EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
3rd Edition
ISBN: 9780133858501
Author: Bruice
Publisher: PEARSON CO
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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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In each reaction, Label the reactants as a Lewis base (nucleophile) or a Lewis acid
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NH,
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Which nitrogen-containing compound of each pair would you expect to be stronger base?Indicate (a) or (b)
Draw the major organic oduct of the Bronsted acid-base reaction.
Include all lone pairs and charges as appropriate. Ignore any counterions.
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Chapter 18 Solutions
EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
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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- Complete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right.arrow_forwardPredict 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.arrow_forwardRank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.arrow_forward
- List the following organic bases in order of increasing basicity, starting with the least basic one and ending with the most basic one. Please just write down the letters! Please don't use notation, just use commas between the letters! CH3 A NaOH B CH3 C CH3 N D Jarrow_forwardWhich is a stronger base: RO- or RS-?arrow_forwardIndicate which is the weaker base and explain why. Be specific! NH3 or NF3arrow_forward
- In 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_forwardhydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone. CH,ČCH, H CH,CH, H Acetone Ethane pK, 20.2 pK, 51arrow_forwardComplete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right.arrow_forward
- For the following acid-base reaction, predict the position of the equilibrium and identify the most stable base. + NaOH || A. favor the right side with compound I being the most stable base B. favor the right side with compound II being the most stable base OC. favor the right side with compound III being the most stable base OD. favor the left side with compound I being the most stable base E. favor the left side with compound II being the most stable base سمیر ||| + H₂O IVarrow_forwardRank the labeled protons (Ha~He) in order of increasing acidityarrow_forwardWhich is a stronger base? CH3 CHCO F CH3 CHCO- Brarrow_forward
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