Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 18.8, Problem 13P
Instead of adding to the 4a-position and protonating N-5, the thiolate ion could have added to the 10a-position and protonated N-1. Why is addition to the 4a-position favored? (Hint: Which nitrogen is a stronger base?)
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Which nitrogen-containing compound of each pair would you expect to be stronger base?Indicate (a) or (b)
Complete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right.
Predict the position of the equilibrium for the reaction and provide a brief explanation.
(The acidic protons are shown in red.)
86-08
O Reverse direction is favored because nitrogen is more electronegative, making B the weaker base and D the stronger acid.
O Forward direction is favored because nitrogen is more electronegative, making B the weaker base and D the stronger acid.
O Reverse direction is favored because carbon is less electronegative, making C the weaker base and A the stronger acid.
O Forward direction is favored because carbon is less electronegative, making C the weaker base and A the stronger acid.
Chapter 18 Solutions
Essential Organic Chemistry, Global Edition
Ch. 18.1 - Prob. 1PCh. 18.2 - If H218O were used to hydrolyze lysozyme, which...Ch. 18.3 - Which of the following amino acid side chains can...Ch. 18.3 - Arginine and lysine side chains fit into trypsins...Ch. 18.4 - Which of the following amino acid side chains can...Ch. 18.4 - Prob. 6PCh. 18.5 - Prob. 7PCh. 18.5 - Draw the mechanism for the hydroxide-ion-catalyzed...Ch. 18.5 - What advantage does the enzyme gain by forming an...Ch. 18.7 - Prob. 10P
Ch. 18.7 - Prob. 11PCh. 18.8 - How many conjugated double bonds are there in a....Ch. 18.8 - Instead of adding to the 4a-position and...Ch. 18.8 - In succinate dehydrogenase, FAD is covalently...Ch. 18.8 - Prob. 15PCh. 18.9 - Acetolactate synthase is another TPP-requiring...Ch. 18.9 - Acetolactate synthase can also transfer the acyl...Ch. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 21PCh. 18.11 - Prob. 23PCh. 18.11 - Which compound is more easily decarboxylated?Ch. 18.11 - Explain why the ability of PLP to catalyze an...Ch. 18.11 - Explain why the ability of PLP to catalyze an...Ch. 18.12 - What groups are interchanged in the following...Ch. 18.13 - Why is the coenzyme called tetrahydrofolate?Ch. 18.13 - What amino acid is formed by the following...Ch. 18.13 - How do the structures of tetrahydrofolate and...Ch. 18.13 - What is the source of the methyl group in...Ch. 18 - Prob. 32PCh. 18 - Prob. 33PCh. 18 - From what vitamins are the following coenzymes...Ch. 18 - Prob. 35PCh. 18 - For each of the following reaction, name both the...Ch. 18 - Explain why serine proteases do not catalyze...Ch. 18 - Prob. 38PCh. 18 - For each of the following enzyme catalyzed...Ch. 18 - Trisephosphate isomerase (TIM) catalyzes the...Ch. 18 - Prob. 41PCh. 18 - What acyl groups have we seen transferred by...Ch. 18 - When UMP is dissolved in T2O, exchange of T for H...Ch. 18 - Prob. 44PCh. 18 - When transaminated, the three branched-chain amino...Ch. 18 - Aldolase shows no activity if it is incubated with...
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- Rank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.arrow_forwardWhich is a stronger base: RO- or RS-?arrow_forwardIn each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.(a) (CH3)2NH + HCl ¡ (CH3)2 NH+2 + Cl-(b) (CH3)2NH + CH3Cl ¡ (CH3)3 NH++ Cl-arrow_forward
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