EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 9780100659469
Author: Bruice
Publisher: YUZU
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
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?)
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Q3: Describes the relationship (identical, constitutional isomers, enantiomers or diastereomers)
of each pair of compounds below.
ག
H
CH3
OH
OH
CH3
H3C
OH
OH
OH
//////////
C
CH3
CH3
CH3
CH3
H3C
CH 3
C/III.....
Physics & Astronomy
www.physics.northweste
COOH
H
нош.....
H
2
OH
HO
CH3
HOOC
H
CH3
CH3
CH3
Br.
H
H
Br
and
H
H
H
H
Q1: For each molecule, assign each stereocenter as R or S. Circle the meso compounds. Label
each compound as chiral or achiral.
OH
HO
CI
Br
H
CI
CI
Br
CI
CI
Xf x f g
Br
D
OH
Br
Br
H₂N
R.
IN
Ill
I
-N
S
OMe
D
II
H
CO₂H
1/111
DuckDuckG
These are synthesis questions. You need to show how the starting material can be converted into
the product(s) shown. You may use any reactions we have learned. Show all the reagents you
need. Show each molecule synthesized along the way and be sure to pay attention to the
regiochemistry and stereochemistry preferences for each reaction. If a racemic molecule is made
along the way, you need to draw both enantiomers and label the mixture as "racemic".
All of the carbon atoms of the products must come from the starting material!
?
H
H
Chapter 18 Solutions
EBK ESSENTIAL ORGANIC CHEMISTRY
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...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Q5: Draw every stereoisomer for 1-bromo-2-chloro-1,2-difluorocyclopentane. Clearly show stereochemistry by drawing the wedge-and-dashed bonds. Describe the relationship between each pair of the stereoisomers you have drawn.arrow_forwardClassify each pair of molecules according to whether or not they can participate in hydrogen bonding with one another. Participate in hydrogen bonding CH3COCH3 and CH3COCH2CH3 H2O and (CH3CH2)2CO CH3COCH3 and CH₂ CHO Answer Bank Do not participate in hydrogen bonding CH3CH2OH and HCHO CH3COCH2CH3 and CH3OHarrow_forwardNonearrow_forward
- Given the standard enthalpies of formation for the following substances, determine the reaction enthalpy for the following reaction. 4A (g) + 2B (g) → 2C (g) + 7D (g) AHrxn =?kJ Substance AH in kJ/mol A (g) - 20.42 B (g) + 32.18 C (g) - 72.51 D (g) - 17.87arrow_forwardDetermine ASran for Zn(s) + 2HCl(aq) = ZnCl2(aq) + H2(aq) given the following information: Standard Entropy Values of Various Substance Substance So (J/mol • K) 60.9 Zn(s) HCl(aq) 56.5 130.58 H2(g) Zn2+(aq) -106.5 55.10 CI (aq)arrow_forward3) Catalytic hydrogenation of the compound below produced the expected product. However, a byproduct with molecular formula C10H12O is also formed in small quantities. What is the by product?arrow_forward
- What is the ΔHorxn of the reaction? NaOH(aq) + HCl(aq) → H2O(l) + NaCl(aq) ΔHorxn 1= ________ kJ/molarrow_forward= +92kJ ΔΗ = +170kJ Use the following reactions: 2NH3(9) N2(g) + 3H2(g) → 11/N2(g) + 2H2O (1) → NO2(g) + 2H2(g) Determine the DH° of this reaction: NO2(g) + H2(g) → 2(g) → 2H2O(l) + NH3(9) ΔΗarrow_forwardDetermine the entropy change for the reaction SO2(g) + O2(g) following information: Standard Entropy Values of Various Substance Substance SO2(g) 02(g) SO3(g) So (J/mol K) 248.2 205.0 256.8 → SO3(g) given thearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY