Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 8.4, Problem 13P
Arrange the following
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10.
Stereochemistry. Assign R/S stereochemistry for the chiral center indicated on the
following compound. In order to recieve full credit, you MUST SHOW YOUR WORK!
H₂N
CI
OH
CI
カー
11. () Stereochemistry. Draw all possible stereoisomers of the following compound. Assign
R/S configurations for all stereoisomers and indicate the relationship between each as
enantiomer, diastereomer, or meso.
NH2
H
HNH,
-18
b)
8.
Indicate whether the following carbocation rearrangements are likely to occur
Please explain your rational using 10 words or less
not likely to occur
• The double bond is still in the
Same position
+
Likely
to oc
occur
WHY?
-3
H3C
Brave
Chair Conformers. Draw the chair conformer of the following substituted
cyclohexane. Peform a RING FLIP and indicate the most stable
conformation and briefly explain why using 20 words or less.
CI
2
-cobs ??
MUST INDICATE H -2
-2
Br
EQ
Cl
OR
AT
Br
H&
most stable
WHY?
- 4
CH
12
Conformational Analysis. Draw all 6 conformers (one above each letter) of the
compound below looking down the indicated bond. Write the letter of the
conformer with the HIGHEST and LOWEST in energies on the lines provided.
NOTE: Conformer A MUST be the specific conformer of the structure as drawn below
-4 NOT
HOH
OH
3
Conformer A:
Br
OH
A
Samo
Br H
04
Br
H
H3
CH₂
H
anti
stagere
Br CH
clipsed
H
Brott
H
IV
H
MISSING 2
-2
B
C
D
E
F
X
6
Conformer with HIGHEST ENERGY:
13. (1
structure
LOWEST ENERGY:
Nomenclature. a) Give the systematic (IUPAC) name structure. b) Draw the
corresponding to this name. HINT: Do not forget to indicate stereochemistry
when applicable.
a)
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2
"Br
{t༐B,gt)-bemn€-nehpརི་ཚ༐lnoa
Parent name (noname)
4 Bromo
Sub = 2-methylethyl-4 Bromo nonane
b) (3R,4S)-3-chloro-4-ethyl-2,7-dimethyloctane
# -2
-2
Chapter 8 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 8.1 - Prob. 2PCh. 8.1 - Does increasing the energy barrier for an SN2...Ch. 8.1 - Arrange the following alkyl bromides in order from...Ch. 8.2 - Prob. 7PCh. 8.2 - Which reaction in each of the following pairs...Ch. 8.2 - Prob. 9PCh. 8.2 - Prob. 11PCh. 8.3 - Draw the substitution products that will be formed...Ch. 8.4 - Arrange the following alkyl halides in order from...Ch. 8.5 - Prob. 14P
Ch. 8.5 - Which of the following reactions will go faster if...Ch. 8.6 - After a proton is removed from the OH group, which...Ch. 8.6 - Draw the product of each of the following...Ch. 8.9 - Prob. 20PCh. 8.9 - Prob. 21PCh. 8.11 - Why do the SN1/E1 reactions of tertiary alkyl...Ch. 8.11 - Prob. 23PCh. 8.11 - Prob. 24PCh. 8.12 - Prob. 25PCh. 8.12 - Prob. 26PCh. 8.12 - Prob. 27PCh. 8.12 - a In which solvent would tert-butyl bromide...Ch. 8.13 - What would be the best way to prepare the...Ch. 8 - Methoxychlor is an insecticide that was intended...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Explain how the following changes would affect the...Ch. 8 - Prob. 38PCh. 8 - Draw the major product obtained when each of the...Ch. 8 - Which alkyl halide in Problem 39 can undergo an El...Ch. 8 - Prob. 42PCh. 8 - Prob. 43PCh. 8 - Prob. 44PCh. 8 - Prob. 45PCh. 8 - Starting with bromocyclohexane, how could the...Ch. 8 - Prob. 48PCh. 8 - Fill in the blanks in the following chemical...Ch. 8 - For each of the following alkyl halides, indicate...Ch. 8 - Prob. 51PCh. 8 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 8 - An ether can be prepared by an SN2 reaction of an...Ch. 8 - Give two sets of reactants (each set including an...Ch. 8 - Show how the following compounds could be...Ch. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Draw the structures of the products obtained from...Ch. 8 - cis-4-Bromocyclohexanol and...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - In which solventethanol or diethyl etherwould the...Ch. 8 - The pKa of acetic acid in water is 4.76. What...
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