Upgrade to remove ads
Chapter 20 - All about AMINES
Terms in this set (12)
How many different ways to creates amines?
If you are starting with an Sn2 susceptible alkyl halide (R-X) what can you do to get a primary amine?
There are two methods:
- Gabriel's Synthesis --> use of N-alkyl-phthalimide with NH2-NH2 (hydrazine)
-Staudinger Reaction --> use of 1. NaN3 (to make alkyl azide), 2. Ph3P/H2O
If you are starting with a nitro compounds what can you do to get a primary amine?
There are multiple reagents
1. Fe, HCl
2. H2, cat. Pd/C
3. 1. LiAlH3, 2. H2O (harsh)
4. SnCl2, H2O (mild)
If you are starting with a nitrile (R-CN) what can you do to get a primary amine?
Use first step LiAlH4 followed by aqueous workup using water.
1. LiAlH4, 2. H2O
If you are starting with a carboxylic acid what can you do to get a primary amine?
Curtis Rearrangement --> the reagents or steps are
1. SOCl2 (carboxylic acid to acid chloride)
2. NaN3 (acid chloride to alkyl azide)
3. Heat (alkyl azide to azyl intermediate to isocyanate)
4. H2O (isocyanate to primary amine)
How can you came amines starting with an amide?
1. LIAlH4, 2. H2O
Primary amide --> primary amine
Secondary Amide --> secondary amine
Tertiary amide --> tertiary amine
Reductive Amination: Making Amines starting with an Aldehyde or Ketone and a source of Nitrogen (NH3, Primary amine, and secondary amine).
Reagent --> NaBH3CN, aq. EtOH pH =5-6
Nitrogen Source --> Amine Product
NH3 --> primary amine
primary amine --> secondary amine
secondary amine --> tertiary amine
Acylation ammonia, primary and secondary amines.
-Makes amides and it uses acyl chloride
-Primary amine makes secondary amide
Conversion of Primary Aromatic Amines to aromatic diazonium salts
You start with a PRIMARY aromatic amine and react with NaNO2 and HCl which produces the diazonium salt
With how many reagents can the diazonium salt react, list them and the product.
It can react with 7
1. CuBr, N triple N- is substituted by Br
2. CuCl, places a Cl
3. KI, places an I
4. HBF4, places a F
5. CuCN, places a CN
6. CuO3, Cu(NO3)2, H2O, heat, places an OH
7. H3PO2, places a H.
Relevance of the reaction between a diazonium salt H3PO2.
-H3PO2 replaces the N triple N- with a Hydrogen
-Often this allows for a Phantom Group
Making Azo dyes
-> Produced by using aniline or phenols derivatives and reacting it with aromatic diazonium salts in basic conditions (ph = 8=10) and a follow-up step of neutralization (this is for the phenols because we need the OH, O to be more reactive)
-> For aniline derivatives acidic conditions are fine.
->If the pH is too high it destroys the diazohydroxide
OTHER SETS BY THIS CREATOR
Scrivas Binder Medical Terminology
Chapter 17- All about CARBOXYLIC ACID and FAM (EST…
Chapter 16 - All about ALDEHYDES and KETONES
C-13- NMR Spectroscopy
OTHER QUIZLET SETS
Research exam 2 study guide
Pharm FINAL (lecture example questions)
CHP 18: Managing Performance