318-11 - CH 318 N Textbook Assignment: Chapter 16 Homework...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
CH 318 N LECTURE 11 Textbook Assignment: Chapter 16 Homework (for credit): POW 6 posted Today’s Topics: Additions; Wittig and related reactions Notice & Announcements: Exam 1-Wednesday, 2/25 7-9 PM WEL 3.502 Organic Lecture Series 2 Aldehydes Aldehydes And And Ketones Ketones
Background image of page 1

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

View Full DocumentRight Arrow Icon
Organic Lecture Series 3 Drawing Mechanisms Drawing Mechanisms Use double-barbed arrows to indicate the flow of pairs of e - Draw the arrow from higher e - density to lower e - density i.e. from the nucleophile to the electrophile Removing e - density from an atom will create a formal + charge Adding e - density to an atom will create a formal - charge Proton transfer is fast (kinetics) and usually reversible Organic Lecture Series 4 Organolithium compounds are generally more reactive in C=O addition reactions than RMgX, and typically give higher yields Li O O - + HCl H 2 O OH 3,3-Dimethyl-2- butanone 3,3-Dimethyl-2-phenyl- 2-butanol (racemic) + Phenyl- lithium A lithium alkoxide (racemic) Organolithium Organolithium Reagents Reagents
Background image of page 2
Organic Lecture Series 5 • Addition of an alkyne anion followed by H 3 O + gives an α -acetylenic alcohol • Note: this is a 2-C homologation C: - Na + HC O CO - + HCl H 2 O C OH 1-Ethynyl- cyclohexanol A sodium alkoxide + Cyclohexanone Sodium acetylide Salts of Terminal Alkynes Salts of Terminal Alkynes Homologation is a term used for extending a carbon chain Organic Lecture Series 6 Oxidation of Terminal Alkynes Oxidation of Terminal Alkynes Chapter 7: use of (sia) 2 BH H 2 O HO C CH H 2 SO 4 ,HgSO 4 1. (sia) 2 BH 2. H 2 O 2 ,NaOH 2 O An α -hydroxyketone A β -hydroxyaldehyde α β O CCH 3 α
Background image of page 3

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

View Full DocumentRight Arrow Icon
Organic Lecture Series 7 • HCN adds to the C=O group of an aldehyde or ketone to give a cyanohydrin • Cyanohydrin: Cyanohydrin: a molecule containing an - OH group and a -CN group bonded to the same carbon Addition of HCN Addition of HCN H 3 C C O H + HCN H 3 C C HO H C N 2-Hydroxypropanenitrile (Acetaldehyde cyanohydrin) Acetaldehyde Organic Lecture Series 8 • Mechanism of cyanohydrin formation
Background image of page 4
Image of page 5
This is the end of the preview. Sign up to access the rest of the document.

Page1 / 13

318-11 - CH 318 N Textbook Assignment: Chapter 16 Homework...

This preview shows document pages 1 - 5. Sign up to view the full document.

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