Interpretation:
In a Gabriel synthesis, the yield of the
Concept introduction:
In the Gabriel synthesis, phthalimide is first treated with a strong base such as potassium hydroxide, followed by an
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- Identify the electrophile and the nucleophile in each of the following reaction steps. Then draw curved arrows to illustrate the bond-making and bond-breaking processes.arrow_forwardComplete the mechanism for these Lewis acid-base reactions. Draw mechanistic arrows and partial charges where appropriate. Reaction A: CH₂NH₂ + HCl = 3 Reaction B: CH₂NH₂ + H₂O = 3 Reaction C: CH₂NH¯ + H₂O = 3 + Reaction D: CH₂NH 3 + H₂O 2 When each of these reactions has come to an equilibrium (where the relative amounts of each chemical species remains unchanged but the forward and reverse reactions are still occurring), predict whether each reaction will have more reactant or more product. Explain your predictions using your knowledge of atomic and molecular structures and electronegativity.arrow_forwardComplete the mechanism below with the missing structure and arrows. Also identify any acids, bases, electrophiles and nucleophiles. =NEN- -서 -N는N Product(s)arrow_forward
- 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-CH3arrow_forwardThe 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 Harrow_forwardThe bromination of benzene requires a Lewis acid catalyst such as FeBr3, butthe bromination of naphthalene does not. Explain why.arrow_forward
- Help. Please order these compounds from the fastest rate of acid-catalyzed hydrolysis to give acetic acid, to the slowest.arrow_forwardThe 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. -CHarrow_forwardSelect the best reagent to complete the job. You may assume a separate protonation step where relevant.arrow_forward
- Complete the following reaction with its mechanism.arrow_forwardAmides 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?arrow_forwardComplete the reaction wheels below. For the starred reactions, draw the full reaction mechanism. Once complete, compare and contrast the common reactions shared by acyl halides and acid anhydrides.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning