ORG CHEM CONNECT CARD
6th Edition
ISBN: 9781264860746
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 13, Problem 54P
Consider the following bromination:
a. Calculate
b. Draw out a stepwise mechanism for the reaction, including the initiation, propagation, and termination steps.
c. Calculate
d. Draw an energy diagram for the propagation steps.
e. Draw the structure of the transition state of each propagation step.
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Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction.
•
•
You do not have to consider stereochemistry.
•
Include all valence lone pairs in your answer.
Br2
Br
In cases where there is more than one answer, just draw one.
+
√n [
?
N
ZI
Consider this step in a radical reaction:
Br
Br:
?
Reaction coordinate diagrams:
Two-step diagram. Label the reactant (R), product (P), intermediate (I"), and transition
states (TS; and TS2), plus the axis with appropriate units/labels.
1) Break the diagram up into 2
steps. Which one is the slow
step? The fast step?
2) Endothermic or exothermic?
Suppose a
is added to step one. Sketch the effect of this
addition on the diagram.
You can identify the intermediates and
by remembering:
Intermediates are
and then
Catalysts are added to a reaction (like a reactant), and are
at the end.
Practice: Identify the reactants, products, intermediate(s), and catalyst(s). Put a star next to
the rate-determining step.
Step 1
A+B AB
(fastest)
Step 2
C + AB → ABC
Step 3
ABC + D→ ACD + B
(fast)
diy
Chapter 13 Solutions
ORG CHEM CONNECT CARD
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - Prob. 4PCh. 13.3 - Prob. 5PCh. 13.4 - Prob. 7PCh. 13.5 - Problem 15.8 Which bond in the each compound is...Ch. 13.6 - Prob. 9PCh. 13.6 - Prob. 10PCh. 13.7 - Prob. 11P
Ch. 13.7 - Prob. 12PCh. 13.8 - Prob. 13PCh. 13.8 - Prob. 14PCh. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 34PCh. 13 - 15.37 What alkane is needed to make each alkyl...Ch. 13 - 15.38 Which alkyl halides can be prepared in good...Ch. 13 - Prob. 37PCh. 13 - 15.40 Explain why radical bromination of p-xylene...Ch. 13 - a. What product(s) (excluding stereoisomers) are...Ch. 13 - Prob. 40PCh. 13 - 15.43 Draw the products formed when each alkene is...Ch. 13 - 15.44 Draw all constitutional isomers formed when...Ch. 13 - 15.45 Draw the organic products formed in each...Ch. 13 - Prob. 45PCh. 13 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 13 - 15.48 Draw the products formed in each reaction...Ch. 13 - 15.53 Consider the following bromination: .
a....Ch. 13 - 15.54 Draw a stepwise mechanism for the following...Ch. 13 - Prob. 57PCh. 13 - 15.57 Devise a synthesis of each compound from...Ch. 13 - Prob. 59PCh. 13 - Prob. 60PCh. 13 - 15.60 Devise a synthesis of each compound using ...Ch. 13 - Prob. 62PCh. 13 - Prob. 63PCh. 13 - 15.63 As described in Section 9.16, the...Ch. 13 - 15.64 Ethers are oxidized with to form...
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- 3. Yilong did this reaction below and got multiple products. Show the mechanism(s) and products. Be clear about stereochemistry. • If he put the products into a polarimeter, what kind of reading would he get? How are the molecules related? H3C 1) BH 3, THF 2) H2O2, NaOHarrow_forwardAs we will learn in Section 15.12, many antioxidants-compounds that prevent unwanted radical oxidation reactions from occurring-are phenols, compounds that contain an OH group bonded directly to a benzene ring. a. Explain why homolysis of the O-H bond in phenol requires considerably less energy than homolysis of the O-H bond in ethanol (362 kJ/mol vs. 438 kJ/mol). b. Why is the C-O bond in phenol shorter than the C-O bond in ethanol? -O-H CH,CH2-0-H phenol ethanolarrow_forwardDraw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CH3 CH3 CH3COCI/ AICI3 H₂C. You do not have to consider stereochemistry. Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one.arrow_forward
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