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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15 views

Is shampoo or soap a better emulsifier?

Made homemade shampoo using: Sodium lauryl sulfate (SLS) Glycerin 95% ethanol Sodium stearate Made homemade soap using: 20% sodium hydroxide Vegetable oil 95% ethanol 20% sodium chloride After doing ...
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Olivetolic acid synthesis

I have both Malonyl - CoA and Hexanoic Acid at my disposal. There is very little information on the SYNTHETIC process of olivetol acid. From my understanding, you must first convert the two CoA's into ...
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Do we need to consider hydrogen bonding in organic molecules before deprotonation for comparison of acidic strenghts?

Let's suppose in this question hydrogen bonding would be considered in structure 3 ... if yes, then it would be a weak acid because it will not donate H+, but according to the answer given in the book ...
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Retrosynthesis of {6-[2-(benzylamino)ethyl]-1,4-dihydropyrimidin-4-yl}methanol

I have {6-[2-(benzylamino)ethyl]-1,4-dihydropyrimidin-4-yl}methanol (at the top) and have to make the retrosynthesis steps for my class. I tried different things but I'm not sure about it. In 1 you ...
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1answer
35 views

Reactivity of Alkenes with HBr

I am new in the Organic Chemistry (World of Reactions). I had got one question in my test. But, when I had seen it, I got no proper logic to tick the correct answer, and then when I saw solution, then ...
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If most drugs are made from hydrogen, nitrogen, oxygen, and carbon, then why can't I make drugs out of the air? [closed]

If most drugs are made from hydrogen, nitrogen, oxygen, and carbon, then why can't I make drugs out of the air? Is there a name for using photons to excite the atomic structure of gas to change its ...
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1answer
27 views

How to dissolve and homogenize DNA

I have about 20-30 grams of purified mammalian DNA preserved in EDTA. It is clumped up and solid. I need to dissolve and homogenize it, so it can be aliquoted, without damaging or lysing or ...
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Why grinds the pigments (from rose petals) up with solid in order to indentify the pigments? [closed]

Rose petals contain a variety od different pigments. Student wanted to identidy them. She grinds the pigments up with a solvent. Explain why
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Why isn't the aniline hydrolysed in Sanger's protein sequencing method?

Recently I was reading about identifying N-terminal amino acid residues using Sanger's reagent (1-fluoro-2,4-dinitrobenzene). The following image showing the reaction is taken fro Wikimedia Commons: ...
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What is the meaning of a “halide component” for Friedel–Crafts reaction?

Among the given halides, which one can be used as halide component for Friedel–Crafts reaction? (a) Isopropyl chloride (b) Bromobenzene (c) Chlorobenzene (d) Chloroethene I don't understand what a &...
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Inductive Effect of -CH3 group [duplicate]

3° carbocations are the most stable because of the +I effect of -CH3 group. This group gives a slight negative charge to the central carbon atom, which makes it less positively charged and thus, more ...
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ortho-bromoanisole + NaNH2 + Liquid NH3 =?

when we add ortho-bromoanisole in NaNH2 + NH3 we form products using the benzyne mechanism. here, we form the products considering only -I effect of -OCH3, if we consider its +M effect we would form, ...
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The effects of pH on the hydrolysis of Aspirin [closed]

I am doing an experiment in which I have different pHs of HCl (1.5, 2, 2.5, 3, 3.5), and I am seeing how leaving aspirin in a more acidic solution will cause it to hydrolyze into more salicylic acid ...
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Regarding the mechanism of oxymercuration-demercuration of alkenes

I'm trying to write the reaction mechanism of oxymercuration-demercuration of alkenes. The one my textbook gave is this : Alkene react with mercuric acetate in a mixture of water and THF to produce ...
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During denaturation of protien why does the 1degree structure remain intact while 2degree and 3 degree structures are destroyed? [closed]

I court the words written in NCERT cbse: "During denaturation 2 degree and 3 degree structures are destroyed but 1 degree structure remains intact. The coagulation of egg white on boiling is a ...
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How does deprotonation works?

I've been studying organic chemistry and came across this example : CH3-CH2-CH(+)-CH3 ---> CH3-CH=CH-CH3, the explanation the textbook gave was related to deprotonation. I've tried drawing lewis ...
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Regioselectivity of hydroboration-oxidation of enol ethers

In the book Hydroboration and Organic Synthesis, on p. 99, it is written that: hydroboration [of enol ethers] proceeds regioselectively, placing essentially all of the boron atoms at the β position ...
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Comparing acidity between 4-hydroxybenzaldehyde and 2-hydroxybenzaldehyde

https://hmdb.ca/metabolites/HMDB0011718 https://hmdb.ca/metabolites/HMDB0034170 The above two links provide the pKa values for the 4-hydroxybenzaldehyde (pKa = 7.32) and 2-hydroxybenzaldehyde (pKa = 8....
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Can you react dilute nitric acid and sucrose? [closed]

I've only seen information online that concentrated nitric acid can react with sucrose, but can a nitric acid solution with a molarity ranging from 3M to 5M also react with sucrose to create oxalic ...
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1answer
43 views

Continuous variable for graph of boiling point of different chain lengths

Looking at the boiling points of alkanes (for examples), many graphs plot boiling point against chain length : However, there is an issue with the line of best fit- since chain length is a discrete ...
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Confusion regarding rate determining step [closed]

What is the Rate Determining Step in an aldol reaction? I surfed through a lot of sources, but it isn't mentioned exactly about the RDS; What I found was this mechanism almost everywhere: In the ...
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What is the structure of this molecule given its NMR and IR data? [closed]

The formula of the molecule is C7H6O3. According to its IR spectrum, it is a carboxylic acid. Its C NMR spectrum consists of 5 peaks, so there are 5 different carbons. Its H NMR spectrum consists of 4 ...
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Why aldehyde group is easy to oxidize than hydroxyl groups of glucose

In all the reactions i had Seen I pointed out that aldehyde groups of a compound like glucose are easy to oxidize than the hydroxyl groups. I had also read some similar answers but I was unable to ...
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If on one amino acid, there are two amine groups and two COOH attached, and all of their 4 pka values are given how do you find the isoelectric point? [closed]

If on one amino acid, there are two amine groups and two COOH attached, and all of their 4 pka values are given how do you find the isoelectric point?
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Can methyl carbamate protected acid chlorides undergo friedel craft acylation [closed]

My question is can this acid chloride undergo friedel crafts acylation or is the carbamate group labile under those conditions or can any other problems be suggested that might inhibit that reaction. ...
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Hydrolysis in the presence of a base [closed]

I have read that hydrolysis can be either an SN1 reaction or an SN2 reaction. However, in the presence of a base, it is more likely to undergo SN2 than SN1. Is this true? For example, if I have three ...
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1answer
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Why this structure is diastereomers instead of enantiomers

In this diagram optical isomers has divided in to 2 categories, one is diastereomers and enantiomers. Is the example for diastereomers correct? For me its looks like enantiomers
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Intermediate vs final product stability [closed]

What's more important in a reaction mechanism, the stability of intermediate or stability of final product formed? For example, look at the attached image. Here if we look for more stable intermediate,...
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1answer
48 views

Limescale passivation by citric acid?

Cleaning products producers advise against using "home remedies" instead of their products. This advice against using citric acid to remove limescale was especially surprising for me: ...
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2answers
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Reaction mechanism of phenylhydrazine with carbonyl

I am currently working on the following problem, but I don’t know how it is solved: I guess it is a Fischer-Indol synthesis, but I am not sure. This is what I got: Any help would really be ...
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1 eq HCl will reduce carbon carbon double bond or triple bond? [closed]

Here I am not sure about the mechanism of the reaction. But I was thinking triple bond will have higher tendency to get reduced. But in the product only the double bond inside the ring is reduced and ...
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1answer
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Given type and number of carbon atoms and degree of unsaturation of a hydrocarbon, write structural formula

Write a structural formula of the hydrocarbon that contains 4 primary carbon atoms, 2 ternary carbon atoms, 3 quaternary carbon atoms, and has degree of unsaturation 3. This has been given at the ...
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Does changes in pH affects cyclic form of glucose in water solution?

Glucose in water solution is mainly in cyclic form. Both base and acid can catalize formation of hemiacetal, but in distinct mechanisms. I found information that monosacharides eg. glucose exist ...
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1answer
56 views

What are the resulting conjugate acid and base of phenol and 4-nitrophenol

I have to complete the equation 4-nitrophenol + phenol ---> and then label the acid, the base, the conjugate acid and the conjugate base. I think the answer ...
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1answer
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Why does the reaction of Brady's reagent and cyclohexanone not also form an enamine-type product?

In this reaction in a Khan academy video, cyclohexanone reacts with Brady's reagent to form hydrazone product. My question is why doea Brady's reagent + cyclohexanone not also form an enamine product ...
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Are Wacker oxidations tolerant of carbonyl groups?

I was wondering if there was anything in the mechanism of a Wacker oxidation that would interfere with ketones or aldehydes already present in the molecule. Ketones and aldehydes can't be oxidized any ...
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difficulty of de-protonating a vinylic halide

I'm confused as to why the second elimination of a dihalide to form an alkyne is so much slower than the first. It seems like the H on one carbon an X on another carbon would still align their ...
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Relationship between thermodynamics and steric hindrance in reaction outcomes?

I am investigating reactions with alkyl-substituted amines ($\ce{R} = \ce{Me}, \ce{Et}, \ce{^iPr}, \ce{^tBu}$) and a second reagent, in which product Z is formed. $\Delta G$ for all of these ...
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What is the protocol for esterification reaction between nanocellulose and tartaric acid?

I am trying to prepare nanocellulose esters via esterification with Tartaric acid. I know that the traditional method employs a strong acid such as sulfuric acid. What would the process look like in ...
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1answer
60 views

Racemization of hydrocarbon in presence of AlCl3

Our textbook mentioned that the compound in the diagram racemizes in presence of $\ce{AlCl3}$, but it didn't explain anything. Any help regarding the mechanism of the reaction would be appreciated.
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major product formed in wurtz reaction in the given molecule[ 1,3-dibromo-2,2-di(1-bromomethyl)propane ]

This is the reactant molecule which undergoes wurtz reaction. All possible products are- What will be the most favorable in all of these? In my opinion that the last one should not be the one because ...
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Chemical analysis of campholene nitrile

I have a problem. I am synthesizing an organic compound called campholene nitrile (2,2,3-trimethylcyclopent-3-en-1-ylacetonitrile). I need to analyze it. But there's a problem. I do not work for a ...
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Substitution of dihalo alkanes

Can I substitute 1,1-dichloropropane to get propane-1,1-diol? I'm just not sure if such a reaction would be correct.
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Will concentration of sodium hydroxide affect the result of chicken feather hydrolyzate if i don't standardized it?

The title of the paper: Isolation and characterization of keratin from chicken feathers https://doi.org/10.1063/5.0002792 Here is the method: Keratin was isolated by dissolving 5g of chicken feather ...
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1answer
58 views

Oxidation of tert-butyl alcohol with potassium permanganate

I was doing a high school lab, and according to my expectations for organic chemistry reactions, the following reaction of potassium permanganate and tert-butyl alcohol (t-butanol) should occur: ...
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1answer
53 views

Why pyrolysis of C6H10 doesn't give C5H10 + CH4 [closed]

In my book it's given pyrolysis of C6H14 gives C6H12 + H2 Or C4H8 + C2H6 Or C3H6+C2H4+ CH4 ( as it gives atleast one alkene) but there are other possible alkenes as well such as C5H10.
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How to determine if all carbon atoms in a cyclic compound lie on the same plane?

I'm currently doing a-levels chemistry and came across a question asking if all 17 carbon atoms in cyclic rings of a cholesterol molecule lie on the same plane. I've done some googling and it turns ...
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1answer
65 views

Order of basicity for arylamines and ammonia in gas phase

In aqueous solution, the basicity order is: $\ce{NH3 > Ph-NH2 > Ph-NH-Ph > (Ph)3N}$ What will be the order in gas phase? Following are some considerations: 1- In $\ce{NH3}$, $\ce{N}$ is $\ce{...
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1answer
29 views

Mechanism for hydrolysis of cyanohydrin [closed]

I know that acetals can be hydrolyzed with H2SO4 but I am not sure how benzaldehyde would be formed following hydrolysis of the cyanohydrin. When I searched online it I found answers suggesting that a ...
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1answer
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Boiling and melting points of hydrocarbons [closed]

What happens while boiling and melting hydrocarbons? Which bonds are broken? When we compare the boiling point (b.p.) and melting point (m.p.) of certain hydrocarbons the order is inverted. For ...

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