Glossary of Organic Chemistry Ch. 19 of Wade (sec. 1-18, amines)
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- R-Br + ammonia (excess)
(ammonia is the nucleophile in an SN2 mechanism)
- acid chloride + amine?
R-CO-Cl + R'-NH2 --> ?
Don't forget to deprotonate the N+ with another amine.
- Carboxylic acid to an acid chloride?
R-CO-OH -(?)-> R-CO-Cl
- SOCl2 (Thionyl chloride)
- amine + sulfonyl chloride?
R'-NH2 + R-SOO-Cl --> ?
- amide -(?)-> amine + c. acid
R2N-CO-R' -> R2N-H + R'COOH
- H3O+ and heat (hydrolysis)
- R-NH2 + NaNO2 + 2HCl-->
- diazonium salt
- Ar-N2+ to Ar-OH
- Ar-N2+ to Ar-Br
- Ar-N2+ to Ar-Cl
- Ar-N2+ to Ar-CN
- Ar-N2+ to Ar-F
- Ar-N2+ to Ar-I
- Ar-N2+ to Ar-H
- Ar-N2+ to Ar-N=N-Ar'
- H-Ar' (Ar' is activated)
- Which is more basic, pyridine or piperidine?
The sp3 electrons of piperidine are held more losely than the sp2 e- of pyridine. (1/4th vs. 1/3rd s-character)
- Which is more basic, pyrrole or pyridine?
- Pyridine. The electrons in pyrrole are involved in the aromatic ring and are unavailable to be donated.
- E2 elimination of a quarternary ammmonium hydroxide will give the ____ ___________ alkene.
- least substituted / terminal
(the Hofmann product)
- The reagents to convert a tertiary amine into an amine oxide for a Cope elimination.
- 1) Peroxide
(H2O2 or MCPBA or R-COOOH)
- Steriochemistry for a Cope elimination.
- Syn. The cyclic transition state puts the N+ and H in the same plane on the same side.
- Steriochemistry for a Hofman elimination.
- Anti. The anti-coplanar arrangement of the N+ and H is required for E2.
- Amine + HCl -->
- ammonium salt (now soluble in the aqueous layer)
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