OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305671874
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 27.SE, Problem 45AP
Propose a synthesis of diethylstilbestrol (Problem 27-44) from phenol and any other organic compound required.
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Q4: Rank the relative nucleophilicity of halide ions in water solution and DMF solution,
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F CI
Br |
Q5: Determine which of the substrates will and will not react with NaSCH3 in an SN2 reaction to
have a reasonable yield of product.
NH2
Br
Br
Br
OH
Br
Q7: Rank the following groups in order of basicity, nucleophilicity, and leaving group ability.
a) H₂O, OH, CH3COOT
b) NH3, H₂O, H₂S
Q8: Rank the following compounds in order of increasing reactivity in a nucleophilic substitution
reaction with CN as the nucleophile.
Br
A
B
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LL
F
C
D
OH
CI
LLI
E
Q9: Complete the missing entities for following reactions (e.g., major product(s), reactants,
and/or solvents) for the SN2 reactions to occur efficiently. Include curved-arrow mechanism for
reactions a) to d).
a)
H
"Cl
D
+
-OCH 3
Page 3 of 5
Chapter 27 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
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- Q10: (a) Propose a synthesis of C from A. (b) Propose a synthesis of C from B. Br Br ...\SCH 3 A B Carrow_forward9: Complete the missing entities for following reactions (e.g., major product(s), reactants, and/or solvents) for the SN2 reactions to occur efficiently. Include curved-arrow mechanism for reactions a) to d).arrow_forwardComplete the missing entities for following reactions (e.g., major product(s), reactants, and/or solvents) for the SN2 reactions to occur efficiently. Include curved-arrow mechanism for reactions a) to d).arrow_forward
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