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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
84 views

Nomenclature of an organic compound with benzene and double bonds

How would the following compound be named? Attemp of solution I believe is 4-phenyl-1,2-pentadiene
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1answer
31 views

How to reduce specific gravity of a brine solution? [closed]

We have prepared a brine solution ($\ce{NaCl}$ + water). Its present specific gravity is more than 30 percent. We need to keep the specific gravity between 28 and 30 percent. Should we add more water ...
4
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2answers
86 views

Which one has higher priority according to Cahn–Ingold–Prelog rules?

Which one has higher priority according to Cahn–Ingold–Prelog rules? (1) $\ce{-CH2OH}$ and $\ce{-CH=CH2}$ (2) $\ce{-CH2OH}$ and $\ce{-C(CH3)3}$ The answer says $\ce{-CH=CH2}$ has higher ...
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0answers
39 views

Heating Dry Benzenediazonium Chloride

If we heat BDC with water then phenol is formed. I was wondering what would happen if we heated dry benzenediazonium chloride. I know that on heating benzenediazonium fluoroborate we obtain ...
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1answer
32 views

Gabriel Phthalamide Reaction

Can we use acid chloride in place of alkyl chloride in Gabriel Phthalamide Reaction? Maybe it can be used as process to synthesize amides.
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1answer
56 views

Reaction mechanism for the conversion of acyl hydrazide to acyl azide

How is an an acyl hydrazide converted into an acyl azide in the presence of $\ce{HNO2}$? According to me, the $\ce{-NH2}$ group of hydrazide will get converted into $\ce{-N2+}$ through $\ce{HNO2}$. ...
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1answer
102 views

Why Guanidine is called as strong base

I've studied pka of H2O as 15 and anything with a pka lower than it should be a acid . Guanidine has a pka of 13.8 and is being called as strong base . Why is it so. https://en.m.wikipedia.org/wiki/...
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0answers
35 views

What takes place in this transformation of the 1,3-dicarbonyl?

I was just looking at a particular synthesis method on the Organic Chemistry Portal when I saw a particularly puzzling step, involving a 1,3-dicarbonyl compound. The step which I am puzzled by is ...
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1answer
28 views

Reagents in Krapcho's decarboxylation

Krapcho's decarboxylation is a reaction involving esters with a electron-withdrawing group $\beta$ to the carbonyl group and halide ions. It is typically conducted with $\ce {LiCl}$ and $\ce {DMSO}$ ...
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2answers
137 views

How to convert but-2-ene to but-1-ene? [closed]

How can we convert but-2-ene to but-1-ene? Is it even possible, since but-2-ene is the more stable one.
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1answer
23 views

What is the molecular formula of 2-ethynyloctahydro-1H-indene?

I thought the formula for this $\ce{C11H15}$, but it's not. I need assistance in finding the proper formula:
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0answers
19 views

Cross Cannizzarro reaction for ketones

I want to ask that cross cannizzarro could be possible between any aldehyde + ketone mixture(without alpha H) and we get products as aldehyde get oxidised and ketone get reduced(along with self ...
0
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1answer
59 views

What is the balanced equation of BH3/THF with an amide to form an amine? [closed]

I am doing a green chemistry project as an undergraduate and need the balanced equation to complete the calculations. I cannot find the right information online so any help would be greatly ...
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0answers
24 views

Monitoring amino acid esterification

I am trying to monitor the esterification of a non UV active amino acid.I used thionyl chloride and Methanol as reagents. As amino group is unprotected, Ninhydrin should give positive result for both ...
2
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0answers
57 views

Stability of methoxy-methyl and tropylium carbocations

Which is expected to be more stable: methoxy-methyl carbocation $(\ce{CH3-O-CH2+})$ or tropylium $(\ce{C7H7+})$ cation? I think because oxygen would donate its lone pair so there will be complete ...
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0answers
81 views

Alkoxide as a leaving group in hydrolysis of ester

In the base catalysed hydrolysis the hydroxide ion adds to the ester to form a tetrahedral intermediate, after which the alkoxide ions leave and forms carboxylate ion and alcohol. Also we find the ...
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1answer
72 views

Mechanism of the reaction [closed]

I came across the following reaction,about which I was ignorant till now.Can anyone guide be regarding it with suitable mechanism.
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1answer
59 views

Stability order of carbocations [duplicate]

These are some of the most stable carbocations, but what is the relative stability order between them. According to me it should be: C>D>B>A........ I came to this conclusion because both C and D ...
2
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2answers
117 views

Product of oxidation of alkanes

I'm trying to find the product of the oxidation of iso-butane using KMnO4, i know that alkanes undergo step wise oxidation with strong oxidising agents to finally give carboxylic acids.. With straight ...
0
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1answer
59 views

Effect of substituents on Ullmann reaction

This question that I recently encountered asked what the most suitable substrate for the Ullmann reaction would be. The answer given is (b) but I think it has to be (d) as the nitro group acts as EWG ...
0
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1answer
87 views

Nucleophillic addition vs SN2

The following question came in Paper 2 of JEE Advanced 2014- Here we have $\ce{CH3-}$ as the nucleophile. There are 2 possible attacks: SN2 type attack on the chlorine group. Nucleophilic addition ...
0
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1answer
40 views

Hybridization of carbon atoms present in the smallest ester?

I found this question in the Resonance DLPD Organic Chemistry book on Page 55: What is the hybridization of carbon atoms present in the smallest ester? The smallest ester as far as I know is ...
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0answers
18 views

Are linear alkanes polymers? [duplicate]

Let me ask a basic question. Wikipedia defines a polymer as A polymer is a large molecule, or macromolecule, composed of many repeated subunits. Now, can we think of a large linear alkane as a ...
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0answers
15 views

Stability of carbocation on doubly bonded carbon [duplicate]

What can be said about the stability of the following carbocation? I think that it would have something to do with hybridisation as, clearly one carbon is sp hybridised and the other is sp2. Can ...
1
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1answer
67 views

Bond rotation in buta-1,3-diene

Why don't all the atoms in s-cis-1,3-butadiene lie in one plane? All carbon atoms are $\mathrm{sp^2}$ hybridised and I feel that there would be no $\ce{C-C}$ bond rotation due to the conjugation ...
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1answer
29 views

product of the reaction iodine with alcohol [closed]

I have a multiple choice question. The product from the reaction of iodine monochloride, ICl, with pent-1-ene is: A CH3CH2CHICHClCH3 B CH3CH2CH2CHICH2Cl C CH3CH2CH2CHClCH2I D CH3CH2CHClCHICH3 the ...
2
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0answers
36 views

most frequently used organic (name) reactions

The situation: Beside the relevant inventory in the Merck index, organic-chemistry.org lists 243 name reactions (as counted on 08-Feb-2018), the compilation by Kurti and Czako includes "250 selections"...
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2answers
44 views

Perpendicular orbitals in aryl and vinyl carbocations? [duplicate]

This point (iv) has been given under reasons for extremely low reactivity of aryl and vinyl halides. I cannot understand it. First of all, isn't the positive carbon atom in phenyl as well as vinyl ...
0
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0answers
37 views

Ozonolysis products of ortho-methyl toluene

What yield of different products will I obtain upon ozonolysis of o-methyl toluene? Assuming 2 moles of the compound to react(each with different positions of double bonds), I get the possible ...
-1
votes
1answer
26 views

Lewis structure of a compound [closed]

What is the correct lewis structure of ammonium cyanate ion? I do have a structure but it seems partially correct. If I'm wrong, then please inform that also.
-1
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1answer
45 views

Why is the carbanion resonance structure being used in the aldol condensation mechanism?

In the above mechanism's first step, what motivates the use of the carbanion resonance structure of the enolate ion if the negative charge is better localized on the more electronegative oxygen? Edit:...
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2answers
52 views

Less substituted vs more substituted alkene [closed]

In general, more substituted alkenes are more thermodynamically stable. However, in certain cases such as enamine alkylation, the less substituted double bond is favored. How do we know that which is ...
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0answers
25 views

Oxidation products of propylene glycol

Working in a building that uses propylene glycol (PG) as antifreeze in a hydroponic heating system. With complaints of chemical odors in offices, I conducted air sampling for glycols, aldehydes, and ...
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1answer
33 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 ...
-1
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1answer
27 views

Organic Layer/Aqueous Layer Question [closed]

I could not answer this question, it would be appreciated if someone could help.
2
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2answers
101 views

How does di-isobutylaluminium hydride ( DiBAl-H ) reduces carboxylic acid

$\text{DiBAl-H}$ reduces by electrophilic attack and provides hydrogen by $\text{H}^-$ transfer. Unlike $\text{LiAlH}_4$ it does not directly provide $\text{H}^-$ ion. So it should not undergo acid ...
2
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1answer
32 views

Rationalising the reactivity of phosphoryl chloride

$\ce {POCl3}$ is a reagent well-known for enacting various functions in organic synthesis. For example, together with pyridine, it is able to dehydrate alcohols to give alkenes. Also, reacting it with ...
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1answer
60 views

Reasoning about a separation problem [closed]

Describe exactly how you would go about separating a mixture of the three water-insoluble liquids, aniline (b.p. 184 °C), n-butylbenzene (b.p. 183 °C) and n-valeric acid (b.p. 187 °C), recovering each ...
0
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1answer
51 views

Strength of a nucleophile [closed]

A nucleophile should get better at its job if it can donate a pair of electrons more easily. We say that a more electronegative atom should be less nucleophilic , generally. I understand this is ...
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1answer
44 views

Why does acetylene form a triple bond? [closed]

I'm going through basic tutorials about hybridisation, but I am having trouble understanding the reason for drawing a triple bond for C2H2. It seems to me that a double bond is enough for the octet ...
1
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1answer
309 views

What would be the name of this compound? [closed]

Although I assume this compound is likely unable to be formed, my chemistry teacher put it up on the whiteboard to show the extent of what you can name using IUPAC nomenclature, out of interest I ...
0
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2answers
44 views

Confusion in the name of this organic compound

I think the name of the above compound should be 3-Ethyl-2-methylcyclohex-1-ene. However, according to my book (Organic Chemistry Resonance DLPD, page #43, question #5), this organic compound is 6-...
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0answers
28 views

Oil + UV radiation = cholecalciferol?

According to a web site about health (Antranik): The oil that naturally comes from our skin is a type of cholesterol. Whenever we stand under direct sunlight, the ultraviolet rays react with ...
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0answers
62 views

Acid catalyzed enolization and alpha hydrogen

In acidic catalyzed enolization of butan-2-one: We have 2 alpha hydrogens available. From the mechanism of acid catalyzed enolization there is a certain carbocation character at the carbonyl carbon ...
7
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1answer
58 views

Bond cleavage of 3 membered cyclic ring on heating

I was told to propose a mechanism for the following conversion: One obvious step is the conversion of cyclic ketal to ketone because of acidic conditions. But I am unable to understand how the three ...
1
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2answers
88 views

Order of Nucleophilicity

I know this question has been asked many times but I need to confirm this doubt which has been pestering me for the past few days. Suppose in an $\mathrm{S_N2}$ reaction (in polar aprotic solvent) we ...
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1answer
46 views

Question about the cyclic hemiacetal form of compounds [closed]

Why is D not a valid answer for this question?
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1answer
73 views

Reaction between carboxylic acids and amines

Would some be able to explain why when I mix a carboxylic acid, like ethanoic acid, and an amine, say ethylamine, I get ethylammonium ethanoate. But when I mix a bi-functional group carboxylic acid (...
1
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1answer
47 views

Why do double bonds cause kinks in fatty acid chains?

Fatty acids can either be saturated or unsaturated. If they are saturated, they stack easily and form solids at room temperature. If they are unsaturated, however, double bonds are introduced, and ...
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2answers
89 views

Why does delocalization lead to stability? [duplicate]

If the electrons are relatively more stable when they are delocalized than when they are localized between two atoms, then why do we have bonds formed in the first place? Forming of bonds between two ...