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.
10,201
questions
-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.
...
- 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 ...
- 110
-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 ...
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 ...
- 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 ...
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 ...
- 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 ...
- 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 ...
- 117
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 ...
- 421
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, ...
- 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 ...
- 183
-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?
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 ...
- 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 ...
- 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 ...
- 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 ...
- 93
-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 ...
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{...
- 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-...
- 11
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 ...
- 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 ...
-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
...
- 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 ...
-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 ...
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 ...
- 330
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 ...
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 ...
-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 ...
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 ...
- 149
-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 ...
- 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 ...
- 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 ...
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}...
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 ...
- 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 ...
- 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)...
- 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 ...
- 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) ...
-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 ...
- 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 ...
- 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 ...
- 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 ...
- 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
- 21
-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 ...
- 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 ...
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 ...
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 ...
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 ...
- 211
-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$...
- 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?
