Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 3, Problem 39P
(a)
Interpretation Introduction
Interpretation: The initiation, propagation and termination step of treatment of methane with hydrogen peroxide should be written and
Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive then system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction
(b)
Interpretation Introduction
Interpretation: The value of
Concept introduction:Thermodynamics is a study of energy transfers that can be done by either heat or work. The energy transferred through work involves force. When work is positive, the system gains energy while when work is negative then system loses energy. Heat is not a state function and therefore change in enthalpy of reaction
(c)
Interpretation Introduction
Interpretation: The value of
Concept introduction:Hammond postulate states that exothermic reactions are characterized by early transition states that resemble the structure of substrate more than the product. Slow or endothermic processes are characterized by late transition states that resemble the almost formed bonds as in the products.
(d)
Interpretation Introduction
Interpretation: The reaction that is faster among reaction of methane with chlorine or peroxide should be identified.
Concept introduction:Hammond postulate states that exothermic reactions are characterized by early transition states that resemble the structure of substrate more than the product. Slow or endothermic processes are characterized by late transition states that resemble the almost formed bonds as in the products.The energy profile diagram relates the barrier required to attain a transition state as illustrated below:
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H3C
CH3
H3C
NA C→XT
Br
Br₂
CH₂Cl₂
H3C
Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic
intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂.
CH3
Br
In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion
to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the
bromonium ion so that a product with anti stereochemistry is formed.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Br
CH3
H3C
CH3
2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.
Free radical halogenation is used to replace one or more hydrogens on an alkane with one or more halogens (either chlorine or bromine). It is a substitution reaction. A student performs a free radical bromination on 3-methyl-pentane (5.88 g) to create the desired product of 3-bromo-3-methyl-pentane. The product mix, which hopefully contains almost all 3-bromo-3-methyl-pentane, is cleaned up by passing it through a gas chromoatograph, which separates out the 3-bromo-3-methyl-pentane from any undesired products made during the reaction (undesired products are created frequently in free radical halogenation). The initial product mix weighed 9.45 g; the purified 3-bromo-3-methyl-pentane weighed 7.21 g. What is the student's percent recovery?
Chapter 3 Solutions
Organic Chemistry: Structure and Function
Ch. 3.1 - Prob. 3.2TIYCh. 3.1 - Prob. 3.3ECh. 3.4 - Prob. 3.5TIYCh. 3.5 - Prob. 3.6ECh. 3.7 - Prob. 3.7ECh. 3.7 - Prob. 3.9TIYCh. 3.9 - Prob. 3.11TIYCh. 3.11 - Prob. 3.12ECh. 3 - Prob. 15PCh. 3 - Prob. 16P
Ch. 3 - Prob. 17PCh. 3 - Prob. 18PCh. 3 - Prob. 19PCh. 3 - Prob. 20PCh. 3 - Prob. 21PCh. 3 - Prob. 22PCh. 3 - Prob. 23PCh. 3 - Prob. 24PCh. 3 - Prob. 25PCh. 3 - Prob. 26PCh. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Prob. 29PCh. 3 - Prob. 30PCh. 3 - Prob. 31PCh. 3 - Prob. 32PCh. 3 - Prob. 33PCh. 3 - Prob. 34PCh. 3 - Prob. 35PCh. 3 - Prob. 36PCh. 3 - Prob. 37PCh. 3 - Prob. 38PCh. 3 - Prob. 39PCh. 3 - Prob. 40PCh. 3 - Prob. 41PCh. 3 - Prob. 42PCh. 3 - Prob. 43PCh. 3 - Prob. 44PCh. 3 - Prob. 45PCh. 3 - Prob. 46PCh. 3 - Prob. 47PCh. 3 - Prob. 48PCh. 3 - Prob. 49PCh. 3 - Prob. 50PCh. 3 - Prob. 51P
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