lecture 18 - Carboxyl Derivatives In this chapter, we study...

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Functional Functional Derivatives of Derivatives of Carboxylic Acids Carboxylic Acids Carboxyl Derivatives Carboxyl Derivatives ± In this chapter, we study five classes of organic compounds Cont. on next slide Carboxyl Derivatives ± In this chapter, we study five classes of organic compounds Structure: Acid Halides Structure: Acid Halides ± The functional group of an acid halide is an acyl group bonded to a halogen the most common are the acid chlorides to name, change the suffix -ic ic acid acid to -yl yl halide halide CH 3 CCl O Cl O O O Benzoyl chloride Ethanoyl chloride (Acetyl chloride) Hexanedioyl chloride (Adipoyl chloride) O RC- An acyl group Sulfonyl Chlorides replacement of -OH in a sulfonic acid by -Cl gives a sulfonyl chloride SOH H 3 C O O SCl H 3 C O O p- Toluenesulfonic acid Toluenesulfonyl chloride (Tosyl chloride, TsCl) 3 O O 3 O O Methanesulfonic acid Methanesulfonyl chloride (Mesyl chloride, MsCl) Acid Anhydrides Acid Anhydrides ± The functional group of an acid anhydride is two acyl groups bonded to an oxygen atom the anhydride may be symmetrical (two identical acyl groups) or mixed (two different acyl groups) to name, replace acid acid of the parent acid by anhydride anhydride COC OO 3 COCCH 3 Benzoic anhydride Acetic anhydride
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Acid Anhydrides Acid Anhydrides ± Cyclic anhydrides are named from the dicarboxylic acids from which they are derived Maleic anhydride O O O Phthalic anhydride Succinic anhydride O O O O O O Phosphoric Anhydrides Phosphoric Anhydrides ± A phosphoric anhydride contains two phosphoryl groups bonded to an oxygen atom ± Very important in biochemistry Esters ± The functional group of an ester is an acyl group bonded to -OR or -OAr name the alkyl or aryl group bonded to oxygen followed by the name of the acid change the suffix -ic ic acid to -ate ate O O Et O O OEt O O O Ethyl ethanoate (Ethyl acetate) Diethyl butanedioate (Diethyl succinate) Is op ropyl benzoate Esters Esters ± Cyclic esters are called lactones name the parent carboxylic acid, drop the suffix -ic ic acid and add –olactone olactone Location of the oxygen atom 4-Butanolactone -Butyrolactone) 3-Butanolactone -Butyrolactone) γ β α β α O O O O H 3 C 2 3 1 2 1 34 6-Hexanolactone -Caprolactone) ε δ γ β α O O 2 1 3 4 56 An anesthetic and addictive substance Anesthetic substances
Background image of page 2
A derivative of coumarin Esters of Phosphoric Acid phosphoric acid forms mono-, di-, and triesters name by giving the name of the alkyl or aryl group(s) bonded to oxygen followed by the word phosphate phosphate Esters of Phosphoric Acid Esters of Phosphoric Acid in more complex phosphoric esters, it is common to name the organic molecule and then indicate the presence of the phosphoric ester by the word phosphate or the prefix phospho phospho - OCH 3 CH 3 OPOH O C-H 2 -O-P-O - CHO HO O - O N HO H 3 C 2 O-P-O - O - O CO - C 2 OPO - O - O O Dimethyl phosphate Glyceraldehyde 3-phosphate Pyridoxal phosphate Phosphoenol- pyruvate Amides ±
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 09/06/2009 for the course CHEM chem 12 AB taught by Professor Valentin during the Spring '09 term at Evergreen Valley.

Page1 / 20

lecture 18 - Carboxyl Derivatives In this chapter, we study...

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online