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9 votes
3 answers
551 views

Synthesis of racemic nicotine

In my advanced organic chemistry course, we were asked to fill the following scheme for the synthesis of racemic nicotine, starting with ethyl nicotinate: Exercise 6: Complete the following scheme ...
Mäßige's user avatar
  • 383
4 votes
1 answer
107 views

Compatibility of DCM/CCl3 with sodium hydride

In our undergraduate studies we were told that chlorinated solvents should not get in contact with alkaline elements like sodium, potassium etc., due to the violent reaction that will form the ...
raptorlane's user avatar
3 votes
0 answers
50 views

What is the difference in reactivity between the various borates (trimethyl, triethyl, triisopropyl borate) to form boronic acids?

For the transformation of 1,3-dibromobenzene to bromobenzene boronic acid, different groups use different boration reagents namely trimethylborate, triethyborate and triisopropylborate). The reaction ...
The Red Man Jolan Bonelli's user avatar
2 votes
2 answers
257 views

Should I remove inhibitor from methyl acrylate?

I need to run multiple aza-Michael additions of methyl acrylate with various amines (dimethylamine, benzylamine, phenylethylamine, aniline, etc.) in order to get the bis-ester. I was wondering if the ...
Matt's user avatar
  • 21
0 votes
0 answers
72 views

Find the missing chemical structures in the reaction sequence

I came across the following question, where a set of reagents are used, starting from a carbohydrate derivative. I understand that this is some total synthesis reaction, but I cannot find which one. ...
Cyclopropanol's user avatar
5 votes
1 answer
267 views

Selective formation of enolates

I saw the following reaction on Modern methods of Organic Synthesis by Carruthers. The reaction is about the selective alkylation of trimethylsilyl enolates, and is shown below. However, I have some ...
Cyclopropanol's user avatar
2 votes
2 answers
329 views

Are these reactions in synthesis of melamine correct?

I found the Wikipedia article for melamine to be incorrect in "synthesis and reaction" section; so I decided to edit it. But on the other hand I'm not sure my assumption to be correct that ...
Walter Heisenberg White's user avatar
0 votes
1 answer
285 views

What are the reactions between Zinc acetate dihydrate and Methoxyethanol? [closed]

I am synthesizing a sol-gel solution with Zinc acetate dihydrate + Methoxyethanol and ethanolamine as stabilizer, and I wonder what are the reactions that are taking place in the process. Could you ...
Chemistry's user avatar
1 vote
1 answer
97 views

Why is the sp3-sp3 reductive elimination between the R1 and norbornene in the Catellani Cycle ''not favorable''?

I have recently started reading a book about C-H activation and I cannot figure out why in the Catellani reaction cycle the R1-norbornene reductive elimination side reaction which can be a major issue ...
TheBorcanu's user avatar
-2 votes
1 answer
431 views

What does it mean stir at room temperature overnight? [closed]

It was mentioned in synthetic procedure to "stir at room temperature overnight". What does this mean? (I want the exact duration for how long should I keep stirring.) How is it possible to ...
Dina's user avatar
  • 7
1 vote
1 answer
423 views

Reduction of unsymmetrical ketones using BINAL-H (Enantioselectivity)

I am struggling with a problem regarding the enantioselectivity of BINAL-H for quite some time now. The reaction scheme shows the reaction with (S)-BINAL-H as it is observed plus the transition state ...
marsem's user avatar
  • 21
3 votes
0 answers
42 views

Does the halogenation of an alkane also produce haloalkanes of a longer chain length?

Take a typical halogenation of an alkane reaction (the bromination of methane). $$\ce{Br_2->Br· + Br· (in the presence of UV light)} $$ $$\ce{Br· + CH4->·CH3 + HBr} $$ One of the possible ...
tai's user avatar
  • 39
0 votes
0 answers
39 views

Preparation of m-nitroaniline from m-dinitrobenzene [duplicate]

Consulting various Organic Chemistry resources, I have found two reactions for the purpose stated in the subject: First reaction: Second reaction: But, I cannot find the reaction mechanism by which ...
Carlos's user avatar
  • 607
6 votes
1 answer
224 views

Does the Oxy or Alkoxy Claisen Rearrangement Exist?

@Waylander's cogent Comment to the query of @Random Guy inspired me to post a problem in synthesis to test a question I have pondered for some time. The activation energy (AE) for the Cope ...
user55119's user avatar
  • 17.2k
5 votes
2 answers
364 views

How can we synthesize this cycloester, starting with methyl 4-phenylbutanoate?

I was wondering how to realize following synthesis: I am struggling with this one; for sure, this has something to do with the benzyl position which is particularly reactive, and something ...
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