Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 7, Problem 49P
What stereoisomers are obtained when 2-butyne undergoes each of the following reaction sequences?
- a. 1. H2/Lindlar catalyst 2. Br2/CH2Cl2
- b. 1. Na/NH3(1iq), –78°C 2. Br2/CH2Cl2
- c. 1. Cl2/CH2Cl2 2. Br2/CH2Cl2
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What stereoisomers are obtained when 2-butyne undergoes each of the following reaction sequences?
a. 1. H2/Lindlar catalyst 2. Br2/CH2Cl2 b. 1. Na/NH3(liq), –78 °C 2. Br2/CH2Cl2
c. 1. Cl2/CH2Cl2 2. Br2/CH2Cl2
1. Predict the major organic product(s) for each of the following reactions. Be sure to clearly indicate
the proper stereochemical relationships between groups (if appropriate), and write the word
"racemic" next to any compound that is formed as a racemic mixture.
a.
b.
C.
d.
H
H3C
CH3
aq. KOH, A
H₂N
CH3
OH
CH3
HO
Ph
H
CH3OH
PhH, A
+
Ph 'N'
H
CH3
HS
SH
BF3
teYr + {,,trs,£
CH3
H3C
H
e.
HO
N
H2SO4
Ph.
CH3
f.
CH3
p-TSOH
H3C
H
2 eq. CH3OH
g.
h.
H3C
Ph
H3O+
Ph
H
HO-NH2
AcOH
2. Predict the major organic product(s) for each of the following reactions. Be sure to clearly indicate
the proper stereochemical relationships between groups (if appropriate), and write the word
"racemic" next to any compound that is formed as a racemic mixture.
a.
b.
Ph
CH3
CH3
C.
☑
OH
d.
NaOH
H₂O
+
Мон
H2SO4
OH
CH2N2
Et2O
CH3
DCC
H3C
OH
Ph
NH2
Chapter 7 Solutions
Organic Chemistry (8th Edition)
Ch. 7.1 - Prob. 1PCh. 7.1 - Name the following:Ch. 7.1 - What is the molecular formula for a monocyclic...Ch. 7.1 - Draw the condensed and skeletal structures for...Ch. 7.1 - Draw the structure and give the common and...Ch. 7.2 - Prob. 6PCh. 7.2 - Name the following:Ch. 7.3 - What orbitals are used to form the carbon-carbon ...Ch. 7.4 - Prob. 9PCh. 7.4 - Why does cis-2-butene have a higher boiling point...
Ch. 7.6 - Prob. 12PCh. 7.6 - Prob. 13PCh. 7.7 - Prob. 14PCh. 7.7 - Which alkyne should be used for the synthesis of...Ch. 7.7 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.8 - Only one alkyne forms an aldehyde when it...Ch. 7.9 - Describe the alkyne you should start with and the...Ch. 7.9 - Prob. 20PCh. 7.10 - Prob. 21PCh. 7.10 - Prob. 22PCh. 7.10 - Prob. 23PCh. 7.10 - Rank the following from strongest base to weakest...Ch. 7.10 - Prob. 26PCh. 7.12 - Prob. 28PCh. 7 - What is the major product obtained from the...Ch. 7 - Draw a condensed structure for each of the...Ch. 7 - A student was given the structural formula of...Ch. 7 - Prob. 32PCh. 7 - What is each compounds systematic name?Ch. 7 - What reagents should be used to carry out the...Ch. 7 - Prob. 35PCh. 7 - Draw the mechanism for the following reaction:Ch. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - What is the major product of the reaction of 1 mol...Ch. 7 - Answer Problem 39, parts a-b, using 2-butyne as...Ch. 7 - What is each compounds systematic name? a....Ch. 7 - What is the molecular formula of a hydrocarbon...Ch. 7 - a. Starting with 3-methyl 1-butyne, how can you...Ch. 7 - Prob. 44PCh. 7 - Which of the following pairs are keto-enol...Ch. 7 - Prob. 46PCh. 7 - Do the equilibria of the following acid-base...Ch. 7 - What is each compounds systematic name?Ch. 7 - What stereoisomers are obtained when 2-butyne...Ch. 7 - Prob. 50PCh. 7 - Draw the keto tautomer for each of the following:Ch. 7 - Show how each of the following compounds can be...Ch. 7 - A chemist is planning to synthesize 3-octyne by...Ch. 7 - Prob. 54PCh. 7 - What stereoisomers are obtained from the following...Ch. 7 - Prob. 56PCh. 7 - Prob. 57PCh. 7 - Prob. 58PCh. 7 - Show how the following compound can be prepared...Ch. 7 - Prob. 60P
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