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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Oxidation of alcohols by Ceric Ammonium Nitrate

I have realized that reaction with ceric ammonium nitrate essentially results in coordination of alcohol with $\ce{Ce(IV)}$ and my teacher referred that we should be able to proceed it to form ketone ...
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Mechanism of reaction of alcohol with NaBr + H2SO4

My teacher told that the mechanism for reaction of alcohol with $\ce{NaBr + H2SO4}$ follows SN1 when alcohol is 2°/3° and SN2 when it is primary or methanol. He told that the reactivity of alcohol ...
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2answers
299 views

What is the name origin of ester?

Ester is quite a random nomenclature for a compound derived from a parent acid and parent alcohol. Is there any reasoning behind using the word 'ester' to name such compound (for memorising purpose)? ...
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1answer
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Why does there need to be a planar intermediate in 2,2'-dibromobiphenyl when one of the phenyl groups rotates?

I was in class and my professor brought up the example of 2,2'-dibromobiphenyl: In her example, one of the bromines was actually pointing into the page and the two phenyl groups were not actually on ...
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0answers
22 views

Free energy calculation [closed]

Calculate the reaction free energy of H2(g) + I2(g) 2HI(g) when the concentrations are 0.006 mol L-1 (H2), 0.03 mol L-1 (I2), and 1.27 mol L-1 (HI), and the temperature is 700K. For this reaction Kc ...
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Comparing stability of radicals

I was asked to compare the stabilities of the following radicals: Allyl radical, Methylcyclohexyl radical, 3-bromo-butyl radical, methyl radical and 2-methylphenyl radical This is the order I came up ...
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1answer
55 views

How does Al-Hg react with carbonyl in presence of concentrated HCl?

In Clemmensen reduction, $\ce{Zn-Hg}$/ $\ce{ conc. HCl}$ reduces the carbonyl $\ce{>C=O}$ to $\ce{>CH2}$, by the following mechanism(?): What happens to the carbonyl group if we replace Zinc ...
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1answer
37 views

Do we need to check for all kinds of symmetry in a compound to declare it achiral?

I know that a compound is achiral if it contains any one of the following kind of symmetry. 1.Plane of symmetry 2.Centre of symmetry 3.Normal axis of symmetry 4.Alternate axis of symmetry It is ...
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1answer
40 views

Fischer indole synthesis: significance of choice of acid catalyst

Lately, as a matter of interest, I have been studying sigmatropic rearrangements. I came across the Fischer indole synthesis, whose Wikipedia article states: The Fischer indole synthesis is a ...
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0answers
67 views

How to use NMR readings to determine the molecular structure of a compound? [closed]

A question in my exam came as follows: How is NMR used in the determination of structure of organic compounds? I have studied NMR spectroscopy and I know how to determine values using an NMR ...
3
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1answer
75 views

Strength of nucleophiles among SN1 and SN2 reactions [closed]

As per the theory of chemistry, we say that unstable carbocations undergo SN2 reactions as it involves strong nucleophile. As a consequence, it does not lead to the formation of reaction intermediate, ...
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0answers
26 views

Major product from allylic halogenation of alkenes

Allylic halogenation of butene happens in the following way: The RDS of this radical chain mechanism is allylic hydrogen abstraction ($\ce{H_a}$) from the allylic position to give a 1° allylic ...
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0answers
38 views

Priority of factors while deciding acidic strength / stability of conjugate base (oxyanions)

I am facing a lots of problem while deciding acidic strength. I am unable to figure out that which factor would be the deciding one or what is the priority order. My approach For comparing acidic ...
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0answers
29 views

Organic chemistry question [closed]

Can anyone pls solve the given question that :-> How many functional groups are present in the following molecule?
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26 views

Strange Distillation Behavior

I was attempting a fractional distillation with 1mL water and 1mL propylene glycol, and I’ve been encountering strange behavior with the heating of the mixture. The heating curve shows strange “spikes”...
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0answers
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Why do carboxylic acids have higher boiling points than equivalent alcohols? [closed]

Why do carboxylic acids have higher boiling points than their equivalent alcohols isomer?
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1answer
23 views

Any plastic for long term storage of Puriss. Ethanol?

I'm being offered to share some puriss Ethanol. Can I store it long term in any plastic container without the slightest contamination/reaction from the plastic? I have HDPE, PET, but I could buy ...
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0answers
36 views

Is glycine molecule a polar or nonpolar molecule? [duplicate]

Infos say that glycine is nonpolar as an amino acid but it is a POLAR molecule. what is more valid? What is the distinction between the two?
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1answer
57 views

Mechanism of reaction of benzenediazonium chloride with ethanol to form benzene and acetaldehyde

In my textbook, all that was told was that ethanol is a mild reducing agent and hence reduces BDC while oxidising itself. Is there any mechanism or am I just supposed to remember this like a redox ...
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3answers
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What does washing and drying a solution mean?

After combining two solutions, a direction in a 1970s British chemistry book says to wash the new solution with a mixture of baking soda, table salt, and water. Then it says to dry it with anhydrous ...
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3answers
259 views

Isomerization reaction involving carboxylic acid derivatives

I have tried searching for what type of organic reaction this is in my textbooks and ended up with nothing. Thus, I could not fully understand and refer to the mechanisms that the solution has ...
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1answer
48 views

Reduction of epoxide

Does $\ce{LiAlH4}$ and $\ce{NaBH4}$ reduce an isolated epoxide? I have two books where both are saying differently. One says it can and other says cannot. On searching the web there was no definite ...
2
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1answer
66 views

What does A. R. in A. R. sodium nitrite mean?

I'm reading about a reaction from a 1970s organic chemistry book. It references A. R. sodium nitrite. What does the A. R. mean? I see from online that "Ar" means aromatic ring. Is that the ...
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0answers
18 views

What do you call different formations of polycyclic molecules, such as the 'bent' phenanthrene vs. the 'linear' anthracene?

Are there terms, IUPAC or not, that describe multiple carbon rings fused in different shapes, like the aforementioned anthracene and phenanthrene? Also, I thought I read about a term describing carbon ...
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0answers
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Organic chemistry test question [closed]

This is a question from my test. I am not getting what to do in 1st step. 2nd step is clear to me.
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0answers
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What was the absolute and relative error in the weight? [closed]

The weight of Nissan Versa is 2, 354 pounds. Trying to theoretically calculate its stopping distance, one forgot to take into the account the weight of a 200 pound driver. What was the absolute error ...
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Will Polyurethane foam cause my lapel pins to corrode over a long period of time? [closed]

I have a collection of lapel pins (made in the late 80's to mid 90's) that I plan to preserve forever. My plan is to store my pins in a small 2"x 2" acrylic containers with a Polyurethane ...
3
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1answer
148 views

How to synthesize 4‐[(4,4‐dimethylpentyl)oxy]‐2,2,8,8‐tetramethylnonane starting with 4,4‐dimethylpent‐1‐ene?

My attempt: I don’t know how to add another chain. I think I probably need to react with another A molecule, but I don’t know the mechanism. Can anyone help me with this?
6
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1answer
216 views

Nomenclature of unusual nitrogen functional group

I am trying to create a proflavine derivative containing a 1,2,4-oxadiazole-5-one functional group, the first step produces an interesting functional group that I have no idea how to name: $$\ce{[Pro]-...
2
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0answers
66 views

Does 2‐indanone form a stable hydrate?

Following up the question Formation of a stable hydrate. I understand that for cyclopropanone the change in hybridization is the reason for stabilization of hydrate since it relieves the angle strain. ...
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0answers
37 views

What characterises the smell of alkane hydrocarbons?

I have heard that aromatic hydrocarbons smell fruity and like petrol. However, I understand that there is a class of hydrocarbons called alkane, as for example propane or butane. I wondered if I might ...
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0answers
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Comparing melting points of substituted benzaldehydes

The correct decreasing order of melting point for the given organic compounds is: 3 has maximum melting point because of intermolecular hydrogen bonding. I am unable to predict rest of the order ...
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0answers
26 views

Finding product when 3-ethyl-3-methylhexan-1-ol is dehydrated [closed]

Find the major product when 3-ethyl-3-methylhexan-1-ol is treated with concentrated sulphuric acid. I think it can be 3-ethyl-4-methyl-hex-3-ene. What should be the correct answer?
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59 views

Geometry of a free radical at the bridgehead carbon

With reference to J. Am. Chem. Soc. 1968, 90 (19), 5266–5267, they state: The most favorable geometry of aliphatic free radicals remains an unsolved problem, since existing data are consistent with a ...
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0answers
37 views

Is there a planar molecule that is optically active? [duplicate]

Can a planar molecule be optically active? As per my knowledge, any molecule which has a plane of symmetry cannot be optically active and planar molecules have a molecular plane of symmetry. So, can I ...
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1answer
93 views

Comparing stability of 2-propenyl cation and 1-propyl cation

Compare the stability of 2-propenyl cation and 1-propyl cation: $$\underset{\text{2-propenyl cation}}{\ce{CH2=CH-CH2+}}\qquad \underset{\text{1-propyl cation}}{\ce{CH3-CH2-CH2+}}$$ In 2-propenyl ...
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0answers
28 views

Why is the order of basic strength 4>2>1>3 [closed]

Please tell me reason for order of every structure
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0answers
45 views

Is 1,6-dimethylcyclohexene the name correct for this structure? [duplicate]

can anyone please help me saying that if this structure's name is 1,6-dimethylcyclohexane or not?
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0answers
17 views

Class of 1-bromo-2-butyne [closed]

What will be the class of 1-bromo-2-butyne? As this compound has two functional groups i can not understand in which class this compound will be classified? Alkynes are just hydrocarbons and hence ...
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0answers
33 views

Why is the carbon atom in methane primary? [closed]

I was taught about degrees about carbon atoms today. There was one thing that I did not understand though. If the degree of carbon atoms is defined by the number of carbon atoms it is bonded to, then ...
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1answer
78 views

Effect of isotopes on H-Bonding

The following question was asked in one of the assignments my teacher has given. Acetone ($\ce{Me2CO^16}$) on treatment with $\ce{H2O^18}$ gives a mixture of $\ce{Me2CO^16}$ and $\ce{Me2CO^18}$, the ...
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0answers
23 views

Nitration of 5-nitro-2-cresol [closed]

First of all , I'm confused about the charge density in the rest 3 positions , viz; 3,4 and 6 of the benzene ring .EAS is supposed to occur in the most electron rich position .But due to steric factor ...
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1answer
35 views

Hybridized/unhybridized orbital confusion and aufbau principal

When an atom becomes $\mathrm {sp}^2$ hybridized, the three hybrid orbitals that are created are lower in energy than the ones unhybridized. In an $\mathrm{sp}^2$ atom, say carbon, there are 4 valence ...
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1answer
54 views

Modifying a TLC mobile phase in order to increase the RF values

You are running a TLC using 50% ethyl acetate in hexane and find the resulting $R_f$ values are too low. How would you modify the TLC mobile phase in order to increase the $R_f$ values? Would the ...
3
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1answer
56 views

But what are anti-bonding pi-orbital? In search for an intuitive explanation

Imagine that you want to explain to an undergraduate why they have to to shade the pi-orbitals in a symmetrical way, i.e. dark on top (+), white on bottom (-) for two neighbouring pi-orbitals because ...
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17 views

Equilibrium calculations- ICE table [closed]

Question 1. Equilibrium calculations - ICE table. At a certain temperature, a 750 flask is filled with 0.250 mol of H 2 and 0.750 mol of HBr. The following reaction is observed: H 2 (g)+Br 2 (g) ...
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3answers
156 views

What do (2S,3S) and similar notations mean?

When my textbook is discussing stereoisomers with more than one chiral centers, it's using notation like (2S,3S) being an enantiomer with (2R,3R) and so forth. I understand R and S configuration, and ...
2
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0answers
35 views

Comparing stability of different compounds with a C=O group [closed]

Rank the following carbonyl compounds in order of stability ($1$ = most stable) My answer would be: (d)>(c)>(a)>(b) I’m just a bit confused since the most stable molecule in my choice has a ...
2
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2answers
142 views

Étard Reaction of Ethylbenzene

What is the major product when the following compound undergoes Étard reaction? Is it acetophenone or a terminal aldehyde. The mechanism discussed in Mechanism for an Étard reaction (chromium complex)...
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1answer
76 views

What does simplest optically active alkene mean? [closed]

I am confused between whether we will call 2,3-dimethyl-cyclopropene or 3-methylpent-1-ene as simplest optically active alkene. Does “simplest” mean aliphatic, or does it mean having least number of ...

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