I. Keto and Primary AmineII. Iminium Ion IntermediateIII. To Hydrolyze Imine Back to Keto FormIV. Keto and Secondary AmineI. Deoxygenation of Aldehydes and KetonesII. Wolff KishnerIII. Wittig ReactionI. Deoxygenation of Aldehydes and Ketonesa. No mechanism is required for these reactionsb. Note acidic reaction conditionsII. Wolff Kishnera. Ketone + NH2NH2 (hydrazine) + NaOH + heat  alkanei. Mechanism:1. OH attacks H, deprotonates the hydrazone making its ion form and water2. The ion formed is resonance stabilized. The resonance form, where there is a carbanion, attacks water and deprotonates the water.3. OH attacks and deprotonates the H on the N-H bond, kicking the electrons to the double bond N-N, making a triple bond N-N, which leaves. Carbanion forms.4. Protonate the carbanion using water, reforming base and forming the alkane.III. Wittig Reactiona. Overall: Me, primary, or secondary alkyl halide + PPh3, nBuLi, aldehyde/ketone  carbonyli. P in PPh3 is a good nucleophile. The Phare 3 phenyl groups. It is not sterically hindered as much because it is still a great nucleophileii. nBuLi is a strong baseiii. alkyl halide carbon becomes carbonyl carbon in the productiv. Mechanism:1. SN2: P of PPh3 attacks the partial positive carbon of the alkyl halide, and replacing the halide.2. Strong base de-protonates Hydrogen, forming a pi bond with the PPh3a. The synthetic intermediate formed is called an ylide.b. The octet is violated here, but it is possible because P is a period 3 element3. Wittig: The pi electrons from the newly formed pi bond form a carbanion. That lone pair of electrons attack the carbonyl carbon of a given ketone/aldehyde, forming a new C- C bond while kicking off the electrons from the carbonyl bond back onto the oxygen.4. The negatively charged oxygen attacks the positively charged P. forming a temporary ring system5. The ring system collapses, sigma electrons become pi electrons around 2 axes.a. Ph3P = O and carbonyl are the two productsb. The driving force is the Ph3P = O (P double bonded to O, which is a very strong bond)6. This is a powerful reaction for alkene synthesisCHEM 0320 1st Edition Lecture 20Outline of Last Lecture I. Keto and Primary Amine II. Iminium Ion Intermediate III. To Hydrolyze Imine Back to Keto FormIV. Keto and Secondary Amine Outline of Current Lecture I. Deoxygenation of Aldehydes and Ketones II. Wolff Kishner III. Wittig ReactionCurrent Lecture:I. Deoxygenation of Aldehydes and Ketones a. No mechanism is required for these reactions b. Note acidic reaction conditions II. Wolff Kishner a. Ketone + NH2NH2 (hydrazine) + NaOH + heat  alkane i. Mechanism:1. OH attacks H, deprotonates the hydrazone making its ion form andwater2. The ion formed is resonance stabilized. The resonance form, where there is a carbanion, attacks water and deprotonates the water. 3. OH attacks and deprotonates the H on the N-H bond, kicking the electrons to the double bond N-N, making a triple bond N-N, which leaves. Carbanion forms.4. Protonate the carbanion using water, reforming base and forming the alkane.III. Wittig Reactiona. Overall: Me, primary, or secondary alkyl halide + PPh3, nBuLi, aldehyde/ketone carbonyl These notes represent a detailed interpretation of the professor’s lecture. GradeBuddy is best used as a supplement to your own notes, not as a substitute.i. P in PPh3 is a good nucleophile. The Phare 3 phenyl groups. It is not sterically hindered as much because it is still a great nucleophileii. nBuLi is a strong base iii. alkyl halide carbon becomes carbonyl carbon in the product iv. Mechanism: 1. SN2: P of PPh3 attacks the partial positive carbon of the alkyl halide, and replacing the halide. 2. Strong base de-protonates Hydrogen, forming a pi bond with the PPh3a. The synthetic intermediate formed is called an ylide.b. The octet is violated here, but it is possible because P is a period 3 element3. Wittig: The pi electrons from the newly formed pi bond form a carbanion. That lone pair of electrons attack the carbonyl carbon of a given ketone/aldehyde, forming a new C- C bond while kickingoff the electrons from the carbonyl bond back onto the oxygen. 4. The negatively charged oxygen attacks the positively charged P. forming a temporary ring system5. The ring system collapses, sigma electrons become pi electrons around 2 axes. a. Ph3P = O and carbonyl are the two productsb. The driving force is the Ph3P = O (P double bonded to O, which is a very strong bond)6. This is a powerful reaction for alkene