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.
8,901
questions
2
votes
2answers
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Finding major product after dehydration
here,should I prefer hydride shift or a product with more $\alpha$ hydrogens?
my doubt is...as hydride shift is easier than methyl shift,the answer should be $a$ or $c$.if methyl shift takes place the ...
0
votes
1answer
30 views
Synthesis of 1-naphthaleneacetic acid: Methods
I am trying to synthesizing 1-naphthaleneacetic acid from naphthalene and monochloroacetic acid. I found some patents and papers, and I have tried to synthesis but the yield is low. I used iron powder ...
-2
votes
0answers
19 views
Why is F a bad leaving group? [closed]
Why is F a bad leaving group?
I thought that a good leaving group is one that tends to leave easily (=strong acid or weak base) and is stable (ergo a weak base or a strong acid).
So wouldn't F be a ...
-1
votes
0answers
14 views
Mechanistic detail for Dehydration of benzaldoxime with acetic anhydride reaction [closed]
Please draw out and explain the mechanism for Dehydration of benzaldoxime with acetic anhydride rection. I'm struggling to find anything about it. Thank youuu :)
-1
votes
0answers
33 views
Comparing rate of dehydration [closed]
First I made the products and tautomerised them
As the conditions for dehydration are not mentioned so I assumed acidic conditions. This means that all the compounds would follow $E^1$ mechanism.
This ...
8
votes
1answer
375 views
(E)-2-bromo-1,4-difluoro-3-iodobut-2-ene or (E)-3-bromo-1,4-difluoro-2-iodobut-2-ene
I am struggling with naming this structure either (E)-2-bromo-1,4-difluoro-3-iodobut-2-ene or (E)-3-bromo-1,4-difluoro-2-iodobut-2-ene.
I am aiming at the question whether there is also a ...
-1
votes
0answers
46 views
How can I weigh the compound that melts at room temperature?
I am conducting an organic synthesis experiment involving 2,3,5-tribromothiophene.
The melting point of 2,3,5-tribromothiophene is about 25-28 ℃, so it melts easily during weighing.
Whenever I weigh ...
-3
votes
0answers
14 views
Why (abundance of M+1)/(abundance of M)=(number of carbon atoms)*(1.1/100)?. Why simple unitary method and arithmetic doesnt work? derive the formula [closed]
what is the proof of the formula and how the formula works? why combinatorics and distributions have been involved in the calculation? why cannot we find the number of carbon atoms just by using ...
-2
votes
1answer
59 views
Is bromo(iodo)fluoro(chloro)methane possible?
So this compound is supposed to have all of the stable halogens a part of this molecule ,fluorine,chlorine ,bromine and iodine. Is it really possible?
Link :http://wiki/...
-3
votes
1answer
41 views
Stability of hydroxy aldehydes [closed]
I cannot understand if carbonyl adjacent to alkene stabilises or destabilises it. Generally, we say that more substituted alkene is stable. In those cases attached groups increase electron density of ...
3
votes
2answers
79 views
Mechanisms for Reimer-Tiemann and Kolbe-Schmidt reaction on deuterium labelled phenol
I was solving a bunch of reactions when I encountered the following:
So for the first question:
This is a Reimer-Tiemann reaction. I felt that the tautomerism would result in the deuterium getting ...
1
vote
1answer
54 views
Determining the most stable enolic form of 1-phenylbutan-1,3-dione?
Question
Which form of 1-phenylbutan-1,3-dione is more stable?
Answer
3-Hydroxy-1-phenylbut-2-enone
My question
I've been told that between the above two, 3-hydroxy-1-phenylbut-2-enone is more ...
1
vote
1answer
52 views
Carbocation stability + determining position of attack on a carbocation in SN1 reaction
It's implied that the right structure is the more stable carbocation because it undergoes the second half of an SN1 reaction, but I'm not entirely sure why:
I'm also not sure why the $\ce{MeOH}$ ...
-1
votes
1answer
27 views
How does the concentration of a liquid increase? [closed]
Here the answer is A, I thought that both solids and liquids had constant concentrations and only aqueous solutions and gasses have changes in concentration. how does adding extra ester increase the ...
0
votes
0answers
50 views
Comparing the degree of dehydration
I am confused regarding the following problem which asks to arrange the given compounds in decreasing order of their degree of dehydration
My attempt at the solution:
I tried to find out the ...
4
votes
1answer
163 views
Assigning E–Z configuration for alkenes with cyclic substituent groups [duplicate]
I was taught that according to CIP rules, we must check the priority order for the substituents. But how can we do the same for molecules with cyclic groups as substituents?
How do we compare the ...
-1
votes
0answers
14 views
Identification of functional group [closed]
my own solution
A
R + NH3 + → NH4NO3
R = HNO3
HNO3 = liquid
NH4NO3 = solid
Accelerates the burning of combustible material. Produces toxic oxides of nitrogen ...
9
votes
4answers
269 views
What is an example of chemical reaction that can be assisted by both an inorganic catalyst and an enzyme?
I have been researching chemical reactions of inorganic catalysts and enzymes and cannot find a chemical process where an inorganic compound can be replaced by an enzyme (or vice versa) and have the ...
2
votes
1answer
165 views
How can a compound having a plane of symmetry be Chiral?
The compound( Given in the image below) is treated with $\ce{excess H2 in Pt}$.
Here, (a) - The given compound. (b) - What the answer should be according to me.
(c) - What the actual answer is:
Q1 - ...
-3
votes
0answers
27 views
Stability of organic carbocations. Aliphatic vs aromatic hydrocarbons [closed]
What is relatively more favourable, the formation of carbocations in aliphatic hydrocarbons or in aromatic ones?
How aromaticity dictates (if it does) the answer to the above question?
2
votes
1answer
54 views
Why is Maleic Acid more soluble in water than its trans isomer Fumaric Acid?
My teacher taught me that compounds having intramolecular H-Bonding are relatively less soluble in water as they will not involve in H-Bonding with water appreciably while those able to do ...
2
votes
0answers
81 views
+50
How stable is Remdesivir when vial vacuum is broken and/or it is reconstituted with sterile water?
I was recently looking at how long can Remdesivir be stored in its different forms.
I came up across several articles provided by the FDA and Gilead Sciences and others.
What caught my eye was the ...
-2
votes
2answers
22 views
Determination of the molarity of the diluted vinegar [closed]
Procedure of determination of acetic acid in vinegar
10 ml of vinegar is diluted with distilled water to the mark in a 100 ml of volumetric flask.
Then, 20 ml of this diluted vinegar is pipetted into ...
1
vote
2answers
43 views
Intramolecular Cannizzaro reaction product
I came across the following question :
My reasoning was as follows :
It can't be option (c) because there is no chance of losing a carbon during Cannizzaro's reaction
It can't be option (b) because ...
0
votes
0answers
26 views
Alcohols are a homologous series. However, you can get aromatic, aliphatic and alicyclic alcohols. Are there separate homologous series for each type? [closed]
In my textbook, it says that alcohols are one homologous series with the hydroxyl (-OH) functional group. However, there are aromatic, aliphatic and alicyclic alcohols. In one homologous series, can ...
2
votes
0answers
43 views
Can't aluminium chloride do electrophilic substitution as an electrophile?
In halogenation reaction of benzene, $\ce{AlCl3}$ is used as a catalyst in order to form electrophile $\ce{E^+}$.
So I was wondering that $\ce{AlCl3}$ is a Lewis acid (that fact being also used in ...
-1
votes
0answers
46 views
Chlorination of (1S)-1-phenylethan-1-ol to (1S)-2-chloro-1-phenylethan-1-ol
I am wondering if it is possible to chlorinate/brominate (1S)-1-phenylethan-1-ol on the second carbon of the ethanol. Though unconventional given that it is usually made by the enantioselective ...
1
vote
2answers
149 views
NMR spectrum chemical shift confusion
Recently started on NMR spectrum, and I'm slightly confused about chemical shifts and their connection to the resonance frequency and magnetic field.
From what I know, the "new" way of doing ...
0
votes
1answer
45 views
Phase of reaction between glucose and potassium cyanide to form amygdalin
I'm trying to write a detective-fiction novel, and I was wondering if potassium cyanide reacts with sugar only if the glucose for the amygdalin to form is dissolved in liquid or does it react even if ...
0
votes
0answers
23 views
Confusion regarding reaction pathway followed in reaction with lucas reagent
Recently I came across a problem involving Lucas reagent. It asks what is the major product when 2-methylbutanol is treated by HCl in presence of anhydrous ZnCl2? The answer says major product is 2-...
-1
votes
0answers
16 views
How to switch concentration of 30/70 water/ethanol through dialysis? [closed]
I mistakenly dialysed a preparation in ethanol such that it is now 30% water and 70% ethanol. How do i make switch the water/ethanol concentrations (70% water and 30% ethanol) via dialysis again? The ...
4
votes
0answers
33 views
Mechanism for removal of trimethylsilyl directly bonded to carbons
I recently came across a scheme for the synthesis of panacene (Sabot et al., 2008OrgLett4629):
In this synthesis, the step from 14 to 9 in removes a trimethylsilyl ($\ce{TMS}$) group directly bonded ...
4
votes
0answers
33 views
Reactivity order of DIBAL-H and diborane with esters and acids
I have been taught in class that
DIBAL-H is more reactive towards esters than carboxylic acids while opposite is true for diborane.
Also DIBAL-H mentioned is taken under low temperatures (−78 °C).
I ...
4
votes
0answers
80 views
+50
How does the reaction of Alkyl Halides with sodium nitrite in DMF proceed?
I was aware of the reaction of alkyl halides with Aqueos Sodium Nitrite which results in the formation of an alkyl nitrite but I came across the following reaction and was confused of how that would ...
3
votes
1answer
31 views
Which has higher priority between unsaturated ring and unsaturated chain in the nomenclature of organic compounds?
According to the IUPAC rules of nomenclature, alkenes have higher priority over rings but what if the ring also contains a double or a triple bond?
For eg:
Is this compound going to be named as 1-(2-...
-2
votes
0answers
13 views
About the reaction of Nafamostat [closed]
In this case, doesn't it imine react? I think that only ester part is hydrated though..
1
vote
1answer
53 views
Properties of stilbene isomers
(E)-stilbene may be separated by crystallization from (Z)-stilbene and the side product of the Wittig reaction, triphenylphospine oxide (TPPO), by using absolute ethanol. My question is why? (E)-...
5
votes
0answers
145 views
Can cis-trans isomers have same InChI?
From all we know only tautomers should get the same InChI key, or, in case of the second block, if there are lots of stereo centers. However these cases are just collisions, they still have different ...
-2
votes
1answer
18 views
silyl ketene acetal vs Benzene, which compound has a higher nucleophilicity? [closed]
With the use of Lewis acid Aluminium Trichloride, which one would have a stronger nucleophilicity? Silyl Ketene Acetal (CAS: 31469-15-5) or a phenyl group?
0
votes
0answers
25 views
Bond lengths in Fullerenes [duplicate]
I came across this about fullerenes-
All carbon atoms are equal and the undergo sp2 hybridisation. Each carbon atom forms three sigma bonds with three other carbon atoms. The remaining electron at ...
0
votes
1answer
27 views
Positional isomers [closed]
How many positional isomers are possible for the following molecule?
(a) 6
(b) 7
(c) 5
(d) 4
To know how many positional isomers for molecule, should I change the position of the functional group ...
-2
votes
0answers
22 views
Why we mostly consider benzene in terms of aromatic compounds? [closed]
In my elementary school books we always considered benzene as an aromatic compound and performed all reactions through benzene but never any other aromatic compound?
-1
votes
0answers
22 views
Why does my lab assignment use hexanes (a mixture of isomeric six-carbon alkanes) to isolate limonene from an orange peel?
My lab assignment has us use hexanes (a mixture of isomeric six-carbon alkanes) to extract limonene (a terpene) from the essential oil from an orange peel. I can't find information on whether limonene ...
5
votes
1answer
99 views
Comparing acidic strengths between benzylammonium ion and phenol
Question
Compare the acidic stengths between benzylammonium ion and phenol.
I first tried to remove the H+ ion from both of them and tried to compare the relative stabilities of resulting conjugate ...
-4
votes
0answers
27 views
Is there any situation wherein we can break the partial double bond of carbon and a halogen in an aryl halide arriving at 2 separate products? [closed]
Haloakenes and haloarenes related. Including the concept of resonance.
4
votes
0answers
42 views
Why 9BBN's rings don't migrate during hydroboration-oxidation?
My organic chemistry textbook (Clayden, Warren, Greeves) says this:
If we use the $\ce{HBR2}$ reagent $\ce{9-BBN}$, then only the
non-cyclic substituent formed in the hydroboration reaction will
...
4
votes
0answers
41 views
What functional group is this in this specific molecule?
I know without the nitrogen this molecule would probably be considered a crown ether. What exactly would the nitrogen/oxygen functional groups be named as in this molecule shown below? Any help would ...
-3
votes
0answers
27 views
What is the HOMO of a molecule with 8 conjugated electrons? [closed]
I know this is a basic question. Can I just assume that this will work: solve for n in Huckel's Rule (4n+2), so n=1 in a molecule with six pi electrons? And then LUMO is (HOMO + 1)?
*Edited to change ...
2
votes
1answer
35 views
What is the difference between an Aryl Halide and a Vinyl Halide?
Are aryl halides a type of vinyl halide? From my knowledge, when a Halogen atom is directly bonded to a doubly bonded carbon atom it is a Vinyl halide. When we look at halogen atom directly bonded to ...
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votes
0answers
27 views
chemistry 2 final about organic chemistry asap pls [closed]
I need this as soon as possible please. Any help would be appreciated
