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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4. Circle any n-conjugated portions in the molecules below. Draw all resonance structures for each
conjugated molecule.
OCH3
H2C=CH-C=N
CH3
CH2
H2C
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.
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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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- 7. Draw curved arrows indicating the movements of electrons between the following pair of resonance structures. Name the pattern of resonance shown. What is the hybridization of the carbon atoms? 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" HO HOarrow_forwardH3C H. NHCH3 NHCH3 H Harrow_forwardH B) In the molecule above, how many electrons are involved in delocalization? Circle where the electron density is.arrow_forward
- We're starting to get a little bit more difficult! Remember the rules from the earlier problems. Type the correct name for the branched alkane whose structure is shown below. X Pay close attention to spelling here!arrow_forwardDraw the most and least stable Newman projections for the following molecules ( focus on C2 and C3). a. 2-chloro-2- fluoropentane b. 2,2-dimethylbutane C. 2-chloro-2-methylpentane d. 1,2-dibromoethanearrow_forwardA student suggests that the molecule on the right can be made from a single molecule with one less ring in it. If the student is correct, draw the starting material below, otherwise, check the box under the drawing area. ? + NaOH Click and drag to start drawing a structure. olo Ararrow_forward
- a) This alkene can be prepared via Wittig reaction. Draw structural formulas for the aldehyde and the Wittig reagent. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Draw the Wittig reagent in the ylide form. • If more than one combination of Wittig reagent and aldehyde is possible, draw only one set. b) How would you convert the alkene to a epoxide? MCPBA c) How many chiral centers are present in the epoxide? V How many stereoisomers are possible in the epoxide that you formed in b)?arrow_forwardI'm looking for an alkene with a single methyl group and an anti markovnikov Br at the last carbon and the markovnikov with Br on the bottom. The image is attached is just to illustrate positioning of the Br, and not an actual alkenearrow_forwarda) This alkene can be prepared via Wittig reaction. Draw structural formulas for the aldehyde and the Wittig reagent. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Draw the Wittig reagent in the ylide form. • If more than one combination of Wittig reagent and aldehyde is possible, draw only one set.arrow_forward
- First, add curved arrow(s) to show the resonance using the following pattern: an allylic carbocation. Modify the second structure given to draw the new resonance structure. Include lone pairs and charges in your structure. Use the + and - tools to add charges to an atom, and use the single bond tool to add/remove double bonds. .CH3 .CH3 ČH3arrow_forwardCircle the molecules that are most stable.arrow_forwardQ, Rotate your molecule so that you can see what the rat is looking at below. Draw the Newman projection (in box Q) to indicate what you are looking at.arrow_forward
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