. The longest carbon chain has 10 Carbon atoms, so the root -- decane. Next: let's take the substituent in position 3, we get <...
2
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2answers
490 views

Dyes that can stain oil and water

Is there such a thing as a dye that can stain both oil and water? In other words, does anyone know of an amphiphilic dye? Maybe a surfactant that is also a pretty shade of blue? Or maybe turn one ...
12
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3answers
11k views
1
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1answer
77 views

Rate of solvolysis of allyl and alkyl halides

Suppose I have 2 compounds, 3-chloropropene and 1-bromo-1-methylcyclohexane. Without knowing the values, how can we compare the rate of solvolysis? My attempt: Resonance is quite dominant character ...
0
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0answers
24 views

Why does 1,2-dihydroxybenzene have higher boiling point than monohydroxybenzene? [duplicate]

I studied that any kind of dihydroxybenzene has higher boiling point than monohydroxybenzene, and among the dihydroxybenzenes, I understood that because of inter molecular hydrogen bonding they have ...
1
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1answer
612 views

Inductive vs conjugation effects in ester hydrolysis

I just came across the following problem about alkaline ester hydrolysis: Since all of the substituents are in the para position, I immediately thought about the ability of those substituents to ...
2
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1answer
34 views

Can I solubilize lemon essence in water somehow?

I have a water based solution (95% water, the rest are salts) to which I want to add a lemon fragrance. I bought "water based lemon essence", but upon putting a mere drop in about 500 mL, ...
1
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1answer
95 views

Finding the right order of carbocation stability

I should put these carbocations in decreasing order of stability. Structure 1 is a primary carbocation. Structure 2 is a secondary carbocation. Structure 3 is a tertiary carbocation. Structure 4 (a ...
3
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1answer
137 views

White growth on unopened bottle of chlorotrimethylsilane

I have a white, moldy-like substance that has been growing nearing the cap of an unopened glass container filled with TMSCl. It has spread to form a thin, powdery coating on all of the other ...
2
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1answer
56 views

TEMPO Radical Analogue

After investigating what makes the persistent radical TEMPO stable, I was wondering if another compound which is more feasible for my needs would be comparable to it. Would oxidizing 2,2’-dimethyl-...
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0answers
13 views

Is AIBN compound able to start homolysis? [closed]

I would like to aks if AIBN compound can cause homolysis of halogen molecule
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1answer
17 views

Relation between Dipole Moment and Polarity of a molecule [closed]

Is it necessary for a molecule to have a net dipole moment to be a polar molecule?
0
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1answer
76 views

Effect on acidity of benzene due to electron withdrawing groups

With respect to the compounds I–V, choose the correct statement(s). Compound II becomes more acidic when it has a $\ce{-NO2}$ substituent. The acidity of compounds follows the order I > IV > V &...
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0answers
11 views

Does pressure affect homolysis?

I would like to know what is better for homolytic fissisng and why. A) high temperature and high pressure B) high temperature and low pressure I think that B is the solutiot, because before the ...
-2
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0answers
14 views

Which catalyst can cause homolysis? [closed]

What catalyst from theese can cause homolysis of halogen molecule alone? Alone - for instance if you use high temperature, you do not need UV and if you use too much UV you do not need high ...
-1
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1answer
27 views

What happens if you do not allow time for an exothermic reaction to cool down?

I realise I did not give some time for the chemicals (which are releasing heat during an exothermic reaction) to cool down first and instead, I added another chemical substance to the reaction mixture ...
-2
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0answers
17 views

How can someone in the lab synthesize n-allyl-4methyl-benzenesulfonamide from 4-toluenesulfonyl and allylamine

I am trying to figoure out the conditions and choice of solvents and catalysts in order to run this synthesis.
-4
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1answer
42 views

iupac name please? [closed]

I am kind of confuse here whether to number $\ce{NO_2}$ or double bond in the ring.
1
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0answers
23 views

Hydroboration, steroselectivity and anti-markovnikov product [duplicate]

My first question has to do with the fact that Hydroboration produces an anti-markovnikov product, why?. I don't see how that happens. A wikipedia artical says that B has a partial positive charge ...
-1
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0answers
23 views

Dilution confusion

I have run into what I imagined would be simple mathematics, but it turns out I need some help. My problem is I have a bottle of Geobacillus stearothermophilus and the concentration of the spores is $\...
0
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0answers
21 views

Removing denatured Crystalbond?

I have some water-soluble crystalbond that is attached to silicon and, because of some overheating (to about 150 Celcius) during a final processing step, the crystalbond seems to have charred (white/...
9
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4answers
17k views

Can you melt wood?

We talked about it in our chemistry class but we couldn't get to a conclusion, any help?
1
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0answers
37 views

phenolsulphonic acid

Phenolsulfonic Acid( PSA) is produced after sulphonation of Phenol at around 100 degrees. They use this product in tinplating. Once a stable PSA is formed after sufficient reaction , unreacted ...
0
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0answers
40 views

Does 3‐ethyl‐1,1‐dimethylcyclohexane have a stereocenter?

I knew that we have a stereocenter if the carbon is bonded to four different groups. According to the stereocenter rules, I should have $\ce{CH2}$ bonded to the carbon of the stereocenter (marked with ...
6
votes
1answer
163 views

Why are hydrogen bonds in an antiparallel beta sheet stronger than those in parallel beta sheets?

Beta sheets are illustrated as such in most diagrams, where: In an antiparallel β-sheet, the polypeptide strands are arranged such that a $\ce{C=O}$ and an $\ce{NH}$ from adjacent strands face each ...
5
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1answer
104 views

Mechanism of ring opening of amine combined with formylation

What is the mechanism for this reaction? The tertiary amine is converted into an amide and the ring gains a double bond. I can't figure out how the C-O double bond would be formed.
12
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3answers
15k views

Converting a cis-alkene to trans-alkene

I was thinking about simple method to convert a cis-alkene alkene like cis-2-butene to trans-2-butene. I came up with this method (the method can also be used to convert trans alkene to cis alkene): ...
6
votes
1answer
673 views

In the Haworth projections of D and L glucose, is the stereochemistry at every carbon except the anomeric carbon just inverted?

I'm having a bit of trouble grasping sugar stereochemistry. Using glucose as an example, if you cyclize D and L glucose, is the stereochemistry at every carbon just inverted from the other form? ...
1
vote
1answer
76 views

Are phenyl and allyl groups in prop-2-enylbenzene coplanar?

Wouldn't C1 and C2 in prop-2-enylbenzene be on the same plane as that of the phenyl ring, right? If the double bond connected to C2 was between it and C1, they would be, but is it correct that now ...
1
vote
1answer
34 views

Why is para-aminobenzoic acid more acidic than ortho-aminobenzoic acid?

Compare the acidic strength of o-, m-, p-aminobenzoic acids. I got that meta will be the most acidic as it won't be able to show R+ effect of $\ce{NH2}.$ But among the other two, i.e. ortho and para, ...
1
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2answers
20k views

When to use iso and sec while naming compounds in alkyl halides?

I am having confusion on when to use iso- or sec- while naming the alkyl halides?
8
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1answer
131 views

Why is quinone mono oxime more stable than 4-nitrosophenol?

When we do nitrosation of phenols, we get para-nitrosophenol as the major product, which tautomerises to quinone mono oxime. This article states that it largely exists in the quinonoid form. My ...
23
votes
4answers
31k views

Why is acetic acid more acidic than phenol?

Acetic acid (ethanoic acid, $\mathrm pK_\mathrm a \approx 5$) is more acidic than phenol ($\mathrm pK_\mathrm a \approx 10$), which is reflected in their reactivity with a weak base such as sodium ...
0
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0answers
14 views

Keto Enol tautomerism [duplicate]

I don't understand why the keto form is present more at equilibrium. Yes I know that for phenols or instances where the enol form can have H-bonding the enol form is preferred, but generally I have ...
2
votes
1answer
508 views

Soxhlet extraction condenser - addition of compound to refluxing setup

I've never used Soxhlet apparatus before and I have troubles understanding how to properly perform the following step from my protocol: To a gently refluxing suspension of 1 g Lithium aluminium ...
3
votes
2answers
97 views

Is it correct to look at plane of symmetry in substituted cyclohexane for determining a meso compound?

I read this question and it's answer by @orthocresol. Now, he has written that the compound in question is meso not because there is a plane of symmetry but because of the rapid flipping of the ...
-1
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0answers
27 views

Is (Z)-1-bromo-2-chloro-2-fluoro-1-iodoethene optically active or optically inactive? [closed]

Is (Z)-1-bromo-2-chloro-2-fluoro-1-iodoethene optically active or optically inactive? Need a solution of the given problem. My test says it is an optically inactive compound but there seems to be no ...
0
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0answers
15 views

Concentration of organic acids in lichens/rock substrates/soil (particularly oxalic and citric acid)

I am trying to design an experiment testing the efficacy of lichen acids to solubilize and mobilize nutrients from minerals in a lunar regolith simulant. My research so far indicates that oxalic acid ...
4
votes
1answer
127 views

Is cyclohexane‐1,3‐dicarboxylic acid a correct IUPAC name?

I did the numbering by taking all the functional groups in principal chain (scheme A), but my teacher did it differently and proposed the name cyclohexane‐1,3‐dicarboxylic acid (scheme B): The ...
13
votes
4answers
10k views

Why does having equivalent resonance structures give more stability?

Although the phenolate ion has more resonance structures (4) compared to acetate ion (2), acetate is more stable because it has two equivalent resonance structures of same energy. Why does having ...
-2
votes
1answer
34 views

Why these compounds don't show and show Geometrical isomerism? [closed]

I was recently studying organic chemistry related to Isomerism. I have doubt based on an example that is, Why Cumulenes show GI? Why 1-chloro cyclohexene don't show GI?
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0answers
35 views

3-propyl-penta-1,3-diene vs 3-ethylidene-hex-1-ene

From the rules that I know, I will name the above compound as 3-propyl-penta-1,3-diene because maximum number of functional groups (double bonds in this case) are in the five numbered carbon chain. ...
-2
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0answers
72 views

Which of the structures is more stable? [closed]

Please Explain me which of the following structures is more stable. Is structure (b) having cross conjugation? According to me, (b) should be more stable than (a) because free radical at primary ...
-2
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0answers
16 views

Factors Affecting Rates of Reaction [closed]

1-Bromopropane reacts with sodium hydroxide solution to give propan-1-ol. The hydroxide ions replace the bromine in the organic molecule: $$\ce{CH3CH2CH2Br + OH- -> CH3CH2CH2OH + Br-}$$ This is a ...
0
votes
1answer
29 views

What is the electrophile in Perkin's condensation reaction?

In Perkin's reaction, an aromatic aldehyde reacts with an acid anhydride to give an alpha-beta unsaturated aromatic acid. Which reactant is the electrophile and which one is the nucleophile?
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0answers
18 views

How to achieve a homogeneous mixture of nutrients in all measurements of dog food? [closed]

I have obtained the minimum daily requirements for nutrients for my 2 dogs. I have a freeze dryer and I want to make my dog some food. Knowing the MDR for the dog how to I mix up the dog food so that ...
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0answers
28 views

How to figure out the molecular formula of organic molecule formed from CO2 and H2O? [closed]

I am stuck with this problem for a few days now. I have the equation, $$\ce{C_xH_yO_z + O2 -> CO2 + H2O}$$ and data Mass of Sample (g) Mass of $\ce{CO2}$ (g) Mass of $\ce{H2O}$ (g) 0.5964 0.3048 ...
2
votes
1answer
2k views

Polarity and acid strength in alcohols

I'm totally confused about the relationship between the polarity and acid strength of a given compoud. Take the case of alcohols itself, it's said that primary alcohols have greater acid strength ...
-2
votes
0answers
27 views

Bioorganic PKS Exam Revision

Hi all, going through exam revision for third-year Chemistry Exams. I'm coming up blank on some bioorganic questions on Poly Ketide Synthases. In the question it asks follows: 1)What post-...

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