Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 7, Problem 10CTQ
Interpretation Introduction
Interpretation: The axial methyl group should be circled for each given cyclohexane.
Concept introduction: In cyclohexane, all the six carbons are sp3 hybridized so, the expected angle for the connected atoms will be
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Build a model of 2,2,5,5-tetramethylhexane.
Orient the model so that you are looking at the carbon with the arrow pointing to it in Figure 3. Align the bond to the next carbon in the chain so that it is directly behind the first carbon to match a Newman projection view. (See Figure MM.3 in the lab manual)
Spin the carbons on either side of the bond you're looking down to cycle through all three staggered and all three eclipsed positions of the substituents.
Draw all six positions as Newman projections on the data sheet and identify the position with the highest energy. Draw the six Newman projections of all of the different energy levels. Label each as staggered or eclipsed and rank in order from lowest energy to highest.
7. Draw curved arrows indicating the movements of electrons between the following pair of
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8. Draw the remaining three resonance structures for the molecule in problem 7 above.
9. There are several possible forms of a trisubstituted cyclohexane with the formula C10H200. I
have drawn four of them. From these, which one do you think is most commonly naturally
occurring, and why? Which is least commonly occurring and why?
HO
HO"
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HO
What is the preferred IUPAC name of the alkyne in Figure 2? [Numbers are separated by commas and numbers and letters by hyphens. Use lowercase letters and do not use spaces.] *
Your answer
Chapter 7 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 7 - Prob. 1CTQCh. 7 - Prob. 2CTQCh. 7 - Prob. 3CTQCh. 7 - Draw wedge and dash skeletal representations of...Ch. 7 - Label each ring in Figure 7.2 cis or trans.Ch. 7 - Prob. 6CTQCh. 7 - Prob. 7CTQCh. 7 - Prob. 8CTQCh. 7 - a model of cyclohexane in a chair conformation,...Ch. 7 - Prob. 10CTQ
Ch. 7 - Prob. 11CTQCh. 7 - Fill in the blanks: cis-1,3-Dimethylcyclohexane...Ch. 7 - Prob. 13CTQCh. 7 - Prob. 14CTQCh. 7 - Prob. 15CTQCh. 7 - Prob. 16CTQCh. 7 - Prob. 17CTQCh. 7 - Prob. 18CTQCh. 7 - Draw chair representations of...Ch. 7 - Which stereoisomer in the previous question is...Ch. 7 - Prob. 21CTQCh. 7 - Prob. 1ECh. 7 - Label each of the following as cis, trans or...Ch. 7 - Which pair has more in common with one another?Ch. 7 - Prob. 4ECh. 7 - Prob. 5ECh. 7 - Prob. 6ECh. 7 - Fill in the table by drawing a representation of a...Ch. 7 - Prob. 9ECh. 7 - True or False: If you perform a chair flip on...Ch. 7 - Prob. 11ECh. 7 - Prob. 12ECh. 7 - Prob. 13ECh. 7 - Prob. 14ECh. 7 - Prob. 15ECh. 7 - Draw trans-1-tert-butyl-3-methylcyclohexane in its...Ch. 7 - Build a model of methylcyclohexane, and use the...
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