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
-4 votes
1 answer
68 views

Hydration of alkenes: is phosphoric acid a gas at these temperatures?

Ethene is mixed with steam and passed over a catalyst consisting of solid silicon dioxide coated with phosphoric(V) acid. The temperature used is 300°C and the pressure is about 60 to 70 atmospheres. ...
Cheng's user avatar
  • 494
-2 votes
1 answer
147 views

Why sulfuric acid is used in esterification of alcohol and carboxylic acid anhydride?

I have a question regarding why sulfuric acid is used in esterification of alcohol and carboxylic acid anhydride. I know that in case of esterification of alcohol and carboxylic acid, sulfuric acid ...
Harjot Dhillon's user avatar
-4 votes
2 answers
78 views

Resonance energy of organic compounds [closed]

I was solving a problem in organic chemistry, where I had to find the resonance energy of a compound with some information which was given in the question itself. Basically, what I had to do was, to ...
Anirudh Sharan's user avatar
6 votes
2 answers
355 views

Class vs Functional Group: Imprecise Language?

Alcohols, carboxylic acids, esters, alkanes etc are classes of organic compounds, not functional groups, no? (alkanes contain no functionl groups!) In other words, a class is a type of compound, while ...
Cheng's user avatar
  • 494
-3 votes
1 answer
70 views

do catechol and quinol give iodoform test just like resorcinol?

do catechol and quinol give iodoform test just like resorcinol? as ..in case of resorcinol we do have a active methyl after tautomerization which is highly acidic could some kind of mechanism be ...
Arpit Yadav's user avatar
2 votes
0 answers
67 views

Predict the products of organic reaction sequence

This is a reaction sequence involving alcohols, phenols, halides, alkenes ,alkanes etc , and the task is to identify all the compounds A to E The few things I was able to identify : The compound C ...
satvik's user avatar
  • 21
3 votes
1 answer
100 views

Free-radical addition of bromine to alkene

If light and radical initiators are present, radical addition of $\ce{HBr}$ to alkenes takes place and outcompetes electrophilic addition of $\ce{HBr}$ to alkenes. Why isn't a similar thing same ...
Silenus's user avatar
  • 41
-2 votes
1 answer
35 views

Substructure abbreviations with the SMILES format

I am trying to use the SMILES format for encoding molecules from handwritten logbooks. The molecules often contain abbreviations, such as "Ph" for a Phenyl group. Is there a way to have ...
finlay morrison's user avatar
21 votes
1 answer
4k views

Raw green onions are spicy, but heated green onions are sweet. Why is this?

Raw green onions are spicy, but heated green onions are sweet. Why is this? More specifically; what change in the raw green onion's organic chemicals makes it no longer spicy when the green onions are ...
Young Jun Lee's user avatar
2 votes
1 answer
57 views

Substitution of aryl bromide in synthesis of a chelator

Hello I am currently working on a synthesis of a chelator for the synthesis of a photosensitizer for photodynamic therapy. My instructor wants me to do following synthesis procedure: My problem is, ...
Mäßige's user avatar
  • 276
7 votes
1 answer
686 views

What is the correct IUPAC nomenclature for this compound?

I recently came across this type of compound, and normally, I would follow the rules I've previously learnt, which is to find the longest carbon chain that contains the highest priority functional ...
DeadAndAliveCat's user avatar
-4 votes
1 answer
53 views

Why do lipids decrease in viscosity with increasing temperature? [closed]

Is the answer simply that the carbon bonds break up and that the molecules get smaller?
Emanuel Landeholm's user avatar
1 vote
0 answers
143 views

What reaction products are formed if an unsaturated fat is reacted at 20 - 50 °C with H2O2 of 35 %?

My question is: What reaction products are formed if an unsaturated fat is reacted at ca. 20 - 50 °C with aqueous hydrogen peroxide of ca. 35 %? To find the answer, we can subdivide the question into ...
IV_'s user avatar
  • 251
7 votes
2 answers
786 views

Why is prismane explosive but cubane is not?

So I was reading about polyhedral hydrocarbons, because I dig the topic, and I read (admittedly on wikipedia entries... But they cited papers, I swear!) that prismane is explosive due to the massive ...
urquiza's user avatar
  • 711
-3 votes
1 answer
105 views

Can glycerol in substituted natural fats be a monomer according to European REACH Regulation? [closed]

European REACH regulation for registration of chemical substances has an own definition of a polymer according to this regulation. I've noticed the following problem. I want to discuss here only the ...
IV_'s user avatar
  • 251
9 votes
2 answers
897 views

Why is there inconsistency about integral numbers of protons in NMR in the Clayden: Organic Chemistry 2nd ed.?

I was studying the 1H NMR chapter of Clayden: Organic Chemistry 2nd ed. until I came across this case and became curious about integral numbers of protons because it didn't seem right. Then I measured ...
PhenylAmir's user avatar
-4 votes
1 answer
142 views

Common name of CH2Cl2 [closed]

My book says geminal dihalide or alkylidene halide is the common name for dihaloalkanes where both halogen atoms(if of same element) are bonded to the same carbon atom and alkylene dihalide if 2 ...
Nipun Kulshreshtha's user avatar
0 votes
1 answer
150 views

Why can't ethoxide ion act as nucleophile?

Consider the reaction of chlorocyclohexane with ethoxide in a suitable inert solvent. The major product according to my textbook is cyclohexene, which implies E2 reaction pathway. Why not SN2? $\ce{...
Leibniz-Z's user avatar
  • 208
1 vote
1 answer
121 views

Is there any reason why KMnO4 for TLC is stored under basic condition?

my mentor told me that the KMnO4 solution specifically for TLC has added some bases like sodium hydroxide but we don't know why. I try to search on google, and found that the bases are usually by-...
organicrab55's user avatar
2 votes
1 answer
89 views

Mechanism for synthesis of neopentyl iodide using triphenylphosphite/methyl iodide

I was wondering how the reaction between neopentyl alcohol and triphenylphosphite/methyl iodide looks like from a mechanistic point of view. It should involve the formation of a phosphonium iodide ...
Mäßige's user avatar
  • 276
4 votes
1 answer
168 views

Why is more than one product formed in Swarts Reaction?

I have got a very clear idea about Swarts reaction for monohalo compound. But I found the following reaction in Chrome Now, my question is why are 2 products formed? Secondly why is there no ...
Sarban Bhattacharya's user avatar
-1 votes
1 answer
64 views

Boiling point of 2-methylpyridine is less than that of 3-methylpyridine? [closed]

As I was reading about physical properties of pyridines and substituted pyridines, I came across this: 2-methylpyridine boils at 129°C while 3-methylpyridine boils at 15° higher than 2-methylpyridine ...
Natasha J's user avatar
  • 249
1 vote
0 answers
57 views

Esterification of Serine

I came across this question above, and I'm unsure about the reaction with H+(aq). The answer is that the amine group is protonated as usual, but I am not sure why H+(aq) doesn't catalyse ...
George Decesare's user avatar
-3 votes
1 answer
102 views

How many aldehydes and ketones can be formed from molecular formula C5H10O? [closed]

Question: What are the possible aldehydes and ketones with molecular formula $\ce{C5H10O$ (including the stereoisomers)? Answer: 5 aldehydes and 3 ketones The degree of unsaturation of the compound ...
Prithuj Sarkar's user avatar
1 vote
2 answers
109 views

Organic solvents distillation for purification

I've realised that the majority of the solvent that we use in my lab are contaminated with grease (peaks at 1.26 and 0.86 ppm in $^1H$ NMR in $CDCl_3$), since they come in plastic containers (I guess ...
Daniel Álvarez's user avatar
1 vote
0 answers
25 views

When a 7-membered ring is formed during GC/MS, does the substituent need to start with a carbon?

When looking at the GC/MS for Allylthiobenzene aka allyl phenyl sulphide, two clear peaks are seen at 91 m/z and 65 m/z, most common for 7 membered and 5 membered carbon rings respectively. The ...
anonymous plz's user avatar
3 votes
1 answer
107 views

Dipole moments of trans and cis nitrous acid

I have a paper due about the isomers of nitrous acid, using various calculations methods to find molecular properties like their dipole moment. I've found the dipole moment of trans isomer to be 1.987 ...
silvermacabre's user avatar
-3 votes
2 answers
116 views

Confusion in n factor in the reaction [closed]

What will be the n-factor of $\ce{O2}$ in the reaction: $$\ce{C4H10 + \frac{13}{2} O2 -> 4 CO2 + 5 H2O}$$ My tutor said it will be 26 but I am confused because he used stiochiometric coefficients ...
Nishchal123's user avatar
3 votes
0 answers
35 views

How do polyurethane varnishes cure after only the solvent evaporates

How do polyurethane varnishes cure after only the solvent evaporates? I believe that polyurethane varnishes have as components isocyanates & polyols that react to form the polyurethane portion of ...
Tempus Nomen's user avatar
-1 votes
1 answer
92 views

Hydration of alkenes [closed]

In the image I've provided, I offer two alkenes. The first is in conjugation while the second isn't. Additionally, both of the C=C groups are symmetrical, in the sense that they both have one hydrogen ...
b20's user avatar
  • 11
0 votes
1 answer
48 views

What nucleophilic reaction takes place in case of bad leaving group as well as 1* alpha carbon?

If we add HI to a substrate Ph-C-C-OH what will be the major product and what reaction mechn. will be followed? My attempt: as -OH is bad Leaving Group, we cannot just simply proceed with Sn2 and ...
Ash_Tag's user avatar
  • 23
-1 votes
1 answer
62 views

Reaction Order from Percent Yield?

Referencing this paper, I am trying to approximate the order of reaction for cyclohexane (4a). Trials 1-3 provide the relevant information of mmol changes and corresponding percent yield but I'm ...
Boris Tangerine's user avatar
5 votes
2 answers
667 views

Does Grignard reagent on reaction with PbCl2 give PbR4 and not PbR2?

I was told by my teacher that $\ce{RMgX}$ forms $\ce{PbR4}$ when it reacts with either $\ce{PbCl2/PbCl4}$ the later case is clear to me but why does $\ce{PbCl2}$ forms a compound of the form $\ce{PbR4}...
Ayush Upadhyay's user avatar
1 vote
0 answers
75 views

Does heating 3-phenylpropionic acid decarboxylate it?

Here, when P is reacted with $\ce{SOCl2}$ and then NaCN to give 3-phenylpropionitrile and then hydrolysed to give 3-phenylpropionic acid. Why shouldn't it further decarboxylate and dehydrogenate to ...
Fighter's user avatar
  • 21
1 vote
1 answer
568 views

Different types of bond representations [duplicate]

What do the following different kind of bonds mean? Although this answer to the question "What are the meanings of dotted and wavy lines in structural formulas?" does describes some of the ...
ananta's user avatar
  • 2,103
4 votes
1 answer
193 views

What are the best conditions for EDC coupling of 2 small molecules?

I want to couple 2 small molecules, one is a DNA oligo with an amine group and the other one a small molecule with with a carboxyl group. I found protocols for EDC (1-Ethyl-3-(3-dimethylaminopropyl)...
Brenlla's user avatar
  • 191
2 votes
1 answer
134 views

Effect of Solvent - Nucleophilicity of RS- and RO-

While reading on order of nucleophilicity of $\ce{RS-}$ and $\ce{RO-}$, I came across this: Source: Page 355, Organic Chemistry by Jonathan Clayden, Nick Greeves, and Stuart Warren However, my teacher ...
omega's user avatar
  • 47
3 votes
1 answer
92 views

Glutaraldehyde or Glutardialdehyde

Recently I was searching for a chemical compound to meet my research needs, i.e. glutaraldehyde, and later I found that Merck has been released different name of compound: (1) glutaraldehyde and (2) ...
Muhammad Ihsan's user avatar
-4 votes
1 answer
339 views

why does -CHO hold higher priority over -CH2OH according to CIP rule [closed]

i am unable to find proper resources to learn CIP rule at a high school level withut delving deeper into terms i cant understand and hence the basic confusion.if i am correct one has to first compare ...
Karan's user avatar
  • 73
3 votes
1 answer
156 views

Why does Alcohol-Dehydrogenase prefer ethanol over methanol?

So I've had this experiment at university, where we tried using (yeast) ADH on different alcohols and measuring which one gets turned over the fastest. We also learned that ADH prefers shorter ...
m0n74g3's user avatar
  • 33
2 votes
2 answers
427 views

What is the pH of acetone in water?

Reaction of Acetone with Water Acetone in water can react in three ways: The different reactions change the concentrations of $\ce{H+}$ and, consequently the pH, differently. My question is what is ...
ananta's user avatar
  • 2,103
1 vote
0 answers
53 views

What is the best way to draw chemical structures in LaTeX? [closed]

I was just wondering what the best option is for getting chemical structures/reactions in LaTeX. Should I just draw the molecule in ChemDraw/ChemSketch then export it to LaTeX or is there a particular ...
dlsloop's user avatar
  • 31
2 votes
0 answers
37 views

Have I named this compound correctly using IUPAC naming conventions?

I think it is 3-[3-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]-R-phenyl]-4-Ar. But I'm not sure and would really appreciate some help
Yatharth P.'s user avatar
-2 votes
1 answer
59 views

Neighbouring Group Participation of Aldehyde group

Does the aldehyde group -CHO give neighbouring group participation? For example in the following compound: Why or why not will the formyl group show neighboring group participation? Although I have ...
omega's user avatar
  • 47
1 vote
2 answers
85 views

Why does this show E1CB mechanism?

The following is a solution to a "match the following" question from IITJEE 2006. I'm confused why does it show E1CB mechanism? Isn't the mechanism exclusively for highly acidic Hydrogen ...
Arghya Shubhshiv's user avatar
0 votes
0 answers
34 views

Will alcoholic acid solution with organic acids break down Bakuchiol and reduce it's biological effect?

I wish to use Bakuchiol in a solution of isoproply alcohol and water in the presence of glycolic acid (7%), citric acid (0.5%) and salicylic acid (1.4%) at a pH of 4 to 5, adjusted with TEA. Wu et ...
Simon Hales's user avatar
0 votes
0 answers
40 views

Enamine formation mechanism. Can't there be alternatives?

I'm studying organic chemistry, more specifically the imines and enamines. I've read about the mechanism of formation of enamine from a generic ketone and a question popped up in my mind. The ...
Paolo Larocca's user avatar
3 votes
1 answer
393 views

Why does N,N-dimethylethanamide have a higher boiling point than butanoic acid?

According to Wikipedia, N,N-dimethylethanamide has a boiling point of $\pu{165.1 °C},$ while butanoic acid has a boiling point of $\pu{163.75 °C}.$ From what I learned, butanoic acid should have a ...
Pen and Paper's user avatar
-2 votes
2 answers
321 views

How much can we extend the Finkelstein reaction?

Finkelstein reaction explicitly entails the conversion of an alkyl chloride or alkyl bromide to alkyl iodide by treatment with sodium iodide in acetone. $$\ce{R−X + NaI→[acetone] R−I + NaX↓ }\\ \ce{(X$...
D13G's user avatar
  • 89
-3 votes
1 answer
50 views

Difference between ketone rings in wavelength using an IR device [closed]

It is said that the smaller the ring size, the greater the wavelength of the carbonyl group, but why does cyclobutanone have a higher wavelength than cyclopropanone?
Jeje Saad's user avatar

1
3 4
5
6 7
205