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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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aldehydes are easily oxidised but ketones are not

Aldehydes are easily oxidized to carboxylic acid but ketones are difficult to oxidise. Most books say that the hydrogen directly bonded to the $\ce{C=O}$ in the aldehyde is what aids the oxidation ...
0
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0answers
12 views

Does sodium borohydride reduce C=N group?

Q.15 the major product of the following reaction is: I have read that $\ce{NaBH4}$ reduces only aldehyde, ketone and acid chlorides. In some cases it may reduce double bonds conjugated with ...
2
votes
1answer
70 views

How many stereoisomers can exist for 4,5-bis(3-hydroxyoct-1-en-1-yl)cyclopentane-1,3-diol?

Q.10 For the given compound $\ce{X}$, the total number of optically active stereoisomers is ____. This is from JEE Advanced 2018 second question paper. I thought the answer to be at least 32 ...
0
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1answer
46 views

Reaction of orthocresol with butyrolactone in presence of AlCl3 and heat

What will be the major product of the following reaction? Please also help me with the mechanism. I'm not sure whether C- acylation or O- acylation will occur here. And if O- acylation does occur, I ...
1
vote
1answer
37 views

What is the driving force for Claisen rearrangements?

I came across this mechanism (3,3 sigmatropic rearrangement). Why does the allyl vinyl ether have the ability to rearrange itself giving a new product? What drives the reaction? Is it the instability ...
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0answers
7 views

KINETIC MOLECULAR THEORY [on hold]

Part 1. A chemist reacted 18.0 liters of F2 gas with NaCl in the laboratory to form Cl2 gas and NaF. Use the ideal gas law equation to determine the mass of NaCl that reacted with F2 at 290. K and 1.5 ...
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0answers
17 views

PHASES OF MATTER : KINETIC MOLECULAR THEORY [on hold]

Part 1. A glass bottle, which is half-filled with water, has a balloon attached to its opening. The bottle is placed in a hot water bath for some time. Explain the change to the size of the balloon ...
-1
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1answer
309 views

Reagents to synthesise butanedioic acid from 1,2-dibromoethane

Why can't we use $\ce{HCN (g)}$ and $\ce{HCl (aq)}$ to convert 1,2-dibromoethane into butanedioic acid? I found out that the answer is $\ce{KCN (aq/alcoholic)}$ and $\ce{H2SO4 (aq)}$, I don't ...
0
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1answer
28 views

What do D and L stand for in the Fischer-Rosanoff convention?

In R and S configuration, the R stands for rectus and the S stands for sinister. Similarly, do the D and L descriptors in the Fischer-Rosanoff convention stand for something?
2
votes
1answer
49 views

Why does d/l-2,3-dibromobutane on reaction with NaI/acetone give cis-2-butene?

This is what I have read/know about the dehalogenation of vicinal dihalides by NaI/acetone: The two halides which are leaving must be on opposite sides (from the mechanism). In case they are present ...
-1
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2answers
420 views

How to calculate formal charge?

I am trying to understand formal charge and how it is being calculated. I have copied the image from organic chemistry as a second language below: How do I calculate formal charge? In the book formal ...
-1
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0answers
22 views

What will be the product, a 6-membered ring or a 5-membered ring?

This is the question. Answer is given B. But according to me all options are wrong. My explanation; First there would be addition of Cl2 Now AlCl3 has 2 options about which Cl will it take. It will ...
2
votes
1answer
39 views

Friedel-Craft reaction with amide substituent

In this question, I know that aniline will not undergo FC reaction as it forms a complex with $\ce {AlCl3}$ and precipitates out. The answer given is (c) and I agree with it. However, the benzene ring ...
1
vote
0answers
16 views

Why does heating glucose in the excess of HI produce n-hexane? [duplicate]

Alcohols react with acid halides such as $\ce{HI}$ to create alkyl halides, as such: $$\ce{C2H5OH + HX → C2H5X}$$ However, this doesn't seem to be the case with glucose, as the entire chain is ...
0
votes
1answer
46 views

Does a C=C double bond donate electron or withdraw it?

I have learned that a $\ce{C=C}$ double bond is electron-rich because of the p-p overlap and hence can easily donate an electron pair: I agree with this statement. However, in a $\ce{C=C}$ double ...
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0answers
22 views

What is the product of the mono-iodination of the following? [on hold]

What is the product of the mono-iodination of 4'-hydroxyacetophenone? Attempt at solution:
9
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2answers
885 views

Complex organic molecules

I am studying astronomy and came across the following term in the astrochemistry course called 'complex organic molecules' or also written as COMs. My question is: What is exactly meant with these ...
-2
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0answers
12 views

Epoxide Formation for Anti-dihydroxylation [on hold]

Below I have posted my thought process for the epoxide formation in anti-dihydroxylation. I am very confused on the logic of this and would appreciate if anyone can help clarify this mechanism to me. ...
5
votes
2answers
1k views

Hydrogen bonding relating to molecular orbital theory

In [1, p. 232] here is an explanation of how alcohols hydrogen bond to each other and I do understand how the alcohols form hydrogen bonds to each other: FIGURE 6.15 Water and alcohols are ...
-1
votes
0answers
18 views

What should be the IUPAC name of the following Spiro compound?

According to me it should be named as: 9-Ethyl-6-formyl spiro[5.4] dec-3-ene-1-carboxamide Please check if I am correct.
6
votes
1answer
324 views

Mechanism for conversion of ketone to dichloride with phosphorus pentachloride

I would like to know the mechanism of this reaction leading to the formation of a geminal dichloride. I am unable to predict how the $\ce{C=O}$ breaks and how the 2 $\ce{Cl}$ atoms replace the oxygen ...
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0answers
29 views

What should be the IUPAC name of the following compound?

I think it should be named as 2-(cyclopent-1,4-diene)-2-methyl ethan-2-ol
15
votes
2answers
546 views

Etymology of alanine

Oxford dictionary online gives etymology of alanine as: Coined in German as Alanin, from aldehyde + -an (for ease of pronunciation) + -ine. But I see no resemblance to the aldehyde structure in ...
2
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0answers
20 views

Confusion about prioritizing functional groups in case of poly functional organic compounds

According to Wikipedia, sulfonic acid $(\ce{-SO3H})$ is comparatively stronger than carboxylic acid $(\ce{-COOH})$. Then why is sulfonic acid lower in priority than carboxylic acid (while naming poly ...
2
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6answers
3k views

Storage of Urine

Not all may be favorable to this project, but I will explain what I am trying to do. I work at home, and instead of walking a moderate distance to the bathroom and loosing my focus, I've been, at ...
1
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0answers
74 views

Major product for aldol condensation between acetophenone and acetaldehyde

Crossed aldol condensation is done between acetaldehyde and acetophenone by using NaOH as the base. So, here we can get 4 possible products. But which one would be the major? I know that acetaldehyde ...
0
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0answers
12 views

Acid medium versus Basic medium characteristics in organic reactions [on hold]

I am kind new in the study of organic reactions and I have collected some points to write differences between acid medium and basic medium: Acid medium 1)favors strong oxizidation 2)favors ...
-1
votes
0answers
18 views

Nucleophilic attack on carbonyl vs. SN2 - who wins?

If a nucleophile is to attack the above compound, how do I determine wheather it kick the chlorine atom out via an SN2, or will it attack the electron deficient carbonyl? Does it depend on the ...
3
votes
1answer
113 views

How does Grignard reagent form? [duplicate]

So I've read that during the formation of the Grignard reagent, The R-X bond cleaves homolytically forming free radicals. My question is how is this happeneing? Due to the high electronegativity ...
4
votes
0answers
77 views

Ene-yne metathesis product

In the ene-yne metathesis how to know which product will form predominately, as the mechanisms to both are plausible?
3
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0answers
69 views

N,N-Dimethyl-2-(indol-3-yl)glyoxylamide from indole

I would like to know how to obtain the following molecule, whose technical name should be something like N,N-dimethylindol-3-ylglyoxylamide (let's call it DMIG for short) One of the constraints being ...
3
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0answers
66 views

Why does my synthesized 4-bromoacetanilide smell like almonds?

So, I synthesized 4-bromoacetanilide in the lab by brominating acetanilide. Acetic acid was used as a catalyst. Sodium bisulfide was used to neutralize the reaction product. Then it was washed with ...
1
vote
0answers
209 views

What are the differences between silicone with phenyl and silicone with methyl groups?

I'm doing a work on silicone polymers and my question is what is the difference, in therms of consistency and viscosity, and the chemical differences (properties) between benzenic silicone and ...
13
votes
1answer
306 views

ICHO Synthesis Problem 2018

I've several doubts about this ICHO synthesis problem, which was a part of the preparatory problem package of 2018 (so yes, it's not a part of an ongoing contest) Before sharing the answer given, I'...
4
votes
1answer
179 views

Influence of neighboring fluorine and hydroxyl on carbocation

Which of the 2-fluorobutan-3-yl and butan-2-ol-3-yl carbocations will be more stable? I know that fluorine has a greater electron-withdrawing inductive effect, but what about the resonance effect of ...
2
votes
1answer
109 views

Ester as a side product in the synthesis of bromoalkane from alcohol. Is it correct?

About 5 months ago, I answered a very interesting question albeit a very simple one. Why do we need sulfuric acid in creating alkyl bromide and not in creating alkyl iodide from alcohol and ...
8
votes
1answer
55 views

Alcohol or Carbonyl - Which is more reactive towards PCl5?

We're aware that ketones and alcohols both react with phosphorus pentachloride, to produce geminal dichlorides and alkyl chlorides respectively. What happens in the compound shown below, when ...
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vote
0answers
42 views

Disiamylborane on alkyl halides

I am having problem predicting the last product in the following reaction: $$\ce{CH#CH ->[Na/NH3 (l)][(Excess)] (P) ->[DCl] (Q) ->[(i)Sia2BH][(ii)CH3COOH] (R)}$$ I am getting an alkyl ...
0
votes
1answer
43 views

heating methane in a vacuum chamber [on hold]

Using radio waves to heat, and electromagnetic fields to contain....could methane be heated to much higher temperatures than via simple oxygen/combustion, thus producing a much higher specific impulse ...
0
votes
0answers
19 views

What does [O] denote in organic redox reactions? [duplicate]

I've seen a few examples in the lectures we've been having and I wasn't able to find any sources talking about it. I think I remember a previous teacher saying it was a symbol for oxidation itself, ...
4
votes
1answer
261 views

Isocyanides undergo addition reactions, but cyanides do not. Why?

My book mentions addition reactions of isocyanides with halogens, ozone, sulphur, etc. but it doesn't mention any such reaction for cyanides. Instead, it bluntly states: "Cyanides do not undergo ...
0
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1answer
84 views
+50

Reaction of urea and thiourea with nitrous acid

I was told that urea on reaction with nitrous acid gives nitrogen gas, carbon dioxide and water. While on the other hand, thiourea on reaction with nitrous acid gives $\ce{H+}$, thiocyanate ion and ...
9
votes
1answer
7k views

What does the “s” mean in s-cis and s-trans conformations

I am learning about conjugated unsaturated systems, and came upon s-cis and s-trans conformations in conjugated dienes. So what does the "s" mean in s-cis and s-trans conformations?
-1
votes
1answer
28 views

Rate of reaction [on hold]

If I recall correctly I was told that the rate of reaction approximately doubled for every 10 degree C rise in temperature. Is the a similar rule of thumb for increase in pressure. I am working on ...
4
votes
2answers
68 views

Do alkyl halides with an alpha nitrogen atom undergo SN1 reaction?

Today, in my organic chemistry class, I learnt about the nucleophilic substitution reaction. The notes have stated that: Alkyl halides with $\alpha$ oxygen atom can also undergo SN1 reaction ...
0
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0answers
27 views

Nomenclature of 1-ethoxypropan-2-ol [on hold]

Consider the following compound: Why it is named 1-ethoxypropan-2-ol and not 2-ethoxypropan-1-ol?
5
votes
0answers
157 views

Reaction of cyclopropane with hot potassium permanganate

Hot potassium permanganate is usually used as an oxidising agent, and cyclopropane being an unstable three membered ring undergoes reaction with several reagents such as bromine, $\ce{HBr}$, metal ...
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votes
1answer
10 views

Analogy of hydrocarbon chain length properties [on hold]

What sort of analogy is good to use for remembering how the length of hydrocarbon chains affect the properties such as melting point and volatility?
12
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2answers
350 views

Can the amount of shielding in proton NMR caused by ring currents be predicted?

My textbook (Organic Chemistry, 2nd Ed. Hornback, Joseph) states that if a hydrogen is located near the center of an aromatic ring it will experience an (often quite sizable) upfield shift, as seen in ...
-1
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1answer
131 views

What is the final product of a carbohydrate treated successively with hydrogen cyanide, water, and hydrogen iodide/ phosphorus?

An unknown carbohydrate is successively treated with (1) hydrogen cyanide, (2) water, and (3) hydrogen iodide and phosphorus: $$\ce{C6H12O6 ->[HCN] X ->[H2O] Y ->[HI,P]Z}$$ What is the ...