ORGANIC CHEMISTRY BOOK& SG/SM
6th Edition
ISBN: 9781264094493
Author: SMITH
Publisher: MCG
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Chapter 9, Problem 44P
What
a. 
b. 
c. 
d. 
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Q4: Rank the relative nucleophilicity of halide ions in water solution and DMF solution,
respectively.
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
NH2
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 9 Solutions
ORGANIC CHEMISTRY BOOK& SG/SM
Ch. 9.1 - Problem 9.1 Label each ether and alcohol in...Ch. 9.3 - Give the IUPAC name for each compound.Ch. 9.3 - Problem 9.3 Give the structure corresponding to...Ch. 9.3 - Name each of the following ethers.Ch. 9.3 - Name each epoxide.
a. (two ways) b. c. (two...Ch. 9.6 - Problem 9.8 Draw the organic product of each...Ch. 9.6 - Prob. 9PCh. 9.6 - Problem 9.10 Draw the products of each reaction.
...Ch. 9.8 - Problem 9.11 Draw the products formed when each...Ch. 9.8 - Prob. 12P
Ch. 9.11 - Problem 9.18 Draw the products of each reaction,...Ch. 9.11 - Problem 9.19 What is the major product formed...Ch. 9.12 - Prob. 19PCh. 9.12 - Prob. 20PCh. 9.12 - Problem 9.22 Draw the organic products formed in...Ch. 9.12 - Problem 9.23 Draw two steps to convert into each...Ch. 9.13 - Prob. 23PCh. 9.13 - Problem 9.25 Draw the products of each reaction,...Ch. 9.13 - Draw the products formed when (S)-butan-2-ol is...Ch. 9.13 - Draw the product formed when (CH3)2CHOH is treated...Ch. 9.14 - What alkyl halides are formed when each ether is...Ch. 9.14 - Explain why the treatment of anisole with HBr...Ch. 9.15 - Name each thiol.
a. b.
Ch. 9.15 - Draw the product of each reaction. ac b.d.Ch. 9.15 - Give the IUPAC name for each sulfide.
a. b.
Ch. 9.15 - Draw the product of each reaction.
a. b.
Ch. 9.16 - Prob. 33PCh. 9.16 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9.16 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 38PCh. 9 - 9.40 Give IUPAC name for each...Ch. 9 - Prob. 40PCh. 9 - Prob. 41PCh. 9 - 9.46 What alkenes are formed when each alcohol is...Ch. 9 - Prob. 46PCh. 9 - Prob. 51PCh. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 53PCh. 9 - 9.59 Draw two different routes to each of the...Ch. 9 - Prob. 55PCh. 9 -
9.61 Draw the products formed when each ether is...Ch. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 59PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - Prob. 64PCh. 9 - Prob. 75P
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Nomenclature: Crash Course Chemistry #44; Author: CrashCourse;https://www.youtube.com/watch?v=U7wavimfNFE;License: Standard YouTube License, CC-BY