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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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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 ...
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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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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 ...
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1answer
44 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 ...
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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 ...
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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 ...
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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 ...
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1answer
38 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 ...
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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:
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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. ...
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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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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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2answers
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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 ...
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0answers
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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.
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0answers
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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
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0answers
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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 ...
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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 ...
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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 ...
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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'...
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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, ...
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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?
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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 ...
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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?
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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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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 ...
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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 ...
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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?
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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 ...
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 ...
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0answers
18 views

What is the reaction mechanism for this synthesis of MCPO (bis[2-(methoxycarbonyl)phenyl] oxalate) + 2HCl from methyl salicylate and oxalyl chloride? [on hold]

Can somebody please kindly explain to me what triggers the reaction and how the reaction is done mechanistically and what drives the reaction until MCPO?
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0answers
20 views

Order of dipole moment [on hold]

Arrange o-chlorotoluene, m-chlorotoluene, p-chlorotoluene in increasing order of dipole moments. The answer is the same order as given but I don't get why.
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1answer
42 views

A wrong trivial name?

Isopropyl chloride should have been called secondary propyl chloride, right? The first iso must be isobutyl chloride, methinks.
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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 ...
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0answers
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Drawing bonds and delocalised electrons in condensed formulae

The $\LaTeX$ mhchem package provides commands for drawing bonds within condensed chemical formulae. Some of them have a clear allocation to covalent bonds while others have not. Single, double, and ...
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0answers
9 views

Reaction mechanism of elimination reaction [closed]

My question is about the reaction mechanism when 1-Bromoethene reacts with Sodamide .
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0answers
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Vitamin C for aquarium usage

i would like to dose Vitamin C on my reef tank, based on an article that i found online. Now, the dose consist on 2xday powder usage, diluted on water before using, and as always in aquarium, in high ...
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0answers
41 views

number of optical isomers of a cyclic molecule

What is the number of optical isomers for this compound? Also, there seems to be no clear-cut boundary between geometrical isomers and optical isomers. Referring to a post in StackExchange, is (RS)- ...
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0answers
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Determining chemical formula of the hydrocarbon via combustion analysis [closed]

A container of volume $\pu{15 L}$ contains a hydrocarbon at $\pu{27 °C}$ and $\pu{2 atm}$ pressure. For the analysis, we take $\pu{10 g}$ of hydrocarbon and the pressure becomes $\pu{1.718 atm}$ (at ...
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0answers
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What is the chemical equation of pyrolysis process? [closed]

To be specific, I want to know the chemical equation of pyrolysis of waste plastic which is polystyrene, forming syngas, char and pyrolysis oil.
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If the energy less than the work function is phton ejection of electron can occured? [closed]

If the energy less than the work function is phton ejection of
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0answers
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How to assign locants in 3-chloro-4-ethylhexane?

For the compound shown above, which name (3-chloro-4-ethylhexane or 4-chloro-3-ethylhexane) is correct? Do we need to first look for the minimum number set, and check alphabetical priority only if ...
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1answer
29 views

Question about Carboxylic Acid Nomenclature

According to my chemistry textbook, 2-hydroxy-1,2,3-propanetricarboxylic acid is represented as: But 5-bromoheptanoic acid is given as: In the former nomenclature, propane is taken as the base ...
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0answers
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Detecting alkaloids - Dragendorff's reagent

I am writing a book and as part of the plot one of the characters has a plant that contains alkaloids in tincture form. They want to do a test to detect for the alkaloids so they use the Dragendorff's ...
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1answer
22 views

Acid catalysed dehydration of unsymmetric alcohols

How to find the major product of acid catalysed dehydration of unsymmetric alcohols. For example, in the dehydration of butan-2-ol using conc. H2SO4, which is the major product? But-1-ene or But-2-ene?...
3
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1answer
35 views

Quaternary Ammonium salts and peroxy acid

I came across this question in my test: This compound is treated with $\ce{CH_3CH_2I}$ and then with $\ce{H_2SO_5}$ and heated. The product is: A) B) $\ce{CH_2CH_2}$ ...
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0answers
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I need help to explain the reaction of a dissolvable magnesium alloy to the masses (Reaction within) [closed]

We use a Magnesium based metal alloy in an application where when the alloy is exposed to water with a high salinity (Chlorides) it dissolves. The below chemical reaction was provided and we would ...
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0answers
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A 25.33g sample of BaO is found to contain 13.73g of barium. What is the percent by mass of the barium and oxygen in this compound? [closed]

**A 25.33g sample of BaO is found to contain 13.73g of barium. What is the percent by mass of the barium and oxygen in this ...
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0answers
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Number of products on dehydrobromination

Question: The total number of alkene products possible from the dehydrobromination of 3-bromo-3-cyclopentylhexane using alcohol KOH is : This question was asked here before but I am getting more ...
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1answer
47 views

Depicting molecules by Natta projection

Does anyone know the meaning of these two bonds in stereochemistry? These bonds are provided by the $\mathrm{\LaTeX}$ chemfig package. The creator of the ...
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0answers
33 views

Why is the methyl chloride and sodium hydroxide reaction irreversible?

Is the reaction of methyl chloride and sodium hydroxide (aq) irreversible simply due to the relative stability of sodium hydroxide and sodium chloride? Or is there more to it than that?