What should we know about dialkylcuparates? (Their application to the synthesis of ketones from acyl halides and by Michael addition. - GS).
This blog is a learning resource for undergraduate students studying organic chemistry. It consists of a database of actual questions and answers about organic chemistry collected by a chemistry professor teaching the subject.
Topics
- Halides-alcohols-ethers (94)
- Conjugation (60)
- Alkenes-alkynes (51)
- Carboxylic acid derivatives (39)
- Structure-bonding (39)
- Aldehydes and ketones (36)
- Alkanes-cycloalkanes (31)
- Stereochemistry (27)
- Spectroscopy (21)
- Acids-bases (19)
- Amines (18)
- Useful links (2)
Wednesday, April 22, 2015
Tuesday, April 21, 2015
Sunday, April 19, 2015
on reactivity of derivatives, I got the following answer for increasing reactivity toward nucleophilic acid substitution: sodium acetate, ethyl acetate, ethyl thioacetate, acetic anhydride, acetonitrile, acetyl chloride. I’m not sure if that is right. (Almost. Move acetonitrile in between sodium acetate and ethyl acetate - GS).
sodium acetate, acetonitrile, ethyl acetate, ethyl thioacetate, acetic anhydride, acetyl chloride (Yes - GS).
Can you explain why? (Acetonitrile has a strong triple bond, which is supposed to be broken by the nucleophile, so it is more reactive only than very unreactive negatively charged sodium acetate. Also there is no leaving group in acetonitrile, which pushes the reaction forward. - GS).
Thank you!
Saturday, April 18, 2015
this organic chem first semester stuff, but my friend just confused me and I just wanted to make sure that I understand this correctly ethylene is 2 C double bonded so 1,1,2,2-tetrachloroethylene would be 2 Cl bonded to a C=C which is bonded to another 2 Cl? Or is it just single bonded? (You are correct, It is Cl2C=CCl2 - GS).
Tuesday, April 14, 2015
Dr. Sereda, when a crossed Cannizzaro reaction occurs, how do you know which aldehyde is converted to an alcohol and which is converted to a carboxylic acid? (Methanal is converted to a carboxylate, and the other aldehyde is converted to an alcohol. For other aldehyde pairs, both scenarios occur, which makes the reaction unpractical. - GS).
Friday, April 10, 2015
Professor Sereda, I was briefly skimming over some of the newly made learning supplements and I was wondering if you could explain why we have the differences in acidity between the different classes of carbonyl groups (eg. aldehydes, ketones, carboxylic acids, amides, etc.) Thanks. (Additional stabilization of the carbonyl group by conjugation with a lone electron pair decreases its activity, which includes acidity, enolization, and electrophilicity. - GS).
Tuesday, April 7, 2015
I was hoping you help explain how we synthesize ethyl-isopropyl amine from acetone.. (Acetone is the source of the isopropyl group. Ethylamine is the source of the ethyl group. They react to form an imine, which is next reduced to the target amine. Same strategy will work for many other amines. - GS).
Wednesday, April 1, 2015
Why does a benzene ring with an electron acceptor group undergo addition first and then elimination? (Because of stabilisation of the anionic meisenheimer complex - GS). What happens if you have an electron donor group? (The reaction will proceed with a very strong base only by the benzyne mechanism - GS).
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