Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 5.9, Problem 12P
Carbocations are key intermediates in petroleum refining. Of particular importance is one having the carbon skeleton shown.
How many different
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N,N-diethyl-m-toluamide (DEET) is the active ingredient in many insect repellent preparations. Following is one of the steps in its synthesis. In the box below draw the
structure of the product of this reaction.
H3C
MgBr
1. CO₂
2. H₂O*
product
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Draw the Grignard reagent as a covalent magnesium bromide.
N,N-diethyl-m-toluamide (DEET) is the active ingredient in many insect repellent preparations. Following is one of the steps in its synthesis. In the box below
draw the structure of the product of this reaction.
H3C
MgBr
1. CO2
2. H30*
product
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Draw the Grignard reagent as a covalent magnesium bromide.
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Draw all the isomers of C5H₁0. Clearly show stereochemistry if stereoisomers are possible.
Step 1: Start by drawing all the isomers with double bonds.
• Consider constitutional isomers, then stereoisomers.
Step 2: Draw all isomers containing a ring.
• Consider constitutional isomers, then stereoisomers.
Step 2: Next consider isomers containing a ring. The largest ring possible with this molecular formula contains 5 carbons, while
the smallest possible ring contains 3 carbons.
Draw an isomer containing a 5-carbon ring.
Rings More
Select Draw
/
C
H
Erase
Consider a 4-carbon ring of C5H₁0. Draw stereoisomers,
if applicable.
Select Draw Rings
More
C
H
Erase
Chapter 5 Solutions
Organic Chemistry - Standalone book
Ch. 5.1 - Prob. 1PCh. 5.1 - Prob. 2PCh. 5.1 - Many compounds contain more than one functional...Ch. 5.2 - Prob. 4PCh. 5.3 - Prob. 5PCh. 5.4 - Classify the isomeric C4H10O alcohols as being...Ch. 5.5 - Bromine is less electronegative than chlorine, yet...Ch. 5.6 - Prob. 8PCh. 5.7 - Prob. 9PCh. 5.8 - Prob. 10P
Ch. 5.8 - Prob. 11PCh. 5.9 - Carbocations are key intermediates in petroleum...Ch. 5.9 - Prob. 13PCh. 5.9 - Prob. 14PCh. 5.11 - Prob. 15PCh. 5.13 - Prob. 16PCh. 5.14 - For the reaction of a primary alcohol RCH2OH with...Ch. 5.15 - Prob. 18PCh. 5 - Write structural formulas for each of the...Ch. 5 - Prob. 20PCh. 5 - Prob. 21PCh. 5 - Write structural formulas for all the...Ch. 5 - Prob. 23PCh. 5 - Prob. 24PCh. 5 - Epichlorohydrin is the common name of an...Ch. 5 - Prob. 26PCh. 5 - Prob. 27PCh. 5 - Prob. 28PCh. 5 - Some of the most important organic compounds in...Ch. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - The reaction of 2,2-dimethyl-1-propanol...Ch. 5 - (a) Assuming that the rate-determining elementary...Ch. 5 - The reaction of 3-tert-butyl-3-pentanol with...Ch. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46DSPCh. 5 - Prob. 47DSPCh. 5 - Prob. 48DSPCh. 5 - Prob. 49DSPCh. 5 - Prob. 50DSPCh. 5 - Prob. 51DSPCh. 5 - Prob. 52DSP
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