I. Glucose: Finding the Hemiacetal CarbonII. Equilibrium Differences in Inter vs. Intra-molecular Hemiacetal ReactionsIII. You cannot make a full acetal under acidic conditionsIV. Acetal Protecting GroupsI. Keto and Primary AmineII. Iminium Ion IntermediateIII. To Hydrolyze Imine Back to Keto FormIV. Keto and Secondary AmineI. Keto and Primary Amine (i.e. methylamine for this example)a. Ketone + primary amine acid catalyst  imine + waterb. This is done via the formation of the iminium ion intermediatec. Mechanism:i. Ketone oxygen attacks H of protonated methylamine: protonation of the ketone oxygenii. Lone pair of electrons on the Nitrogen of NH2CH3 (methylamine) attack partial positive carbonyl carbon, kicking out electrons onto the ketone oxygeniii. N has a positive charge, it is bonded to 4 things: carbonyl C, and its two H and methyl group. The next step is to get rid of OH.iv. The OH oxygen attacks H from the attached NH2CH3 group, electrons get kicked back onto Nitrogen. You form water, which is a good leaving groupv. Water leaves, and electrons from Nitrogen form a pi bond.1. You have formed your iminium ion intermediatevi. Deprotonation of the iminium ion intermediate follows: oxygen from water removes H from iminium ion, regenerating your acid catalyst, and imine product.1. Imine contains a carbon nitrogen double bond. That nitrogen is also attached to H or R groups.II. Iminium Ion Intermediatea. The iminium ion intermediate is just a protonated imine (the structure of the imine is described above)III. To Hydrolyze Imine Back to Keto Forma. Stir in aqueous solution and acidb. Propose your own mechanism and check it in the packet that is provided to you on Course Web.IV. Keto and Secondary Amine (you are responsible for both forward and reverse)a. There is no neutral imine hereb. Ketone + secondary amine in catalytic acid  enamine + regenerated catalyst (only the forward reaction is described below)i. Protonate the ketone using the protonated secondary amine (catalyst)ii. Nucleophilic attack of the lone pairs on the N on the carbonyl Ciii. Make OH leave by turning it into a good leaving group1. Intramolecular protonation, and then lone pairs from N form pi bond, kicking off wateriv. Make you enamine using E21. You have regenerated your catalyst in the process.CHEM 0320 1nd Edition Lecture 19Outline of Last Lecture I. Glucose: Finding the Hemiacetal Carbon II. Equilibrium Differences in Inter vs. Intra-molecular Hemiacetal Reactions III. You cannot make a full acetal under acidic conditionsIV. Acetal Protecting Groups Outline of Current Lecture I. Keto and Primary Amine II. Iminium Ion Intermediate III. To Hydrolyze Imine Back to Keto FormIV. Keto and Secondary Amine Current Lecture: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. Keto and Primary Amine (i.e. methylamine for this example)a. Ketone + primary amine acid catalyst  imine + waterb. This is done via the formation of the iminium ion intermediate c. Mechanism: i. Ketone oxygen attacks H of protonated methylamine: protonation of the ketone oxygenii. Lone pair of electrons on the Nitrogen of NH2CH3 (methylamine) attack partial positive carbonyl carbon, kicking out electrons onto the ketone oxygen iii. N has a positive charge, it is bonded to 4 things: carbonyl C, and its two H and methyl group. The next step is to get rid of OH. iv. The OH oxygen attacks H from the attached NH2CH3 group, electrons get kicked back onto Nitrogen. You form water, which is a good leaving groupv. Water leaves, and electrons from Nitrogen form a pi bond. 1. You have formed your iminium ion intermediate vi. Deprotonation of the iminium ion intermediate follows: oxygen from water removes H from iminium ion, regenerating your acid catalyst, and imine product.1. Imine contains a carbon nitrogen double bond. That nitrogen is also attached to H or R groups.II. Iminium Ion Intermediate a. The iminium ion intermediate is just a protonated imine (the structure of the imine is described above)III. To Hydrolyze Imine Back to Keto Forma. Stir in aqueous solution and acid b. Propose your own mechanism and check it in the packet that is provided to you on Course Web.IV. Keto and Secondary Amine (you are responsible for both forward and reverse)a. There is no neutral imine hereb. Ketone + secondary amine in catalytic acid  enamine + regenerated catalyst (only the forward reaction is described below)i. Protonate the ketone using the protonated secondary amine (catalyst) ii. Nucleophilic attack of the lone pairs on the N on the carbonyl C iii. Make OH leave by turning it into a good leaving group 1. Intramolecular protonation, and then lone pairs from N form pi bond, kicking off water iv. Make you enamine using E21. You have regenerated your catalyst in the