Chapter 18-3

Chapter 18-3 - CHEM 262 Wei You Chapter 18 Functional...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
CHEM 262 Wei You Chapter 18. Functional Derivatives of Carboxylic Acids (3)
Background image of page 1

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

View Full DocumentRight Arrow Icon
Rxn with Grignard Reagents treating a formic ester with 2 moles of Grignard reagent followed by hydrolysis in aqueous acid gives a 2° alcohol treating other esters with 2 moles of Grignard reagent followed by hydrolysis in aqueous acid gives a 3° alcohol OCH 3 O 2 RMgX H 2 O ,  HC l HC - R C 3 O + magnesi u m       al koxi de         sa lt + C 3 3 O 2 RMgX 2 O ,  HC l C 3 - R R O H 3 H magnesi u m       a l k ox i de         sa lt + +
Background image of page 2
Reaction with Grignard Reagents 1. addition of 1 mole of RMgX to the carbonyl carbon gives a TCAI 1. collapse of the TCAI gives a ketone (an aldehyde from a formic ester) O CH 3 -C-OCH 3 R MgX O R OCH 3 CH 3 -C [MgX] + CH 3 -C R O CH 3 - [ MgX] + 1 1 + - + A magnesium salt (a tetrahedral carbonyl addition intermediate) A ketone 2 2
Background image of page 3

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

View Full DocumentRight Arrow Icon
Reaction with Grignard Reagents 3. reaction of the ketone with a 2nd mole of RMgX gives a second TCAI 4. treatment with aqueous acid gives the alcohol CH 3 -C O R R MgX CH 3 -C-R R [MgX] + H 2 O, HCl CH 3 -C-R R OH Magnesium salt A ketone + A 3° alcohol 3 3 (4)
Background image of page 4
Rxns with RLi Organolithium compounds are even more powerful
Background image of page 5

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

View Full DocumentRight Arrow Icon
Image of page 6
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 06/12/2010 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

Page1 / 17

Chapter 18-3 - CHEM 262 Wei You Chapter 18 Functional...

This preview shows document pages 1 - 6. Sign up to view the full document.

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