Applies to long and complex natural product syntheses as much as to short one or two-step syntheses. This also covers synthetic problem sets and retrosynthetic analyses. Should not be applied to simple reactions such as the formation of hydrogen by acidic oxidation of metals.

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25 views

Is it possible to selectively add one hydroxyl group to this compound? [duplicate]

It needs to be available to go on to form an ester linkage with another compound containing an acid group. I don't want to alter the compound I just want to be able to create a linker.
0
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1answer
59 views

Introducing a hydroxyl group to this compound [on hold]

Is it possible to selectively add one hydroxyl group to any of the ring positions of this compound? It needs to be available to go on to form an ester linkage with another compound containing an acid ...
1
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1answer
27 views

Acetaldoxime Synthesis: Hydroxylamine vs Hydroxylamine HCl

Wikipedia says acetaldoxime can be prepared by reacting Acetaldehyde & Hydroxylamine in the presence of NaOH. https://en.wikipedia.org/wiki/Acetaldoxime But the reaction shown uses Hydroxylamine ...
2
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2answers
87 views

3-step process to make propyl ethanoate from propene

I was asked to make propyl ethanoate from propene in three steps. I have access to the reactions below. Nucleophilic substitution (Both SN1 and SN2) Electrophilic addition Hydrogenation Dehydration ...
0
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0answers
27 views

How can I create crotonaldehyde using only mineral reactants?

I tried using alkylation to get the correct chain lenght, but I can't find a way to create the double bond. I'm a total novice at chemistry, so please forgive my ignorance.
5
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2answers
67 views

Hock rearrangement of hydroperoxides

Which hydroperoxides undergo a Hock rearrangement? e.g. Cumene hydroperoxide undergoes a Hock rearrangement to yield acetone and phenol Would the following hydroperoxide of ethylbenzene also ...
1
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1answer
27 views

Is this mechanism for the formation of a tosylate correct?

I've been given this mechanism by my lecturer for the formation of a tosylate. It claims that NEt3 is needed to remove the hydrogen from the O+ in the second step. However surely the Cl- from TsCl ...
1
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1answer
50 views

Conversion of 4-nitrotoluene to 2-bromobenzoic acid [closed]

In the above conversion why doesn't bromine add to methyl group? Is the first reaction following free radical or polar reaction (Friedel-Crafts). If it's following free radical mechanism then Br ...
3
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0answers
36 views

What is the mechanism of synthesizing hydroxybenzotriazole?

I have big problem with this reaction. Is this nucleophilic substitution? Cl is removed by hydrazine? It's my only idea, I don't know if this mechanism below is correct for this example:
3
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1answer
79 views

Do Grignard reagents deprotonate amines?

Can I add Mg/dry ether to 2,4,6-tribromoaniline followed by $\ce{D2O}$ in order to replace the bromines with deuterium? The reaction I'm proposing is part of a synthetic route as shown below.
1
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0answers
29 views

Suzuki Coupling of 2,4-dichloropyrimidine with boronic acid

Why does the Suzuki coupling reaction occur at 4-Cl, but not 2-Cl position??
0
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0answers
19 views

Acetic acid synthesis

I made some acetic acid by bubbling ethenone through water, but my weight calculations don't make any sense, so I think there were some side products along with the acetic acid. What are they, and ...
3
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1answer
47 views

Synthetic options for selective hydroxylation at terminal position

Are there any synthetic options to add a hydroxyl group at the terminal position to the bicyclo compound below? What might be reactions worth trying, any idea? Or is this a lost cause?
2
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1answer
13 views

Is this amide compound electrophilic enough to be attacked by a cyclopentadiene in base?

I am trying to make a fulvene molecule with dimethylamino and phenyl substituents. My worry is that the amide group donates electron density into the carbonyl carbon making it less electrophilic.
0
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0answers
13 views

How to deodorize pyrrolidone derivatives such as n-vinyl pyrrolidone (NVP) and n-methyl pyrrolidone (NMP)?

After catalytic preparation of NVP through dehydration reaction, the product smells a bad odor. This is also occur for NMP production and the odor is like a dead fish odor! how to deodorize these ...
3
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0answers
40 views

Benzyl (3,4-difluorophenyl)carbamate reaction with epoxide in basic conditions

I attempted this mechanism, however I am uncertain if I am correct. Any guidance for this problem would be appreciated!
4
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1answer
64 views

Synthesis of indigo from anthranilic acid - reaction not taking place

I was trying to synthesise indigo via the Heumann indigo synthesis (II.), which involves heating antrhanilic acid and chloroacetic acid, both dissolved in isopropanol. After heating up, a hydroxide or ...
4
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1answer
64 views

Synthesis of 3-Methylenecyclopentene from 1-methylCyclobutene [closed]

How do I make 3-Methylenecyclopentene from 1-methylcyclobutene? I thought to do ring opening reaction to add 1 carbon atoms but this won't add double bond in product. How to start please?
2
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0answers
42 views

Synthesis from cyclic ketone to alcohol

How can I make the product in the picture below from cyclohexanone? I did Stork enamine synthesis, but it results in terminal primary alcohol. I need secondary alcohol with one more carbon atom at ...
1
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0answers
29 views

Making benzoyl chloride - yellow liquid and a precipitate?

I am attempting to produce benzoyl chloride from benzoic acid (I need to convert an isotopically labeled version, so I can't just buy the acyl chloride). I am reacting benzoic acid with excess oxalyl ...
8
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1answer
68 views

How can I tell which parts of this example drug are necessary parts of its pharmacophore?

$\hspace{10mm}$ $\hspace{10mm}$(Click image for larger version) This picture identifies a generic drug-enzyme complex taken from an exam script. There is no name given. One part of the exam question ...
0
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0answers
44 views

Website/software guide in synthesis of organic molecules

Does any one knows any good website/software that helps in synthesizes of low molecular wight ligands. (I mean helps you in synthesis pathway design , optimization of pathways or even just give you ...
0
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0answers
19 views

Perovskite reaction equation (KMnF3)

For the synthesis of $\ce{KMnF3}$ I said the reaction equation was $\ce{3KF + MnCl2 -> KMnF3 + 2KCl}$ Is it this simple or are am I missing something with these particular types of reactions?
5
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3answers
118 views

Making o-Bromoaniline from Aniline

How can I make o-Bromoaniline from Aniline(as a major product) ? I know how to make p-Bromoaniline from aniline, by acetylation followed by treatment with $\ce{Br2}$\ $\ce{CH3COOH}$ and hydrolysis. ...
3
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1answer
105 views

Side Products of Dow's process

In Dow's process of manufacture of phenol, $\ce{PhCl}$ is fused with $\ce{NaOH}$ at high temperature and pressure. What are the possible side products? And what is the intermediate formed? I think ...
5
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2answers
53 views

Farnesyl Diphosphate: Chemical commercial synthesis

Are there any practiced commercial routes for the synthesis of "farnesyl diphosphate"? I'm especially interested in options that would scale to industrial scale processing. To add some context, ...
0
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0answers
25 views

Biosynthesis of Xanthoxylin

Anyone can find a source for or explain the biosynthetic pathway for Xanthoxylin? It's the last practice problem I have for an exam, and I just can't seem to find info on it. Thanks!
4
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2answers
137 views

Synthesising Complex Aromatic Compound

I have to synthesis the above compound using only toluene as the carbon source. I have never done something like this before and I have no clue on how to start. I am even more confused by the fact ...
2
votes
1answer
60 views

Simpler synthesis?

I have to obtain 1-nitro-2,4,5-triaminobenzene from 1,3-dichlorobenzene. I have thought of: Reaction with $\ce{Mg}$ Rc with $\ce{CO2}$, then $\ce{H2O}$. By this point I have izophthalic acid. ...
1
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0answers
66 views

Making 1,3,5-Tribromobenzene from Phenol

The problem was to make 1,3,5-Tribromobenzene from Phenol. I thought to do it the following way: React phenol with $\ce{Br2/H2O}$. Then add $\ce{Zn}$ dust to get the product. Now I am in doubt ...
1
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1answer
70 views

Making N,N-Dimethylaniline from Aniline

Can I make N,N-Dimethylaniline from Aniline just by reacting it with $\ce{CH3X}$ ? According to me the lone pair of Nitrogen in Aniline is just not nucleophilic enough (since it is in conjugation ...
5
votes
1answer
51 views

is it possible to make ethanol from ethane through a chlorination / hydrolysis two-step procedure?

$\ce{C2H6}$ is chlorinated in presence of sunlight to form $\ce{C2H5Cl}$ and $\ce{HCl}$. $\ce{C2H5Cl}$ is then reacted with water to form $\ce{C2H5OH}$ + $\ce{HCl}$
1
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1answer
54 views

A question about preparation of chlorobenzene

The best method (as I have read) for preparation of chlorobenzene is by reacting it with $\ce{Cl2}$/$\ce{FeCl3}$. Why its not the best practice to react phenol with $\ce{PCl5}$ ?
3
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1answer
62 views

How do I convert 4-(Methylthio)benzaldehyde to 4-(thioacetate)benzaldehyde?

Sorry if I have the incorrect name of the final product. I'm trying to acylate the methyl mercaptan substituent to a thioester (thioacetate). I appreciate any help!
7
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1answer
64 views

Hiyama vs Sonogashira coupling

Why is Sonogashira's coupling more feasible than Hiyama's coupling when both could occur? I have seen many examples in syntheses, here is one (the penultimate reaction):
0
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0answers
63 views

Synthesis of Polyvinylidene fluoride (PVDF)

I would like to know what the easiest way of synthesising PVDF is, or is it easier to buy the polymer online, and could PVDF be made transparent. Thanks
4
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2answers
94 views

Method to synthesize KAu(CN)2 (or KCN)?

Every reasonably effective method of electroplating $\ce{Au}$ onto another metal's surface (e.g. $\ce{Cu}$,$\ce{Ni}$,$\ce{Ag}$, etc.) involves use of $\ce{KAu(CN)2}$ or in some cases $\ce{KAu(CN)4}$ ...
4
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1answer
119 views

How to synthesise 2-aminoethyl benzene

Starting with benzene, describe the synthesis of 2-phenylethan-1-amine providing all the reagents and conditions. I am not really great at organic chemistry and my knowledge is pretty limited. ...
0
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0answers
46 views

Argireline: Acetyl Hexapeptide 3 - Harmful cosmetics?

Background I came across a friend that told me about Jeunesse Global he has started working with. This company (multi level marketing) sells cosmetic products that seem to be not really in line with ...
0
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0answers
60 views

KMnO4 Oxidation of Methyl Group Attached to Nitrogen

Is it possible for a methyl group directly attached to a nitrogen atom in a non-aromatic compound $\left(\ce{-N-CH3}\right)$ to be oxidized using $\ce{KMnO4}$ in acidic medium to form a corresponding ...
7
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0answers
86 views

Enolate formation in cis/trans decalin

What will happen in the following reactions? I thought that after OH is converted into a good leaving group OTs, an enolate would be formed which would attack $CH_2OTs$, but the obtained structure ...
1
vote
2answers
78 views

Suggestions for reaction conditions to prepare methyl 2,4,6-trimethylbenzenesulfonate

I'm a beginner in organic chemistry and I wish to produce methyl 2,4,6-trimethylbenzenesulfonate. My reactants are 2,4,6-trimethylbenzenesulfonyl chloride (solid crystals) and methanol (solvent as ...
5
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0answers
81 views

What is the product after treating ethene successively with chlorine and water, sulfuric acid, and potassium hydroxide?

Question: Ethene reacts with $\ce{Cl2}$ in $\ce{H2O}$ to form A. A on reaction with $\ce{H2SO4}$ followed by heating gives B. B on reaction with alcoholic $\ce{KOH}$ gives C. Find C. My ...
1
vote
1answer
365 views

Corey -House synthesis vs Wurtz reaction

In Corey House synthesis the first step is formation of Alkyl Lithium. why can't we react alkyl lithium with alkyl halide to produce alkanes. Rather we choose to prepare Gilman's reagent? Does it have ...
7
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2answers
116 views

Simple method to lengthen alkane?

I'm working on a science project which involves the production of methane. I would like to be able to use the methane as fuel in (e.g.) cars (using octane) or gas tanks (using butane and propane) etc. ...
3
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1answer
51 views

Is this structure make-able?

I was wondering if it would be possible to make this chemical?
4
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1answer
791 views

Why is the Friedel-Crafts alkylation of nitrobenzene disfavoured?

Suggest a synthetic route to m-nitrotoluene, starting from benzene. The conversion can be achieved in two ways: $\hspace{10 mm}$ or: However, the first route is not possible as the ...
6
votes
2answers
174 views

Synthesize acyl chloride from aldehyde

I know it is usually easier to go from an acyl chloride to an aldehyde, but is there a way to synthesize acyl chlorides from an aldehyde? Edit: Upon some textbook reading (Wiley: Organic ...
2
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1answer
46 views

Using UV-C (254nm) light to cleave the amino acid off of vyvanse

Vyvanse: Desired product: Amide bonds absorb in the region of about 190 to 240 nm, so could using UV-C light conceivably cleave the amide bond? Also I don't think this reaction is as simple ...
2
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1answer
69 views

Tips for Improving Synthesis

I have already asked a similar question on titrations before. In a few months, I have a test on chemical synthesis. It is marked on the percentage yield, purity and crystal size of the product. I do ...