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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.

2
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0answers
29 views

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 ...
0
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1answer
23 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
36 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) $\ce{CH_2CH_2}$ ...
-1
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0answers
16 views

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 ...
1
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0answers
38 views

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 ...
2
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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 ...
0
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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?
0
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1answer
26 views

Expanded structure formula and Lewis dot structure, whats the difference?

I am teaching my self the basics of chemistry and I have done lewis dot structure before. Right now I am going into carbon chemistry which often use structure formulas to represent compounds. There is ...
1
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1answer
53 views

Hydrolysis under basic medium

The first compound is said to be hydrolyzed more easily than the 2nd compound below under Alkaline medium . How is this possible ? I thought due to resonance, -NO2 acquires negative charge which ...
9
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0answers
53 views

Explanation of the strength of phosphorus-oxygen bond

When discussing the Wittig reaction, Clayden's Organic Chemistry cites the strength of the $\ce{P=O}$ formed in triphenylphosphine oxide as a driver of the reaction through enthalpy: The $\ce{P=O}$ ...
1
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1answer
49 views

Hydrogenation of 1-hexene with Raney nickel

For my high school senior chemistry project, I need to create and perform a lab. I've chosen to do the hydrogenation of 1-hexene with the catalyst of Raney nickel. I'm struggling because I'm not ...
0
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2answers
106 views

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 ...
1
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0answers
23 views

Basicity of nitrogen in amide versus basicity of nitrogen in aniline

I was wondering that how can we compare the basicity of nitrogen in amide to the nitrogen in aniline as in both structures the lone pair on nitrogen is in conjugation as shown below, Can someone help ...
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0answers
22 views

3-Hydrocypentan-2-one vs 4-Hydroxypentane-2-one, which one will (acid catalysed)dehydrate faster/to more extent

According to my understanding, the rds in acid catalysed dehydration is the removal of the hydroxy group. If that’s the case, shouldn’t ‘3’ have a more stable intermediate (i know resonance of ...
-1
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1answer
32 views

Why does charge separation decrease stability of resonances forms?

Why is an resonance form with negative and positive formal charges in its atoms, lets say +1 and -1, less stable than an resonance form with just positive or negative formal charges, lets say just +1 ...
0
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1answer
45 views

A doubt on the action of NBS/CCl4

Suppose we have a alkene( ex- 2- butene) we try to subject it to allylic bromination using NBS/CCl4 and then the mixture is separated using fractional distillation. According to me as the reaction ...
0
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1answer
72 views

Can anyone tell me what reaction is this?

I came across this reaction, but I have no idea what reaction is this. Can anyone please tell me? What will be the products? My first guess is that a carbene will be formed which will attack on the ...
-1
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1answer
30 views

Why is this named 3-phenyl-2-butanol instead of 2-phenyl-3-butanol? [closed]

Why is the following compound named 3-phenyl-2-butanol and not 2-phenyl-3-butanol? Does the alcohol or the phenyl group have priority?
0
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0answers
20 views

Combinatorics of Molecule given the Elements

I have search a lot on Internet and my own researches on a sheet of paper failed to found an analytical closed formula for the following problem: Considering: Common ranges of temperature and ...
1
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1answer
29 views

How can the stereochemistry of the product of an E1cb reaction be determined?

Say if this is your reagent. I guess similarly to how you'd determine the stereochemistry of the product of an E1?
1
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0answers
29 views

Nucleophile vs base and Electrophile vs acid [closed]

How we will figure out that a given compound will behave as nucleophile or base ? Same problem for electrophile and acid. By the way I have already seen a similar question though I didn't find it ...
1
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0answers
21 views

How many natural products are there in existence? [closed]

Hi I'm doing a project on natural products and I'm wondering if somewhere there is at least an estimated number of how many exist? If this exists somewhere can you please provide a reference. ...
0
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1answer
29 views

What is thermal isomerization?

Context: a retinal molecule the isomerizes from all-trans to 13-cis form, then "reisomerizes thermally". I tried googling it but couldn't find a simple, straightforward explanation.
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0answers
15 views

Are AcO- and PhO- better described as soft or hard nucleophiles?

I would presume soft nucleophiles as resonance increases the energy of the HOMO and therefore they favour SN2 over E2?
0
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1answer
105 views

What do the dots mean in HN.CO.CH3 connected to the second carbon of N- Acetylglucosamine? And what do the N and acetyl indicate?

What do the dots mean in HN.CO.CH3 connected to the second carbon of N- Acetylglucosamine? And what do the N and acetyl indicate?
0
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1answer
32 views

A mixture of 4 compounds is extracted with HCl. Which one would go to the aqueous layer? [closed]

So this has to do something with the H+ ion bonding with the compound. I dont know how to approach it. The answer given is 2
2
votes
1answer
70 views

Is an alcohol-based spray cleaner ok for cleaning an aluminum heat exchanger?

Simple alcohols such as ethanol can, apparently, corrode aluminum. However, this corrosion reaction seems to be very slow at room temperature and below. Is an ethanol based, non-foaming spray cleaner, ...
0
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0answers
29 views

What is the product when 1,4,6-trifluoroazulene is treated with sodium methoxide?

My logic During substitution via Path 1 and Path 2 aromatic intermediates are formed. Via path 3 anti aromatic intermediate is formed. Therefore reaction takes place via path 1 and path 2 only. ...
1
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1answer
13 views

EtG formation outside the liver

Ethyl glucuronide (EtG) is formed by conjugation with glucuronic acid catalyzed by the enzyme UDP-glucuronosyltransferase. My question: Is it possible for EtG to form spontaneously in a urine sample ...
0
votes
1answer
58 views

Total number of stereoisomers of 1,2-dimethyl-4-(propan-2-ylidene)cyclopentane [duplicate]

I don't think there is any change of showing geometrical isomerism across the double bond because the two groups on the right side (two $\ce{-CH_3}$) are the same. Also I don't think there should be ...
3
votes
1answer
82 views

How many stereoisomers are possible for 1,2-dimethyl-4-(propan-2-ylidene)cyclopentane?

How many stereoisomers (not counting different conformers) does 1,2-dimethyl-4-(propan-2-ylidene)cyclopentane have? I think the answer should be 3. There are two geometrical isomers (cis and ...
-1
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0answers
39 views

Can vicinal di-iodide get eliminated by itself?

When $\ce{CH2I-CH=CH2}$ (2-iodoprop-1-ene) reacts with $\ce{HI}$ in aqueous solution, by Markovnikov addition, $\ce{CH2I-CHI-CH3}$ (1,2-diiodopropane) is formed. In the answer by aventurin here?, it ...
-1
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0answers
13 views

Planarity of this molecule [duplicate]

Apparently CH2=C=CH2 is non planar as given in my school textbook However aren't the terminal C atoms sp2 hybridised and middle atom sp hybridised? In that case , how is it possible for this ...
0
votes
1answer
32 views

What is the displayed formula for methylpropene? [closed]

I am currently studying organic chemistry at school and I came across a question in my textbook which asked me to find the full displayed formula of methylpropene. I knew that there would be three ...
4
votes
0answers
48 views

Mechanisms of Birch and Bouveault-Blanc Reductions

The question is all about the sequence of a possible Birch- and Bouvault-Blanc-Reduction in this exemplary substrate. With which reduction the mechanism begin? My first attempt was to classify the ...
-1
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0answers
19 views

TD-DFT analysis using Gaussian

For the Pentacene molecule, there is an absorption chance in the range of 400nm-650nm that I can’t view by using TD-DFT analysis [![using Gaussian][1]][1] software. I tried different number of states ...
0
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2answers
66 views

what is the cross aldol product of ethanal and acetone(major product)?

my teacher told that major product would be when acetone will form nucleophile because it will attack more positive carbon of ethanal(less +i than acetone) however i read in my book that since ...
12
votes
2answers
390 views

Does aniline react with diazonium ions at C or N?

In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major ...
2
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0answers
29 views

Why does gilman reagent react with acyl chlorides but not with other carbonyls?

According to HSAB (hard-soft acid-base) concept, a soft nucleophile preferentially reacts with soft electrophile and a hard nucleophile with a hard electrophile. Since $\ce {R2CuLi}$ is a soft ...
0
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1answer
19 views

Nucleophilicity in Polar Aprotic Solvent [duplicate]

Why is it that fluoride is more nucleophilic than iodide in an aprotic solvent? The Clayden textbook suggests that lower-row elements of the periodic table are more nucleophilic since their valence ...
1
vote
1answer
45 views

Does an acetal need to have one hydrogen attached to its carbon?

I was asked to identify the functional groups in this molecule above. So far I have found an amide ($\ce{-NHAc}$), an ether ($\ce{-OBn}$), and a conjugated diene, but I was also told that there is ...
2
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1answer
39 views

Does the priority go for the longer substituent, the closer one, or one which contains a pi-bond in naming Alkenes and Alkynes?

In the new IUPAC nomenclature, the longest chain is given the priority over that which contains the most number of double bonds. In naming this alkene: From which end would we start numbering? ...
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1answer
34 views

6-oxoheptanal reaction with LiAlH4 [closed]

Is it possible? the reaction below
2
votes
1answer
31 views

RO- as leaving group in saponification process

If RO- is a stronger base than OH- (and leaving groups are weak bases), why is RO- a leaving group here?
2
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1answer
42 views

Hyperconjugation and the stability of alkenes

Clearly, this issue has been touched on here and here. However, I would like to raise a new point on the issue. I have always thought that stabilisation of the $\ce {C=C}$ $\pi$ bond via ...
-1
votes
1answer
48 views

Why can't you form an anhydride from an ester via nucleophilic attack?

The reaction referred to is the nucleophilic acyl substitution reaction, where the nucleophile is a carboxylate ion and the electrophile is the ester. I am having a difficult time visualizing why this ...
2
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2answers
40 views

Cis Orientation of dienophiles orientation of groups maintained in Diels Alder

When I was reading about Diels-Alder reactions, I was confused about the cis and trans rules for dienophiles, as shown below. The text told me that "a cis dienophile will generate a ring with cis ...
2
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0answers
22 views

Charge distributions in the transition state of the SN2 reaction

I understand that a similar question has been posed here. However, the scope of my question is framed differently. I will present analysis of two different sources of information and I would like to ...
0
votes
1answer
43 views

Does OH- attack carbonyl carbon in aldehyde during aldol reaction?

Why does $\ce {OH^-}$ not attack the carbonyl carbon in an aldehyde during the aldol reaction and instead, deprotonate the $\alpha$ hydrogen to form an enolate intermediate? Also, why does the ...
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0answers
28 views

Diels Alder stereoselectivity

I'm familiar with the endo rule as well as the regioselectivity of the reaction. However, what I fail to understand is the stereoselectivity of the product in relation to the diene. For example, in ...