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.

Filter by
Sorted by
Tagged with
0
votes
0answers
16 views

What exactly is an 'activated' alcohol? Benzylic vs. Allylic vs. Aliphatic

I'm currently writing a report about the oxidations of various alcohols using different catalytic systems. In all papers it is stated that benzylic and allylic alcohols are "activated", while ...
0
votes
0answers
23 views

What factors affect the chemiluminesnence of a glow stick reaction?

I know that temperature affects the reaction rate of a glowstick, but are there any other factors? I was thinking the different color dye molecules would have an effect on the reaction rate, since ...
1
vote
0answers
24 views

How can we calculate the “degree” of conjugation?

So a conjugated system is a system of connected p orbitals or alternating single and multiple bonds. I know that conventionally, we count the number of adjacent parallel p orbitals or alternating ...
4
votes
2answers
267 views

Selective reduction of nitro group to amine, in benzene ring containing nitrile?

I would like to know if there is a possible route of synthesis that may reduce the shown compound A to the following product B. I would normally reduce a nitro to an amine using $\ce{Pd/C}$ and $\ce{...
0
votes
1answer
30 views

How will the degree of conjugation effect the light emitted? (glow stick reaction)

So regarding the chemiluminescence in a glow stick reaction, the glow is due to the unstable compound 1,2-dioxetanedione decomposing into carbon dioxide, releasing energy which is then absorbed by the ...
1
vote
0answers
19 views

which oxygen atom make intramolecular hydrogen bond in salicyclic acid?

When I googled about intramolecular hydrogen bonding in Salicylic acid, I found that there are two type of hydrogen bonding. Which one is more appropriate? And another question, if there ARE two ...
2
votes
1answer
31 views

How do Lewis acids interact with 1,4-diketones and amines to form an alkaloid?

The following double cyclization was used to generate the ring system of the lycoanitine alkaloids in 2005. Demonstrate your understanding of this C−C bond-forming process by providing a mechanistic ...
0
votes
0answers
12 views

Why homolytic fission of polar molecules is possible at higher temperature?

While studying alkanes I came across the nitration of alkanes using Nitric acid at very high temperature, which apparently follows "free radical" mechanisms, by formation of OH° °NO2 free radical ! ...
-1
votes
2answers
40 views

Why does a substance such as methane have 4 sp3 orbitals rather than 3 orbitals [closed]

I have been learning about SP3 hybridisation and slightly confused why it it results in 4 sp3 orbitals. My understanding is this... The S orbital is spherical and uniform whilst the p orbitals are ...
1
vote
0answers
33 views

Fischer Esterification of the Unsaturated 3-Butenoic Acid with Methyl Alcohol

I am attempting to perform a Fisher esterification of 3-butenoic acid (vinyl acetic acid). I believe that this should theoretically work and not disturb the unsaturated region of the molecule, but I'm ...
1
vote
0answers
27 views

Confused about identifying delocalized electron pairs in Isoniazid

I have to identify delocalized electron pairs in Isoniazid (pairs not shown in the image below): I know the nitrogen in the ring has a localized electron pair, since it already forms a pi bond. I'm ...
0
votes
0answers
21 views

Benzannulation of 18-crown-6

I know crown ethers can be used to complex metal ions. Question: What important properties do 18-crown-6 change during the benzannulation from 18-crown-6 to DB18C6 (dibenzo-18-crown-6)? How do these ...
1
vote
1answer
19 views

Properties of starch in packaged pudding

I had a mug of packaged pudding. The top layer of the pudding was of typical pudding consistency, while the bottom was more runny. What could have caused this?
0
votes
1answer
42 views

What will be the name of CH2=CH-O-CO-CH3?

We have this question in the textbook but there is no answer given and I have no idea how to name this compound. Edit: I tried naming the compound. Correct me if I am wrong here 1-Methylpropenoate
0
votes
1answer
48 views

Nucleophillic addition reaction in the presence of an acid catalyst on a molecule with an alkene

This is a solution for a question in my textbook. In the presence of an acid catalyst, am I wrong in my understanding that the acid will protonate the alcohol, and then do an electrophillic addition ...
2
votes
0answers
44 views

Do tertiary ethers tolerate oxidative workup of an ozonolysis reaction?

I am attempting to cleave a double bond into a carboxylic acid and carbon dioxide using an ozonolysis reaction followed by an oxidative workup. I am concerned with the presence of a tertiary ether in ...
4
votes
1answer
103 views

Reduction of amino acids to corresponding amino alcohols

I've stumbled upon an interesting article about reduction of amino acids and from there to reduction of L-valine to L-valinol using $\ce{LiAlH4}$ in THF. Article says that because of the cost of $\...
-4
votes
1answer
48 views

Best method to increase the chain length of allyl to butane-1,2-diol [closed]

Best method to increase the carbon chain length of allyl. and also add 2 OH carbon after reducing double bond give (S)-4-R-butane-1,2-diol and (R)-4-R-butane-1,2-diol . R= Any Ak, Cb, Cy, Hy
1
vote
2answers
185 views

Do SN1 reaction always result in Racemisation

In the following reaction the products formed are not enantiomers but are diastereomoers.So there is no racemisation occured.So is it always correct to say that SN1 result in racemisation?
0
votes
0answers
24 views

How to eliminate formaldehyde including the smell from human hair extensions? [closed]

I was wondering how to get rid of the presence of formaldehyde in clip in hair extensions completely? (They’re human hair). They have a really bad chemical smell at first I didn’t know why and assumed ...
1
vote
2answers
49 views

Is a liquid vitamin E supplement possible without additives? [closed]

Looking at E vitamin products sold commercially, all “pure vitamin E oil” products seem to be for skincare rather than consumption as a supplement. I have read that d-alpha tocopherol is the form of ...
0
votes
1answer
30 views

How to find the volume of the products in methane combustion?

The combustion of methane gas, $\ce{CH4}$, gives as products $\ce{CO2}$ and $\ce{H2O}$, both in the gas phase. If $1$ liter of methane is burned in the presence of $10$ liters of $\ce{O2}$. Suppose ...
0
votes
0answers
16 views

Why a bottle of red wine turns sour after exposed to air for a few days? [duplicate]

I think it is because ethanol will not only oxidized by air commonly.
1
vote
0answers
25 views

Acidity of 2-sulfopropanedioic acid in water

Sulfuric acid is a strong acid ($\mathrm{p}K_\mathrm{a}$ value below that of $\ce{H3O+}$: completely dissociated in water) at its first deprotonation, but is a weak acid ($\mathrm{p}K_\mathrm{a}$ ...
8
votes
1answer
143 views

What is the most acidic neutral hydrocarbon?

This is a question I've been thinking about quite frequently. I had seen that this hydrocarbon has a low $\mathrm pK_\mathrm a$ with reference to the highlighted H-atom Loss of the central gives ...
0
votes
1answer
38 views

Can a compound with indirectly bonded carbon and silicon atoms within the same aromatic system be called organosilicon compound?

Wikipedia says that organosilicon compounds are organic compounds with carbon-silicon bonds. Does the class of organosilicon compounds include compounds in which the carbon and silicon are only ...
2
votes
0answers
22 views

What is the distinction between alkyloxy and alkoxy prefixes, if any?

The IUPAC nomenclature guidelines reference alkyloxy and alkoxy prefixes at different points. Is there any distinction, at the level of a principle or rationale, between the use cases for the two? For ...
-2
votes
1answer
37 views

Can butan-1-ol be written as butanol, and is it connected to butan-1-ol having Isomers? [closed]

Can butan-1-ol be written as butanol, and is it connected to butan-1-ol having Isomers?
-1
votes
0answers
23 views

Acidity of anilinium ion and para fluoro anilinium ion [duplicate]

Which one of anilinium ion and para fluoro anilinium ion is more acidic ? According to me since -F is an electron withdrawing group thus para fluoro anilinium ion should be more acidic . But on ...
1
vote
0answers
29 views

Rate determining step in oxidation of alcohols using chromium-related compounds

I wanted to ask a question about the kinetics of an oxidation reaction using chromium reagents. I was given a lecture today on the mechanism of alcohol oxidations using Chromate (VI) reagents: My ...
2
votes
1answer
49 views

Can we use HPLC to purify an organic reaction product?

I know HPLC is a form of column chromatography that uses high pressure to pump a sample mixture/eluent through a column. However, I'm not sure if this technique is being used to purify and isolate ...
0
votes
0answers
35 views

How to increase the conversion for the reaction between 2-acetylpyridine and diamine?

I tried refluxing in toluene using activated molecular sieves to absorb any water produced (didn't use Dean-Stark trap as it's a very small scale reaction). This reaction isn't going by changing the ...
1
vote
1answer
43 views

Reaction of phenol with concentrated sulfuric acid

What is the product when phenol reacts with conc. $\ce{H2SO4}$ in excess? I have been told that the major product will be ortho at low temperature and para at high temperature. Why cannot it form ...
2
votes
0answers
30 views

Can anyone suggest a mechanism for hemiaminal metal complex to imine complex?

Can anyone suggest a probable reason for this conversion? This seems like a simple conversion from hemiaminal to imine. For secondary amine this kind of conversion might be possible by but in the ...
0
votes
1answer
80 views

Mechanism for reaction of NOCl (Tilden reagent) with primary amines

According to my textbook, the reaction between $\ce{NOCl}$ and $\ce{CH3CH2-NH2}$ is as follows: $$\ce{CH3CH2-NH2 + NOCl -> CH3CH2Cl + N2 + H2O}$$ But how exactly does the reaction proceed? ...
0
votes
0answers
46 views

How does the relative acidity of 2,3-dinitrophenol compare to that of 2,4-dinitrophenol?

I am assuming that the -I inductive effect in 2,3-dinitrophenol is stronger than in 2,4-dinitrophenol since it operates through less bonds, therefore on inductive grounds it should have a lower $\...
0
votes
1answer
30 views

cyclopropane's reaction with lithium aluminium hydride [closed]

what is cyclopropane's reaction with lithium aluminium hydride? I think it must lead to ring-opening but I didn't find any article favoring this in my texts.
0
votes
0answers
33 views

Why do α- and β- Keto acids with Ph groups are generally not reduced,but other keto acids are reduced?

The reactions that I am thinking about: Ph here is for phenyl group I tried to do this by using the nakayabashi mechanism but could not find any resonance structure or anything special.I also thought ...
8
votes
2answers
882 views

Are monosubstituted cyclopropanes achiral or chiral?

A classmate an I were discussing the chirality of this molecule which is a monosubsituted cyclopropane. I argue this is an achiral molecule because that carbon which is bonded to bromine cannot be a ...
2
votes
0answers
24 views

Grignard Reaction with Unsaturated Methyl Ester | Prevention of Acid Catalyzed Hydration

I am attempting to perform a Grignard reaction involving methyl 3-butenoate and methyl magnesium iodide in order to yield the unsaturated tertiary alcohol 2-methyl-4-penten-2-ol. The issue in doing ...
7
votes
1answer
181 views

Meaning of the term “vertex” in the topic of skeletal formulae

From the Wikipedia article on skeletal formula: Hydrogen atoms attached to carbon are implied. An unlabeled vertex is understood to represent a carbon attached to the number of hydrogens required ...
3
votes
1answer
98 views

Product of the reaction between hexane‐2,5‐dione and ammonium carbonate

Which of the following statement is INCORRECT? (A) The product X has a five membered ring. (B) The product X is aromatic. (C) The degree of unsaturation of the product X is 3. (D) The ...
3
votes
0answers
24 views

Formation of intimate ion pair by halogenoalkanes

I was recently doing this organic chemistry question that tested on the concept of the formation of the intimate ion pair in the nucleophilic substitution reaction at an $\ce {sp^3}$ carbon: $\ce {...
1
vote
1answer
55 views

Precipitation of water-insoluble materials from shower or laundry greywater

I am currently working on a project to build a filter that aims to separate or salt out the 'dirt' in shower or laundry greywater. The ideal result from this chemical reaction will be such that the '...
0
votes
1answer
79 views

Is Hoffman elimination anti or syn elimination?

I read an amazing PDF from nptel on elimination reactions...but I was really confused when it used used $\ce{^+NMe3}$ as a leaving group in the reaction pathway via: $\mathrm{Ei}$ (syn-elimination) $...
1
vote
1answer
92 views

Is this a plausible reaction mechanism? (H2SO4 cyclization after Friedel-Crafts)

in my undergraduate chemistry lab we synthesized the substituted benzene on the left in a Friedel-Crafts reaction. As a next step we're supposed to reflux for 1.5h at 90°C with concentrated sulfuric ...
3
votes
2answers
44 views

Acidic strength order in gaseous phase

I got this question in my exam: Arrange the following in increasing order of acidic strength in gaseous phase (i) $\ce{CH3CH2COOH}$ (ii) $\ce{CH3COOH}$ I felt that increasing order must be (i)...
1
vote
0answers
26 views

Counterion exchange

I have a quick question about counterion exchange. I have this very practical problem at my hands that I have a ethyl sulfate $(\ce{EtSO4-})$ counterion for a $\ce{R4N+}$ moiety ($\ce{R}$ = 3 ...
-5
votes
0answers
29 views

Topic- haloarenes

Q27) Out of chlorobenzene, o-methyl chlorobenzene and m-methyl chlorobenzene, which has more affinity for nucleophilic substitution?
-1
votes
1answer
63 views

How does the sec-pentanyl group look? [duplicate]

I'm starting the very basics of hydrocarbons and I'm having a hard time at understanding when to use the common/trivial name prefixes (sec-, iso-, neo-, etc.). One particular problem is the ...