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Chapter 17- All about CARBOXYLIC ACID and FAM (ESTERS and AMIDES)
Terms in this set (16)
What is Nucleophilic Substitution at Acyl Carbon?
-This is a reaction between the acyl carbon such as acyl chloride with a nucleophile (such as NaOR)
-Reaction is an addition of the nucleophile to a reduction by removing the original halide.
How many different ways can you prepare carboxylic acids?
Starting with a primary alcohol how can you make carboxylic acid?
-By using Jones Reagent
-Reagent: CrO3, H2SO4
-Oxidation of primary alcohol
Starting with a methyl benzene how can you make benzoic acid?
-By oxidation of methylbenzene
-By using the reagent --> 1. KMnO4, aq. OH, heat, 2. H+
Starting with CO2 how can you make carboxylic acid?
-You can use Grignard Reagent followed by acidification
-Reagents: 1. R-MgBr, 2. H+
Starting with an aldehyde how can you make a carboxylic acid?
-By using reagent PDC (pyridinium dichromate) in aq. DMF
How can you can make carboxylic acid starting with a nitrile (R-CN)
-Through hydrolysis using either aq. H+ or aq. -OH
-The acid is more commonly used
-The intermediate is a primary amide
-The byproduct is an ammonium salt
How many different ways can you prepare esters?
Starting with an acid chloride how can you make an ester?
-By reacting the acid chloride with an alcohol.
-The byproduct is HCl
Starting with carboxylic acid how can you make an ester
-You can do it through two different ways
-FIRST:Esters by Fisher Esterification
--> Starting material: carboxylic acid and alcohol
--> Reagent: HCl
--> Product: Ester and H2O
--> This reaction can be harsh if the starting material contains functional groups that are sensitive to acid.
-SECOND: Esters by Reaction of Carboxylic acid with alcohol in the presence of DCC.
-->Starting material: Carboxylic acid and alcohol
--> Reagent: DCC (dicyclohexylcarbodiimide - this is a dehydrating agents) (mild)
--> Product: Ester and something that looks like a double amide lol
How many different ways can you prepare amides?
Starting with an acyl chloride how can you make an amide?
-Starting Material: Acyl chloride with NH3 or 1º amine or 2º amine.
-When this reacts it is similar to a nucleophilic substitution at the acyl carbon.
Starting with carboxylic acid how can you make an amide?
-Starting material: carboxylic acid and 1º amine or 2º amine
-Product: Amide; if using 1º amine --> 2º amide, and using 2º amine --> 3º amide.
What reagent do you use to prepare nitriles (R-CN) from 1º amides?
P2O5 which it is a dehydrating agent.
Recommended textbook explanations
Organic Chemistry (Loose-Leaf), Sapling Learning Online Homework (without eText) 12-month access card, Study Guide/Solutions Manual for Organic Chemistry
K. Peter C. Vollhardt, Neil E. Schore
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