Organic Chemisty II
Organic Chemisty II CHEM 2320
Utah State University
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This 30 page Class Notes was uploaded by Ansel Ankunding PhD on Wednesday October 28, 2015. The Class Notes belongs to CHEM 2320 at Utah State University taught by Staff in Fall. Since its upload, it has received 15 views. For similar materials see /class/230509/chem-2320-utah-state-university in Chemistry and Biochemistry at Utah State University.
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Date Created: 10/28/15
Chapter 18 Carbonyl Compounds 11 Learning Objectives 1 Recognize and assign names to aldehydes and ketones 2 Write the mechanism for nucleophilic addition and nucleophilic additionelimination reactions of aldehydes and ketones and be able to predict the products of such reactions 3 Be able to explain the relative reactivity of carbonyl compounds toward nucleophilic addition 4 Be able to describe the concept of employing protecting groups 5 Predict the products of the reactions of carbonyl compounds with Grignard reagents hydride ion donors sulfur nucleophiles and with phosphonium ylides the Wittig reaction 6 Be able to recognize Re and Si faces of carbonyl compounds and the stereochemistry outcomes from a nucleophilic addition 7 Predict the products of addition reactions to 0cBunsaturated carbonyl compounds Sections 18 1 Nomenclature 182 Relative Reactivities of Carbonyl Compounds 183 How Aldehydes and Ketones React 184 Reaction of Carbonyl Compounds with Carbon Nucleophiles 185 Reaction of Carbonyl Compounds with Hydride Ion 186 Reaction of Aldehydes and Ketones with Nitrogen Nucleophiles 187 Reaction of Aldehydes and Ketones with Oxygen Nucleophiles 188 Protecting Groups 189 Addition of Sulfur Nucleophiles 1810 The Wittig Reaction 1811 Stereochemistry of Nucleophilic Addition Reactions Re and Si Faces f 1812 Designing a Synthesis V Disconnections Synthones and Synthetic Equivalents 1813 Nucleophilic Addition to 0cBUnsaturated Aldehydes and Ketones 1814 Nucleophilic Addition to 0cBUnsaturated Carboxylic Acid Derivatives 1815 Enzymecatalyzed Additions to 0cBUnsaturated Carbonyl Compounds Sections that will be focused Sections that will be skipped Recommended additional problems 840 7 855 858 7 861 863 7 867 869 7 872 874 Class Note 18 1 Nomenclature A Oi 1H 01H 0 H H HO 0 M H M O 0 ml H g HMOCHZCW Mocmcm o 0 CH0 0 18 2 Nucleoph ic addition 183 How Aldehydes and Ketones React A In basic condition o39 6 9 Nu 2 Relative Reactivities of Carbonyl Compounds 639 o 390 Nu H Si R HR R HR tetrahedral intermediate B In acidic condition H B B H ea 39O39 39o H H o39 3 H R RXH R R HR 184 Reaction of Carbonyl Compounds with Carbon Nucleophiles A Carbon nucleophile basic or acidic B Reaction of aldehydes and ketones with Grignard reagent C Reactions of ester and carboxylic acid with Grignard reagent D Reactions of aldehydes and ketones with acetylide ions i pKa of H R CHCH H R CC H R CH2 CH2 ii Mechanism E Reactions of aldehydes and ketones with hydrogen cyanide i pKa of HCN ii Mechanism iii Synthesis of xhydroxy carboxylic acid 185 Reaction of Carbonyl Compounds with Hydride Ion A Source of hydride B Reduction of aldehydes and ketones C Reduction of esters D Reduction of carboxylic acids E Reduction of amides 186 Reaction of Aldehydes and Ketones with Nitrogen Nucleophiles A pKa of amines B Addition of primary amines C Addition of secondary amines D Addition of hydrazine hydroxyamine E Mechanism of WolffKishner reduction Reaction of Aldehydes and Ketones with Oxygen Nucleophiles 18 7 A Addition of water formation of hydrate gemdiol geminal diol o39 i HO i Consideration of pKa ii Stability consideration B Addition of alcohol formation of hemiacetal acetal hemiketal and ketal o39 R39O 9H R H R H HOR39 2 equivalents o39 i R39O 9H R R 1 R R HOR39 2 equivalents R H H 20 R R H 20 C Mechanism 18 8 Protecting Groups A Stability of acetals and ketals B Example HOCHZCHZOH i OCH3 gt gt 20 O O O OH C More examples 0 NH2 NHz gt gt gt N02 ii NH2 NH2 gt gt gt cogH 21 189 Addition of Sulfur Nucleophiles 1810 The Wittig Reaction A Wittig reagents 9 en C6H53P CH2 lt gt CeH53P CH2 phosphonium ylide B Formation of Wittig reagents 22 C Reactions i Synthesis of ii Synthesis of O 23 D StereoselectiVity E VS Z E Arbuzov Perkow reaction and HornerEmmons reaction i HornerEmmons reaction 24 ii Arbuzov Perkow reaction 25 1812 Designing a Synthesis V Disconnections Synthones and Synthetic Equivalents A Retrosynthetic analysis Example IIIOH OH synthesis of from 26 1813 Nucleophilic Addition to 0cBUnsaturated Aldehydes and Ketones A Analysis of 0cBunsaturated aldehydes and ketones o VkR 4 X B Direct addition 12addition and conjugate addition 14 addition 27 C Examples 0 O G 1 c 2 HCI ii HSCH3 gt iii 28 iV 1 NaBH4 CeCI3 2 20 14 gt V O 1 CHgMgBr i 2 H20 H gt H Vi 1 CH3MgBr 2 H20 14 gt 29 Vii 1 CH32CULi 2 H20 H gt 1814 Nucleophilic Addition to 0cBUnsaturated Carboxylic Acid Derivatives 0 CI HOCH3 gt o NHCH 3 HOCH3 O 1 LiAIH4 2 H20 W gt OCH3 O NH3 excess gt lCI 30
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