Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 3.SE, Problem 53AP
Interpretation Introduction
Interpretation:
The
Concept introduction:
Simvastatin
Formula: C25H38O5
Pravastatin
Formula: C23H36O7
Pravastatin (marketed as Pravachol or Selektine) is a member of the drug class of statins, used in combination with diet, exercise, and weight loss for lowering cholesterol and preventing cardiovascular disease.
Simvastatin, marketed under the trade name Zocor among others, is a lipid-lowering medication.
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13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the
molecule depicted below.
Bond B
Bond A
Bond C
a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in
appropriate boxes.
Weakest
Bond
Strongest
Bond
b. (4pts) Consider the relative stability of all cleavage products that form when bonds A,
B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B,
and C are all carbon radicals.
i. Which ONE cleavage product is the most stable? A condensed or bond line
representation is fine.
ii. Which ONE cleavage product is the least stable? A condensed or bond line
representation is fine.
c. (5pts) Use principles discussed in lecture, supported by relevant structures, to
succinctly explain the why your part b (i) radical is more stable than your part b(ii)
radical. Written explanation can be no more than one-two succinct sentence(s)!
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Statifically more chances to abstract one of these 6H
11. (10pts total) Consider the radical chlorination of 1,3-diethylcyclohexane depicted below. 4
4th total
• 6H total
래
• 4H total
21 total
ZH
2H
Statistical
H < 3° C-H weakest
-
product
abstraction here
bund
leads to thermo favored
a) (6pts) How many unique mono-chlorinated products can be formed and what are the
structures for the thermodynamically and statistically favored products?
Product
6
Number of Unique
Mono-Chlorinated Products
Thermodynamically
Favored Product
Statistically
Favored Product
b) (4pts) Draw the arrow pushing mechanism for the FIRST propagation step (p-1) for the
formation of the thermodynamically favored product. Only draw the p-1 step. You do
not need to include lone pairs of electrons. No enthalpy calculation necessary
H
H-Cl
Waterfox
10. (5pts) Provide the complete arrow pushing mechanism for the chemical transformation →
depicted below
Use proper curved arrow notation that explicitly illustrates all bonds being broken, and
all bonds formed in the transformation.
Also, be sure to include all lone pairs and formal charges on all atoms involved in the
flow of electrons.
CH3O
II
HA
H
CH3O-H
H
①
Chapter 3 Solutions
Organic Chemistry
Ch. 3.1 - Prob. 1PCh. 3.1 - Prob. 2PCh. 3.1 - Identify the functional groups in the following...Ch. 3.2 - Draw structures of the five isomers of C6H14.Ch. 3.2 - Propose structures that meet the following...Ch. 3.2 - Prob. 6PCh. 3.3 - Draw the eight 5-carbon alkyl groups (pentyl...Ch. 3.3 - Identify the carbon atoms in the following...Ch. 3.3 - Prob. 9PCh. 3.3 - Prob. 10P
Ch. 3.4 - Give IUPAC names for the following compounds:Ch. 3.4 - Prob. 12PCh. 3.4 - Name the eight 5-carbon alkyl groups you drew in...Ch. 3.4 - Give the IUPAC name for the following hydrocarbon,...Ch. 3.7 - Make a graph of potential energy versus angle of...Ch. 3.7 - Sight along the C2-C1 bond of 2-methylpropane...Ch. 3.7 - Sight along the C2-C3 bond of 2,3-dimethylbutane,...Ch. 3.7 - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 19VCCh. 3.SE - Prob. 20VCCh. 3.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 22APCh. 3.SE - Prob. 23APCh. 3.SE - Propose structures for the following: (a) A...Ch. 3.SE - Prob. 25APCh. 3.SE - Draw the structures of the following molecules:...Ch. 3.SE - Draw structures that meet the following...Ch. 3.SE - Prob. 28APCh. 3.SE - In each of the following sets, which structures...Ch. 3.SE - There are seven constitutional isomers with the...Ch. 3.SE - Prob. 31APCh. 3.SE - Draw compounds that contain the following: (a) A...Ch. 3.SE - Prob. 33APCh. 3.SE - Draw and name all monochloro derivatives of...Ch. 3.SE - Draw structures for the following: (a)...Ch. 3.SE - Prob. 36APCh. 3.SE - Draw a compound that: (a) Has nine primary...Ch. 3.SE - Give IUPAC names for the following compounds:Ch. 3.SE - Name the five isomers of C6H14.Ch. 3.SE - Explain why each of the following names is...Ch. 3.SE - Prob. 41APCh. 3.SE - Consider 2-methylbutane (isopentane). Sighting...Ch. 3.SE - What are the relative energies of the three...Ch. 3.SE - Construct a qualitative potential-energy diagram...Ch. 3.SE - Prob. 45APCh. 3.SE - Draw the most stable conformation of pentane,...Ch. 3.SE - Draw the most stable conformation of...Ch. 3.SE - Prob. 48APCh. 3.SE - Prob. 49APCh. 3.SE - Formaldehyde, H2C=O, is known to all biologists...Ch. 3.SE - Prob. 51APCh. 3.SE - Increased substitution around a bond leads to...Ch. 3.SE - Prob. 53APCh. 3.SE - In the next chapter we'll look at...Ch. 3.SE - We’ll see in the next chapter that there are two...
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