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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
30 views

Aromaticity of conjugated cyclic ketones [closed]

Consider the following compounds: Cyclopenta-2,4-dien-1-one Cyclopent-2-en-1-one In both compounds, I can visualize a resonating structure in which the ring follows Huckel's rules by: The $\ce{C=O}$...
2
votes
1answer
38 views

Bromohydration regioselectivity

In which of these cases would the addition of $\ce{Br2/H2O}$ be highly regioselective? $$\ce{CH3CH=CHCH2CH3}$$ or $$\ce{(CH3)2C=CH2}$$ since both are asymmetric alkenes, how do I answer the question?...
5
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1answer
63 views

The maximum no. of isomers (including stereoisomers) that are possible on mono-chlorination of the compound: 3,3-dimethylpentane is?

The maximum no. of isomers (including stereoisomers) that are possible on mono-chlorination of the compound: 3,3-dimethylpentane is? The answer given is 5. My working: The fourth carbon is chiral ...
0
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0answers
21 views

Which has a high melting point, cocoa powder or cocoa butter?

I have been doing some research into chocolate, and after looking at the chemical compositions of cocoa butter and cocoa powder, struggled to determine which had a formula/structure that would have a ...
0
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1answer
44 views

mechanism in bi cyclic compounds

In both cases ring expansion is happening. What is Carbon tri chloride purpose?
0
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0answers
39 views

Addition to conjugated dienes

$$\ce{CH2=CH-CH=CH2 ->[\ce{H2/Pt}][\pu{1 equiv}] ?}$$ I thought $\ce{H2}$ should add to one of the π bonds and form but-1-ene. But the answer is but-2-ene. I couldn't understand this.
1
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2answers
82 views

How do α,β-unsaturated acids undergo decarboxylation?

I know the concerted mechanism for β-keto acids, but neither could I figure out, nor was I able to find out the mechanism for α,β-unsaturated acids. Any help is appreciated.
0
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1answer
32 views

Oxidative cleavage of styrene

I could understand that $\ce{-CH=}$ gets converted to $\ce{-COOH}$ and $\ce{=CH2}$ gets converted to $\ce{CO2 + H2O}.$ But I couldn't understand why the double bonds in benzene ring were not cleaved.
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0answers
26 views

Ozonolysis of 1,2,3,4,5,8‐hexahydronaphthalene

Consider 1,2,3,4,5,8‐hexahydronaphthalene: If one equivalent of ozone is added, then which double bond will undergo ozonolysis? If it attacks the more electron rich one, then unstable 10 membered ...
0
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1answer
24 views

Glucose spatial arrangement

It was written in my textbook that the spatial arrangement of hydroxy groups was determined by Fischer by studying certain properties. But I wanted to know to how the relative configurations of ...
0
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0answers
19 views

Number of hyperconjugative structures in aromatic systems

I know that to find the number of hyperconjugative structures in aliphatic systems we use the formula $a + 1$ (where $a$ is the number of α-hydrogens in that compound) However, my teacher answered ...
1
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0answers
26 views

Why is the nucleophilic substitution of OH- with 1-bromopentane slower than with 2-bromo-2-methylbutane?

Which statement about the reaction of a hydroxide ion with the organic reagent is correct? A. 1-bromopentane predominantly follows an $\mathrm{S_N1}$ mechanism. B. 2-bromo-2-methylbutane ...
0
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1answer
32 views

Difference of Ascorbic acid dissolved or precipitated in Glycerol?

Difference of Ascorbic acid (AA) dissolved or precipitated in Glycerol? Referring to pat US20110008445A1 Solution 1 At 25C, AA was dissolved in glycerol and alcohol (subsequently removed by ...
1
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1answer
70 views

Does 2-chloro-1,3-dinitrobenzene show resonance?

I am preparing for my exam, and then I stuck up here. The answer to this question given by my teacher was No, this doesn't show resonance because there are two bulky groups alongside chlorine, due ...
0
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0answers
38 views

Is there any red dye that will work with perflurocarbons?

I have a perflourocarbon (PFC) that I am trying to dye a light red. Is there any way for this to be possible or a specific dye that works with the PFCs?
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1answer
31 views

Which carbocation from following is stable by hyperconjugation?

These are the 4 figures, how to tell which one of them is stable by hyperconjugation? A B C all are stable by resonance if im not wrong but which one is by hyperconjugation too?
2
votes
1answer
36 views

Stereochemical dichloride treatment [duplicate]

In this question there is no inversion in A to B, but there is one in C to D. I feel like this must be due to the lone pairs on the $\ce{S}$ (in A) being able to open the ring, whereas this isn't ...
1
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2answers
38 views

How would this reaction look like in a potential energy diagram? (SN1 Reaction)

My task is to explain, why molecule A reacts in a SN1-reaction faster than molecule B. (I would do this by comparing their potential energy diagrams) My idea is to have a closer look at the reaction ...
-1
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0answers
37 views

Why doesn't Grignard react with THF (when used as solvent) [duplicate]

So on adding Grignard Reagant to an epoxide (3 membered oxirane ), it attacks the electrophilic carbon, but when we dissolved Grignard in THF, Gringard doesn't attack THF (another cyclic ether). Why??
0
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0answers
9 views

Does Hydroboration oxidation always give Anti-Markonikov product? [duplicate]

Consider the case of pent-2-ene, what will happen if we make this compound undergo hydroboration oxidation? I tried this by checking stability of partial positive charge developing on the carbon in ...
1
vote
1answer
36 views

Consequences of ortho effect on resonance

Consider any carboxylic acid with any group at ortho position. According to ortho effect, the resonance of the $\ce{C=O}$ with the ring is inhibited. Is this resonance entirely lost? Or some little ...
3
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0answers
34 views

Procedures for Syringe Pump and organometallic solution

For dispensing a pyrophoric organometallic acid into a reactor under argon flow, is it permissible to place the loaded syringe (glass 10ml, 9ml solution) on the syringe pump, with a long needle (36" ...
0
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0answers
30 views

Retention of configuration in Hofmann rearrangement

Why is there a retention of configuration in Hofmann bromamide degradation/Hofmann rearrangement? I would think that there should be an inversion of configuration due to the migration of alkyl group ...
1
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1answer
37 views

Could an ester react with magnesium oxide?

Esters undergo saponification in the presence of hydroxides. Assuming anhydrous conditions, would they react with magnesium oxide?
5
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3answers
695 views

Why does the -OH group in β-naphthol direct the incoming diazonium salt towards the ortho position? [duplicate]

In the following reactions, the major product W is I was doing this question which asks me the product of a diazotisation coupling reaction between diazonium chloride and β-naphthol. I know ...
0
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0answers
47 views

How to effectively get rid of 2-propanol acetate vapors and smell

I need to get rid of 2-propanol acetate vapors and its smell and need some chemistry help. Some possibilities I came up with: soap and water to rinse surfaces because soap might help increase its ...
1
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1answer
47 views

Is the phenyl group in benzophenone electron donating/withdrawing?

The ketone carbonyl group is less reactive to nucleophilic attack than aldehyde since the alkyl group in ketone is electron-donating towards the carbon. Is this the same case for benzophenone, where ...
1
vote
1answer
71 views

Reaction of 1 equivalent of Mg in ether with 1,4-dibromobut-2-yne

What will be the product formed the if the reaction of Mg in ether with 1,4-dibromobut-2-yne occurs? At first, I thought the answer would be cyclobutyne, but the correct answer is buta-1,2,3-triene. ...
0
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0answers
36 views

Does a non-chiral substrate (2-bromo-2-methylpropane) also form two products via an SN1 mechanism?

If I have an alkyl halide, in which its tertiary carbon is non-chiral (for example 2-bromobutane), which reacts via an SN1 mechanism does it also produce 2 products? I am asking because I know that ...
0
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1answer
56 views

Elimination of hydroxyl group while deprotecting acetal

Regarding this reaction, other than de-protecting the acetal, will we have an elimination reaction for the alcohol or no?
2
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1answer
62 views

Could sodium in ethanol reduce amides to amines?

Strong reducing agents like $\ce{LiAlH4}$ can reduce amides to amines. Sodium in ethanol (as a source of protons) is also a very strong reducing agent. Could it be therefore used to, for example, turn ...
2
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0answers
26 views

Fehling's solution - What is the shelf life of the unmixed A & B components?

If you prepare two separate solutions of Fehling's A and Fehling's B, what is the shelf life likely to be? Will the effectiveness of the solution diminish over time? The literature recommends ...
0
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0answers
44 views

Why F- is more stable than CH3-

When I was reading Organic textbook, I saw a statement of 'F- is more stable than CH3- because the F has a greater electronegativity'. I agree with the explanation 'because of its high ...
0
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2answers
68 views

Why are triple covalent carbon to carbon bonds drawn linearly in skeletal structure? [duplicate]

In the link see that cyclic C-C structure with a triple covalent bond is drawn with an angle, probably the only way to draw it but why is it drawn linearly in non-cyclic and not like single or double ...
2
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2answers
62 views

Rearrangment during alkyne synthesis

What I have got as (G) is this. $\hskip1in$ My questions How the rearrangement from (G) to $non-1-yne$ can happen i.e. its mechanism? Why Sodium Amide in particular yield terminal alkyne, unlike ...
0
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0answers
44 views

decarboxylation of citric acid

1,3 acetonedicarboxylic is very useful in total synthesis of alkaloids. Unfortunately while it can be produced from ubiquitous in plants and convinience stores citric acid, it does require the use of ...
4
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0answers
57 views

An unknown glassware piece from our cupboard

We have multiple of these. It is a small glass funnel with splits into 3 spouts from it. Now, we are thinking it might be similar to a cow receiver, however, I have never seen one this small or ...
4
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0answers
30 views

Unknown possibly handmade glassware- description in information below

Okay, Another random item from the cupboard (unknown users or discipline of life sciences unknown) could be anything up to 40 years old.... This appears to be a 2 neck quickfit adapter (B19 and B14) ...
3
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1answer
25 views

Purification of Solid Phase Synthesized Peptide

I began working in a newly setup lab, and I'm having a dilysine (K2) peptide synthesized by solid phase method. I plan to cleave the peptides from the resin with a cleavage cocktail of TFA. ...
1
vote
1answer
42 views

Reverse Cannizzaro reaction to make aldehydes?

Is it possible (and practicable) to reverse Cannizzaro reaction (disproportionation of aldehydes to carboxylic acids and alcohols) to produce aldehydes from carboxylic acid and alcohol without need to ...
4
votes
1answer
55 views

Butanone or butan-2-one?

According to IUPAC rules, am I right in assuming that butanone is sufficient, because there's only one possible molecule? I keep noticing butan-2-one, so I want to make sure.
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1answer
45 views

Identifying weaker base

Can you tell me the reason behind the answer to this: Which is the weaker base? (a) o-cresol; (b) Trifluoro-o-cresol. Answer: (b) trifluoro-o-cresol. I'm not a student in any institution. So ...
4
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2answers
1k views

Why when I add jam to my tea it stops producing thin “membrane” on top?

Thin "membrane" is created if I leave cup of tea for hour or more. And it usually sticks to the inner sides of the cup. But I noticed that when I drink tea with jam or syrup then the cup always clean ...
1
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0answers
45 views

What does which compound of this mixture do (Glue)

In school we are told to create an organic glue (edible and non toxic) and the teachers said we won´t get any help because it´s the final project. Can you please tell me which of the compounds of this ...
0
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0answers
49 views

Unknown glassware please help, vshaped with a small bulb on one side, hollow but narrow to both sides!

Looking to try an identify some glassware we have found in a cupboard. This is just the start of it... 1 item here, v-shaped, small bulb but hollow, narrow entrance and exit...
2
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2answers
73 views

Does 4-methylbenzaldehyde give haloform and aldol reactions?

The following question was asked in JEE Advanced 2017: The answers given are option A and B. I was able to get B as the correct answer but A look like the wrong option to me. My approach for ...
0
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0answers
62 views

Resonance forms of deprotonated hydroquinone

What resonance forms stabilize deprotonated hydroquinone? Deprotonated hydroquinone looks like this: Possible resonance forms include: 1 and 2 look reasonable: they don't carry multiple charges. My ...
2
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1answer
48 views

Is the -OCH3 group bulky?

Our teacher told us that $\ce{OCH3}$ is a less bulky group when compared to other bulky groups like $\ce{CH3}$, $\ce{NO2}$ etc. Is this true? If yes, why?
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0answers
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What acids will Sodium Lauroyl Methyl Isethionate yield after hydrolysis? [closed]

As far as I understand, after hydrolysis Sodium Lauroyl Methyl Isethionate will yield sodium, lauroyl and methyl alcohols, and isethionic acid. Meaning lauroyl is referring to the fatty acid alcohol ...
6
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1answer
136 views

Molecular orbitals of the enolate ion

The reactivity of the enolate ion is most frequent explained with reference to its system of $\pi$ molecular orbitals. The image below taken from Wikimedia Commons depicts this system of $\pi$ ...