The purposeful execution of chemical reactions to obtain a desired product.

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Oxidation of acetophenone to benzoic acid

According to the solutions manual, the oxidation of acetophenone to benzoic acid can be achieved through addition of chromic acid and application of heat. The solutions manual refers me to a section ...
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1answer
21 views

Permanent Balloon?

Is it possible to create a container for helium that it can't permeate through, like a permanent balloon? Or, if not, what kind of material would have the lowest permeability for that application? I ...
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1answer
102 views

Diels-Alder rate of reaction

Why is cyclopentadiene more reactive than 9-anthracenemethanol when acting as a diene? Both molecules are locked in an s-cis conformation, which is favourable. I'm thinking that it's due to the ...
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1answer
46 views

How do I synthesize 3-phenyl oxirane-2-carbaldehyde from chloroacetonitrile?

I start with the hydrolysis of the nitrile in carboxylic acid and esterification of this. After I use the Darzens' reaction (using benzaldehyde), then I reduce the ester function with DIBALH in ...
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1answer
41 views

Intramolecular hydrazide condensation

Say I have the compound $\ce{CH3CONHNH2}$. Is it possible, that when I add an acid, an intramolecular condensation reaction occurs, forming the cyclic compound: Furthermore, in general, the ...
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1answer
42 views

Grignard formation and vicinal dihalides

So let's say I have a symmetric 1,2-dihalide (the halides are identical) and I wanted to make a Grignard and I only add 1 eq. of magnesium metal ... Will I get 1 eq. of asymmetric Grignards (i.e. ...
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1answer
44 views

Dialkylation reactions

In the synthesis of ethyl 2-benzyl-2-methyl-3-oxobutanoate, is the nucleophilic substituion of a benzyl (chloride) group an Sn1 reaction? The experiment is conducted in ethanol (protic) and is under ...
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1answer
67 views

Thionyl Chloride and enols, carboxylic acids, alcohols

Propanol + SOCl2 -> Expected alkyl halide product. Propanoic acid + SOCl2 -> Expected acid chloride product. Acetone enol + SOCl2 -> doesn't work in the expected manner. My prof says the SOCl2 ...
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1answer
40 views

How do I synthesize 3-hydroxydihydrofuran-2-one from formaldehyde?

I want to synthesize 3-hydroxydihydrofuran-2-one from formaldehyde but I do not know of a method. I tried a Mannich reaction and lactonization after dehydration.
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1answer
50 views

What type of organic compounds are used in OLED technology?

I know that there are organic compounds that exhibit electroluminescence, and are those types of materials difficult to synthesize?
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76 views

P-phenylenediamine Production Process

How p-phenylenediamine (PPD) is produced? PPD is used as raw material for Kevlar (Para amid Fiber).
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1answer
39 views

Friedel-Crafts synthesis - How is HCl produced?

In the mechanism for the acetylation of bromobenzene, how is $\ce{HCl}$ gas produced? The reactants are acetic anhydride, bromobenzene, $\ce{AlCl3}$ and dichloromethane. Initially, ...
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85 views

Acetylation reaction

In the Friedel - Crafts acetylation of bromobenzene, how is it possible to obtain a black-coloured product? When the acetic anhydride was slowly added to the reactants - $\ce{AlCl3}$, DCM, ...
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1answer
114 views

Synthesis of 2-Phenyl-2-Butanol from Grignard Reagent

The question is this: 2-Phenyl-2-Butanol can be synthesized by three different combinations of a grignard reagent and a ketone. Show each combination. I can only think of one. Butanone with ...
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1answer
166 views

Synthesis of 4-iodonitrobenzene

I was trying to synthesize 4-iodonitrobenzene in the lab today - however, the appearance of my product really confused me. At first, I added conc. sulphuric acid to water and 4-nitroaniline. This ...
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1answer
38 views

Why don't we use an alkyl halide directly in Gabriel Phthalimide Synthesis?

In Gabriel Phthalimide Synthesis, why do we use $\ce{KOH}$ in first step rather than directly adding an alkyl halide?
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1answer
41 views

How is the process of creating PVC fabrics harmful for the environment?

I often hear that the production process for PVC fabrics (such as those used in Gucci and Versace handbags) is very harmful to the environment. What part of the process is harmful and can this be ...
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0answers
75 views

What compound can give off heat when it comes in contact with ice?

What compound is able to produce heat when it comes in contact with ice? The compound has to be able to produce heat multiple times. I was thinking of a compound that is similar to Calcium Chloride. ...
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1answer
32 views

Electrolysis used to cause a Chemical Reaction?

Electrolysis is used to separate compounds like Water into Hydrogen and Oxygen. Can it be used to induce a synthesis reaction rather than splitting reactants apart? For example, could you use ...
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1answer
54 views

Product of pyridine with acetic anhydride and acetic acid.

I have a reaction for acetylation of lignin with pyridine and acetic anhydride. I need to know, what's the product of reaction between pyridine and acetic anhydride and acetic acid.
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1answer
38 views

Lewis Acid Catalysts [closed]

I am studying for the International Chemistry Olympiad and some of questions involve synthesis of complicated organic compounds and i have no idea how to do them. The setting of the questions is ...
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2answers
3k views

Why are there no cheap diamond equivalents?

We recently learned in school that diamonds sparkle as the are very optically dense, meaning that it takes longer for light to pass through them, thus meaning that the light totally internally ...
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93 views

Organic synthesis problems

I am an A-level student going into university and I am looking for a source of organic synthesis problems and answers that is freely available on the internet. The difficulty level I am looking for is ...
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1answer
52 views

What's wrong with tin?

I just read this In the Pipeline post and I was slightly confused by a statement on the use of tin. Lowe reports on this paper, which describes a synthetic route to spiro heterocycles using tin ...
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1answer
33 views

What is a sacrificial agent?

I came across this reading a journal article. Here I have the context: Here we report for the first time the synthesis of $\ce{TiO2}$ NPs on a layered $\ce{MoS2}$/graphene (MG) hybrid for use in ...
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2answers
207 views

Cyclohexane to cyclopentane synthesis

Does this route work? 1) Free-radical halogenation. 2) Elimination with strong base to form cyclohexene. 3) Ozonolysis to make di-aldehyde. 4) Oxidation to make di-carboxylic acid. 5) ...
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1answer
61 views

Could you suggest me a good coupling method for amide synthesis between tetrahydroisoquinoline and a carboxylic acid?

I want to synthesize an amide using tetrahydroisoquinoline and an unsaturated carboxylic acid which is light sensitive. I tried using DCC as coupling agent and DCM as the solvent at room temperature , ...
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0answers
108 views

What are the specific disadvantages of using a bio-catalyst (called Lipolase) in the synthesis of the drug pregabalin?

I am studying the synthesis of a drug pregabalin, for which both chemical and bio-catalysts are used. Using a biocatalyst is way better than chemical route, as explained here. In fact, The invention ...
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1answer
48 views

Creation of ester from acetylene derivative

I took a much different approach from the solutions manual. My synthesis: 1) H2 and Lindlar's catalyst to stop at the alkene. 2) Oxidative cleavage to form benzoic acid. Works here because we ...
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1answer
20 views

Equivalencies and catalytic hydrogenation

Can we actually control catalytic hydrogenation by introducing specific molar quantities of hydrogen gas? My prof insists on no. No we cannot use a certain equivalency of hydrogen gas to stop at a ...
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1answer
37 views

Resonance and reductions with sodium borohydride

I know that sodium borohydride doesn't work particularly well on resonance-stabilized carbonyl groups (i.e. esters) but what about this carbonyl in the center of the above picture? This appears to ...
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2answers
137 views

Designing synthetic route to dicarbonyl compound

Sorry, not great at formatting. Here's the link in case the picture doesn't show up. http://imgur.com/axfUw25. It's the last one, where 1,4-dimethylcyclohexane breaks apart into...something. ...
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1answer
75 views

Decarboxylation under acid, water, and extreme heat

I am asked whether dimethyl malonate or methyl acetoacetate decarboxylate when hit with acid, water, and extreme temperatures. I believe the answer is both because both are esters, and esters, upon ...
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1answer
106 views

Synthesis of Pseudopelletierine, Mannich reaction base catalysed

The synthesis of Pseudopelletierine starts from glutardialdehyde, which reacts with methylamine and acetonedicarboxylic acid in a two-fold Mannich reaction. This is the reaction: I need to write ...
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1answer
38 views

Formation of methyl esters

Can't we perform Fischer esterification using methanol to make a methyl ester from a carboxylic acid? If so, why might we use diazomethane? Would the release of nitrogen gas confer an entropic ...
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162 views

Wittig reaction with benzaldehyde

Somehow I am told that my product is incorrect. Why is my product incorrect? As far as I can see this is a Wittig reaction resulting in a two carbon increase with removal of the oxygen. The only ...
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2answers
87 views

Can imines be catalytically hydrogenated?

Can imines be catalytically hydrogenated? According to the DEA this appears to be possible. However I cannot find any other references to catalytic hydrogenation of imines anywhere else. ...
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2answers
141 views

Reductive amination of (protected) 3-Oxopropanenitrile: Will azetidin-2-ol be formed via intramolecular ring closure?

What happens during this reductive amination? I got the first product; the lithium aluminium hydride will reduce the nitrile to an amine. But what about the reductive animation step? As far as I can ...
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1answer
53 views

Why gives NaBH4 more Felkin-Anh product than LiAlH4 gives?

In lecture we discussed the nature of the nucleophile for the attack of the carbonyl. LiAlH4 acts as a better nucleophile (hydride) than NaBH4. I know there is no hydroboration! So I would have ...
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2answers
82 views

Sodium cyanoborohydride and iminium reductions

I understand that the LAH will reduce the nitrile into a primary amine. The addition of acid will likely destroy the acetal mask and leave us with ethylene glycol and a molecule with both a ketone ...
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1answer
30 views

Synthesis; effect of hydrogen gas and platinium

I'm pretty sure the last step in there is just something to throw us off. From what I understand, the first step will give us a Grignard, which will attack the carbonyl in formaldehyde to give us a ...
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1answer
89 views

Phenol protection

Would an acceptable way to protect a phenolic alcohol be through a Williamson ether synthesis? As in: 1) Deprotonating phenol with sodium hydroxide. 2) Addition of methyl iodide. 3) Deprotection ...
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59 views

Mechanism for hydroxyethylation on nucleobases (e.g. Thymine)

I'm trying to figure out the following reaction mechanism There's a reference paper by Yanagi and Akiyoshi(1959) showing the hydroxyethylation of imides resulting in the following I have two ...
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2answers
95 views

Is it possible to create a 100% identical copy of a chemical?

For example a 100% identical copy of vitamin A, same shape, same formula, same structure.
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199 views

Synthesis of benzophenone

Would his be a valid synthesis? I'm just unsure about the oxidative clevage step. I know that there is a Benzylic hydrogen. So should oxidative clevage work here? What happens to the fragment that is ...
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1answer
77 views

Synthesis of synthetic detergent with Friedel Crafts Acylation

I propose the following synthesis. 1) Oxidation of aldehyde to a carboxylic acid. This sets me up for FC acylation once I ... 2) Attack the -OH with thionyl chloride ad form the acid chloride. 3) ...
3
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1answer
106 views

Simple experiments involving enantiomer synthesis

I want to do an experiment to investigate factors affecting the synthesis of chiral molecules. The only problem is, my institution doesn't have much money, and it seems like the chemicals required for ...
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121 views

Synthesis of 1-hexene from 1-octyne

This is my synthetic pathway. For one, is it plausible? For another, is it efficient? 1) Reduction of 1-octyne with hydrogen gas and Lindlar's catalyst to 1-octene. 2) Oxymercuration to install a ...
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3answers
321 views

Carbon decrease from 1-octyne to 1-hexene

I am to turn 1-octyne to 1-hexene. Method 1 1) Reduction using sodium metal in pure ammonia to an alkene. 2) Halohydrin formation; the -OH installs at the more substituted carbon due to its ...
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Pedagogical exercise - How to synthesize methamphetamine

I am asked to synthesize "methamphetamine." Note that there is no configuration designated for this molecule, and methamphetamine refers to a very specific configuration. In any case, here are the ...