CHS Consider the radical halogenation reaction shown below to answer parts a-c. Note that "Ph" refers to a benzene ring. Bond BDE (kJ/mol) CH₂CH₂ H (CH₂), C-H PhCH₂-H CH₂CH₂-Br (H₂C),C-Br PhCH₂-Br CH3 H Br₂, heat Major Organic + HBr Product CH3 a. Draw the major monobrominated organic product for the reaction. B1₂ + HBC H-Br Br-Br 368-378-10 kj mol 423 404 378 303 304 264 368 190 (H-BC)-(CH₂-H) c. Calculate AHD for the first propagation step for this reaction. Show your work and include units. d. Calculate AH° for the second propagation step for this reaction. Show your work and include units. (CH₂-Br)_ (Br-Br)
CHS Consider the radical halogenation reaction shown below to answer parts a-c. Note that "Ph" refers to a benzene ring. Bond BDE (kJ/mol) CH₂CH₂ H (CH₂), C-H PhCH₂-H CH₂CH₂-Br (H₂C),C-Br PhCH₂-Br CH3 H Br₂, heat Major Organic + HBr Product CH3 a. Draw the major monobrominated organic product for the reaction. B1₂ + HBC H-Br Br-Br 368-378-10 kj mol 423 404 378 303 304 264 368 190 (H-BC)-(CH₂-H) c. Calculate AHD for the first propagation step for this reaction. Show your work and include units. d. Calculate AH° for the second propagation step for this reaction. Show your work and include units. (CH₂-Br)_ (Br-Br)
Chemistry
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
Question
Transcribed Image Text:1. Consider the radical halogenation reaction shown below to answer parts a-c. Note that "Ph"
refers to a benzene ring.
BDE (kJ/mol)
CHS
Hs
CH3
•CH3
e.
Br₂, heat
a Draw the major monobrominated organic product for
the reaction.
Major
Organic
Product
+ HBC
+HBr
368-378-10 kj
mol
Statistical
(H-B()-(CH₂-H)
C. Calculate AH° for the first propagation step for this reaction. Show your work and
include units.
Experimental Yield
(%)
Selectivity
Bond
CH₂CH₂-H
(CH₂)3C-H
PhCH₂-H
CH₂CH₂-Br
d. Calculate AH° for the second propagation step for this reaction. Show your work and
include units. (CHz-Br) - (B(-pr)
(H₂C) C-Br
PhCH₂-Br
H-Br
Br-Br
RC
423
404
378
303
304
264
368
190
2641 Kj/md-190kj/mol = 74kj/mol
Draw a reaction coordinate diagram for the two-step propagation cycle for the reaction.
Include the two AH values that you calculated previously in the diagram. Label the rate-
determining step. Label each step as exothermic or endothermic.
f. Draw the transition state for the rate-determining step. Does the transition state look most
like the alkane starting material, the radical intermediate, or halogenated product?
Explain your answer. (Hint: Hammond Postulate.)
g. Bromination is 80x more selective for the secondary position than the primary position.
Using this information, complete the chart and determine what percentage of the
experimental product yield will have substitution at each position. Only consider
monobromination products.
Primary
Secondary
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