Complete the mechanism of the given enamine to imine tautomerization by adding any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Then, indicate which of the species will predominate at equilibrium. NH-R is a generic acid with conjugate base :NH,-R in solution. Note the resonance arrows in the scheme. Step 1: add curved arrows. Step 2: complete the structure and add curved arrows. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase H C H H,N -R H,N - R H H. H. H 1L

Complete the mechanism of the given enamine to imine tautomerization by adding any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Then, indicate which of the species will predominate at equilibrium. NH-R is a generic acid with conjugate base :NH,-R in solution. Note the resonance arrows in the scheme. Step 1: add curved arrows. Step 2: complete the structure and add curved arrows. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase H C H H,N -R H,N - R H H. H. H 1L

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter23: Addition To A Carbonyl

Section: Chapter Questions

Problem 24E

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Complete the mechanism of the given enamine to imine tautomerization by adding any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Then, indicate which of the species will predominate at equilibrium. NH -R is a generic acid with conjugate base :NH, -R in solution. Note the resonance arrows in the scheme. Step 1: add curved arrows. Step 2: complete the structure and add curved arrows. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase с | н N H N H,N - R H,N H H
The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and whether there is a second carbonyl group attached to the a-carbon. Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is indicated in blue in each structure. Highest acidity Lowest acidity Answer Bank H CH3 H CH3 H. CH3 H3C CH3 H3C CH3 H. H. H3C. CH3 H. H 0-CH3
Can you select the answers in each bracket? The imine functionality is similar to [ carbonyl / nucleophile / acid / amine] meaning that it can react as [ electrophile / nucleophile / proton acceptor / proton donor ] if paired with [ electrophile / nucleophile / acid / base ] . Similarly to, [ carbonyls / enols / alkenes/ bases ], enamines will undergo alpha substitutions when paired with [ electrophile / nucleophile / acid / base ] .
Complete the mechanism of the given acid-catalyzed imine to enamine tautomerization by adding any missing atoms bonds, charges, nonbonding electrons, and curved arrows. NH-R is a generic acid with conjugate base :NH, -R in solution. Then, indicate which tautomer predominates at equilibrium. Step 2: complete the structure and add curved arrows. Step 1: imine: add curved arrows. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase Create Groups C H,N - H,N -R H. 1L
The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and whether there is a second carbonyl group attached to the a-carbon. Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is indicated in blue in each structure. Highest acidity Lowest acidity Answer Bank H;C, CH, H- CH, CH H3C CH3 H H. CH3 H3C H. CH3 CH3 H
The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and whether there is a second carbonyl group attached to the a-carbon. Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is indicated in blue in each structure. Highest acidity Lowest acidity Answer Bank H. H. CH3 H. -CH CH3 H.C H. H3C CH3 H. H. CH H. H,C CH3 H. H. H. -CH
Step 3: The mechanism of the protonation is pre-drawn for you. Step 4: Omit H,0. Complete the structure and draw curved arrows. :0 :0: H. :0: 4- 0: Step 5: H,O is included here for use in the final step. Draw curved arrows. Step 6: Complete the final products. :0 : :0: H.
Complete the mechanism for the given enamine reaction by drawing curved arrows, atoms, bonds, charges, and nonbonding electrons where indicated. Step 1: Add curved arrows for this carbon bond formation. Select Draw Rings More C Select H Br N Step 3: Draw the hydrolyzed products. C Erase Draw H N 0 Step 2: The iminium intermediate is drawn for you. iminium Rings :Br: More +H₂O -HBr
Amides are weak nucleophiles but their conjugate bases are string nucleophiles. The amide drawn below can be deprotonated in four possible locations, labeled A-D but two are considerably more acidic than the others. Draw the two different Bronsted Lowery acid/base reactions (using HO- as the BL base) showing the deprotonation at these two locations. Draw all RS with arrows for both conjugate bases but no hybrids. Based on your resonance analysis which location is the most acidic in the molecule? Why is it most acidic? Amides can also be protonated by a strong acid in two different locations. Draw two different conjugate acids for the amide above as well as RS with arrows for each. Based on your resonance analysis which atom is the most basic in an amide?
Using the reaction shown in Box (the attack of an amine on the carbonyl group of a ketone) as a starting point, draw curved arrows to represent the base-catalyzed reaction (when the group —B: is present).
Click the "draw structure" button to launch the drawing utility. Report problem Draw the product of the following reaction by following the curved arrows. Hint HÖ: :ÖH Solution Guided Solution Gö-H draw structure .
Copy the given reaction and show the mechanism by supplying the appropriate curved arrows. Also, identify the general type of reaction mechanism (polar or non-polar). For polar reaction mechanisms, label the nucleophile and the electrophile. :0: :0 O.. H. HÖ: Hö: