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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.

3
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1answer
42 views

NMR analysis regarding cis-1-isopropyl-3-phenylcyclohexane

I have come across a question in my textbook: The textbook gives this answer: I understand the explanation for the first compound. However, for the second structure, I am not understanding why the 2 ...
3
votes
2answers
173 views

Are there amide versions of lactides and lactones?

In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $\alpha$-hydroxy; and $\gamma$- or $\delta$- hydroxy ...
1
vote
0answers
19 views

Do acid derivatives (anhydrides/amides/acyl halides) give positive Iodoform test? [closed]

Technically, having a methyl carbonyl group should enable them to give positive Iodoform test.
0
votes
1answer
62 views

questions about the synthesis of iodobenzene from aniline

I am conducting an experiment about synthesis of iodobenzene from aniline, referring to this site(and various sites) (http://www.prepchem.com/synthesis-of-iodobenzene/). Below is my experimental ...
0
votes
1answer
74 views

Which one is the stronger base?

I'm studying Wolff-Kishner reduction and I don't understand why after this step the leaving group is $\ce{OH-}$ instead of $\ce{^-HN-NH2}$. I guess it's because hydroxide ion is less strong than the ...
-2
votes
1answer
91 views

hydrogenation using H2 + Ni2B [closed]

I am having trouble understanding why hydrogenation with $\ce{Ni2B}$ gives anti-addition. all my book says is this: Could someone explain the mechanism.
0
votes
1answer
42 views

Is benzenesulfonic acid or cyclohexanesulfonic acid more acidic?

Which of the two sulfonic acids above is a stronger acid? I think that cyclohexanesulfonic acid 2 should be more acidic as there is no competitive resonance as in 1. Is that correct?
-1
votes
1answer
33 views

What is the solubility of quinine suphate in 98% ethanol?

I have a result from an experiment that really bothers me, yet I found no sources online that can explain the situation. While quinine is relatively soluble in ethanol because they are both non-...
-1
votes
0answers
31 views

Question related to KMnO4

Why in acidic medium $\ce{KMnO4}$ oxidizes $\ce{KI}$ ($\ce{I-}$) to $\ce{I2}$ but in alkaline medium to $\ce{IO3-}$? $\ce{KMnO4}$ is a stronger oxidising agent in acidic medium then why doesn't it ...
-1
votes
1answer
7 views

Where will the positive charge shift in the E1 mechanism of dehydration of an alcohol? [closed]

My Attempt: according to me the double bond should be in position no. 2 but the correct answer has a double bond in position no.1. Why is it so? Thanks in advance.
0
votes
1answer
57 views

Can aromatic rings be cyanated using cyanide as a nucleophile? [closed]

For example, can I convert chlorobenzene into benzonitrile by using potassium cyanide as the reagent?
0
votes
0answers
27 views

Electrophillic Iodination

I read that the Iodination of C6H6 (in presence of FeCl3) has a higher rate constant than C6D6 (in presence of FeCl3) in a book. It has mentioned without much explanation by simply stating that its ...
-1
votes
1answer
19 views

What is the condensed formula of 2-phosphoglyceric acid?

I'm looking for a simple way to visualize the position of the phosphate on 2-phosphoglyceric acid. The condensed formula seems like the best way to do this because it omits the shape of the molecule.
6
votes
1answer
45 views

How does this ring expansion on a steroid system occur?

The correct answer is supposedly B, as shown by Gravestock et al.[1] In this reaction after ozonolysis of the C=C double bond, two ketones are formed. How is a rearrangement or expansion of the ring ...
7
votes
0answers
69 views

Is the 9H-fluoren-9-ylium cation aromatic?

In this cation, there are two individual benzene rings which are aromatic. But in the entire π system, there are 12 π-electrons which should make it antiromatic. Which is correct?
-1
votes
1answer
12 views

Properties of food in different states [closed]

I've gotten into a heated discussion over the topic of foods before and after they have been cooked and or mixed. My opinion is that the properties obviously change once either mixed or exposed to ...
2
votes
1answer
54 views

Use of axis of symmetry

Does an axis of symmetry determine chiralty? Is axis of symmetry considered a true symmetry? From the above two links, I read that a compound having axis /alternating axis of symmetry is NOT ...
1
vote
1answer
73 views

Most reactive site for electrophilic aromatic substitution

I was given a problem in which I had to identify the most reactive site for electrophilic substitution out of the positions 1,2,3,4 (shown in the figure). My Approach: Upon drawing the resonating ...
-1
votes
1answer
24 views

Fischer Projection

i'm confused of how to get the Fischer projection of the molecule on the top. i can see that the hydrogen and OH group are sticking out. However i don't understand how the CH2OH group is pointing ...
1
vote
0answers
34 views

What is the purpose of tetrazole in oligonucleotide synthesis?

The ATDBio book on nucleic acids describes tetrazole as an activator required to couple nucleotides. The diisopropylamino group of the nucleoside phosphoramidite is protonated by the activator, ...
-1
votes
1answer
23 views

Organic reduction of alkene

Can Wolff Kishner and Clemmensen Method be used to reduce alkyne or alkene. If so do they produce syn addition or anti addition product. ?
2
votes
1answer
82 views

Can bridged and bridgehead positions be chlorinated using free radical mechanism?

When the above compound is treated with $\ce{Cl2}$ in the presence of sunlight ($h\nu$), what is the number of monochloro structural isomers formed? I expected only 1 product becuase I don't believe ...
-1
votes
0answers
57 views

PCl5 with glycerol

The major product given for the reaction is 1,3 dichloropropane but why stop there? Why dont we get 1,2,3-trichloropropane the only reason i can come to justify this is steric protection by Cl. ...
-1
votes
0answers
12 views

nommenclature of organic compound [duplicate]

***1,1,1- trichloro -2,2-bis(4-chlorophenyl)ethane*** our chemistry teacher gave this name to given organic compound why not we can write it as ...
-1
votes
1answer
54 views

Which is more acidic - 3,5-dimethylphenol or 3,5-dimethyl-4-nitrophenol?

Does steric hinderance stops the benzene ring resonance?
5
votes
1answer
99 views

What chemicals have been named after Star Wars characters?

The molecule below is whimsically named Yoda1 because it "uses the force" to open channels in a class of animal proteins known as piezo ion channels (which appear to be part of their pressure sensing ...
1
vote
1answer
52 views

Why does CH3CH(OH)CH2CH3 give iodoform test?

The iodoform test is given by compounds containing $\ce{-(C=O)CH3}$ group or compounds which can be oxidized to such. $$\ce{ CH3CH(OH)CH2CH3}$$ Is a 2 degree alchohol and even though it were to be ...
-1
votes
2answers
44 views

Feasibility of Electrophilic attack on the Nitrogen over the Phenyl ring of Aniline

I have learnt that the '-NH2' substituent attached to the phenyl ring, owing to the substitutent's highly positive mesomeric effect, activates the phenyl ring quite a lot for Electrophilic Aromatic ...
0
votes
1answer
37 views

How can iodized oil be made?

I want to combine solid elemental iodine with olive oil, to form an iodized oil - what is called an iodostearic acid or iodooctadecanoic acid, here the double bond in the oil becomes saturated by ...
-1
votes
1answer
52 views

A problem on stability of carbanion

Determine the most stable of the two carbanions. I found second one as more stable because of inductive effect. But the given answee is first one.
-2
votes
1answer
63 views

On the stability of carbocations

I have a question regarding the stability of carbocations. It is shown below. I am confused between options II and III. The structure shown in option II has more resonance structures. Thus, I ...
0
votes
1answer
40 views

Does resonance destabilize a molecule?

According to this table, more heat is released in breaking a single double bond in 1,3-butadiene than in trans-2-butene. Does this mean that the resonance of 1,3 butadiene leads to a destabilization ...
1
vote
1answer
73 views

Elimination reactions of vicinal dibromide

When a vicinal dibromide undergoes elimination reactions in vigorous basic conditions, say in ammonia with $\ce {NaNH2}$, is the product an alkyne or is it a conjugated diene? I would think that the ...
0
votes
0answers
31 views

Why don't zwitter ions show ortho effect?

I recently came across a statement which said that zwitter ions are an exception to the ortho effect. Is it because the ions attract each other and the -COOH group is brought back into the plane ...
-1
votes
1answer
73 views

How does hyperconjugation explain the stability of alkenes?

The more the number of alpha hydrogens, the higher is the stability of alkenes, because the more the number of hyperconjugative structures. Why is this so? Has it got something to do with the ...
0
votes
1answer
35 views

Rearrangement of anions [duplicate]

My book says a. But i think it is wrong. Rearrangement is not possible in anion me, ans also there is group migration but here the group has been divided .
1
vote
0answers
28 views

Xylene leaves a stain after evaporating?

I'm using xylene to clean a sacrificial polymer layer off of a PMGI surface in a ventilated hood. For some reason, when xylene dries naturally from the surface there is a liquid stain that can be ...
0
votes
1answer
42 views

Wittig reaction with an alkyl dibromide

Recently, I have come across a problem, in which a ketone needs to be converted into an alkene. However, in the alkene product, there is also another bromide functional group, at the end of the alkyl ...
2
votes
0answers
21 views

What is correct cyclopenta[a]phenanthrene numbering?

IUPAC BlueBook 2013 states: P-25.3.3 Numbering fused ring systems Fused ring systems with retained names, systematic names, or fused names are systematically numbered in the same manner. ...
0
votes
0answers
12 views

Why absorption changes in schiff-base formation? Coenzyme PLP

Pyrodoxal-5-phosphate (PLP) in enzymes form schiff-base to lysine residue. This can be detected by the change in the absorption from 390 nm to 420 nm (free PLP to stiff-base bound PLP). I remember ...
1
vote
2answers
31 views

Why does the alkaline hydrolysis of benzamide yield ammonia?

Nucleophillic addition to the carbonyl group is governed by the rule that a less basic group is displaced by a more basic group since $\ce{NH2^-}$ is more basic than $\ce{OH-}$ the reaction should not ...
3
votes
1answer
68 views

Regioselectivity in Diels Alder reaction

Since $\ce{-CN}$ shows strong $\ce{-I}$ effect, there will be $\delta +ve$ charge on the carbon adjacent to it. Similarly, $\ce{-NO2}$ shows strong $\ce{-I}$ and $\ce{-M}$ effects. So I this is my ...
2
votes
1answer
73 views

Why is hexane called skellysolve-B

https://pubchem.ncbi.nlm.nih.gov/compound/hexane Another name for hexane is skellysolve-B, is that just to be silly?
3
votes
1answer
107 views

How does base size affect the ratio of kinetic/thermodynamic enolate?

One of the factors that favor kinetic products is bulky bases. So, I'd expect that, for a certain substrate, the use of a more bulky base to favor even more the kinetic product. However, in the table ...
0
votes
0answers
44 views

Effect of H-bonding on o-nitrobenzoic acid

My argument here is regarding the acidity of o-nitrobenzoic acid being greater than p,m-nitrobenzoic acid. In o-nitrobenzoic acid, there is an intramolecular hydrogen bond which makes the bond ...
1
vote
1answer
78 views

Stability between benzyl free radical and tertiary free radical [duplicate]

My teacher told me that the hyperconjugation of 9 alpha hydrogen domintes over resonance (for a carbocation )and so the stability of a tertiary carbocation is more than benzyl carbocations due to ...
0
votes
0answers
36 views

Why Isn't Huckles rule applicable to more than 3 fused rings [duplicate]

In the following compound (Pyrene) why isn't Huckle's (4n+2) rule applicable? I do know it is applicable to only mono-cyclic ring systems but what changes when there are more than 3 fused rings? ...
0
votes
1answer
80 views

Alcohol protection with ethers

Various ethers are used for hydroxyl protection. My question is about their removal. I know that there are various methods but I want to specify on the use of acids. Certain groups are removed easily ...
0
votes
1answer
44 views

What are solvents that can dissolve sebum that is safe for topical use? [closed]

I do not know much about these properties and I need some feedback regarding these. Sebum is a semi-fluid that in humans contains a mixture of triglyerides, cholesterol, ester waxes, and squalene. 57....
1
vote
0answers
61 views

Mechanism of Dow's process

Does Dow's process follow Benzyne mechanism or ArSn2 mechanism?In some books I have seen that Dow's process to convert halobenzene to phenol follows ArSn2 mechanism.But nucleophilic substitution in ...