Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 4, Problem 4.64P
Draw the three constitutional isomers having molecular formula
two methyl groups as substituents. For each constitutional isomer that can have cis and trans isomers, draw
the two stereoisomers.
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Draw the three constitutional isomers having molecular formula C7H14 that contain a ve-membered ring and two methyl groups as substituents. For each constitutional isomer that can have cis and trans isomers, draw the two stereoisomers.
Draw all six ketone constitutional isomers of the formula C6H12O
Follow the instructions and draw the five different possible arrangements of six carbon units. For parts A-C, draw only the six carbon atoms and Do Not draw the ketone.
A:draw the structure containing six carbons in the longest parent chain.
B: draw the two structures containing five carbons in the longest parent chain.
C: Draw the two structures containing four carbons in the longest parent chain.
D: Using the five structures from parts A,B,&C as a guide, draw the skeletal structures of the six constitutional isomers of C6H12O that are ketones.
A
CH3
***
CH3
E
6
74
CH3
trans
trans
Cis
Cis
4. Draw a constitutional isomer and a stereoisomer of the compound below.
CH₂
A
CH3
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 4.1PCh. 4 - Prob. 4.2PCh. 4 - (a) Classify the carbon atoms in each compound as...Ch. 4 - Problem 3.3 Classify a carbon atom by the number...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.6PCh. 4 - Prob. 4.7PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Give the IUPAC name for each compound. a. c. b. ...Ch. 4 - Give the IUPAC name for each compound. a....
Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.12PCh. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.17PCh. 4 - a.Draw the three staggered and three eclipsed...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Prob. 4.23PCh. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.26PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.29PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.32PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.35PCh. 4 - 3.31 For each alkane: (a) classify each carbon...Ch. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Give the IUPAC name for each compound. a. h.k....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.42PCh. 4 - Prob. 4.43PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - Considering rotation around the bond highlighted...Ch. 4 - Prob. 4.49PCh. 4 - Prob. 4.50PCh. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - Prob. 4.52PCh. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.59PCh. 4 - Prob. 4.60PCh. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.62PCh. 4 - Prob. 4.63PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Which of the following compounds are lipids?Ch. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.74PCh. 4 - Prob. 4.75PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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- 3) Draw a cyclohexane chair with 3 substituents in the most stable conformation. Explain why the conformation you've chosen is the most stable.arrow_forward5a. Draw a Newman Projection for the following compound. 5b. Rotation about the C3 – C4 bond in conformer 1 leads to two less stable staggered conformers. Draw a Newman Projection for one of these less stable conformers, as viewed down the C3 to C4 bond. What is the single highest energy gauche interaction in the Newman Projection?arrow_forwardFollowing is the Structural formal of Chloropropane H H H 2. H Draw Newman projections for all staggered and eclipsed conformation formed by rotation about C1 - C2 bond from 0° to 360°. b) Which Staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy, which has thhe highest energy?arrow_forward
- 4. Which structure below represents the most stable conformation of cis-1-t-butyl-4-methylcyclohexane? A B D 5. The planar form of which ring would have bond angles close to the tetrahedral value, but is destabilized by eclipsing interactions (torsional strain)? Which of the following statements about conformations is FALSE? A) Conformations can be isolated and separated at room temperature B) Conformations are interconverted by rotation about o-bonds C) For butane the staggered anti conformation is the most stable D) For ethane the eclipsed conformation is the least stable 6. 7. Which of the following compounds has two chirality centers? .H H. H3Carrow_forwardSight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forward5. Draw the two chair conformations ("ring filips") of trans –1- ethyl-4-methylcyclohexane to show the axial and equatorial substituents (including all hydrogens). Then determine which of the two conformations is more stable and why.arrow_forward
- 5. Draw Newman projections of all of the major conformations of 2,3,5-trimethylhexane, sighting along the C2-C3 bond. Identify the most stable and least stable conformations.arrow_forwardStarting from the Newman projection below, rotate the back carbon to provide the structure in the least stable conformation. CH3 H Ø H CH3 CH3 H H H H H Harrow_forward1. Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2 ¬ C3 bond (b) 3,3-dimethylhexane about the C3 ¬ C4 bond2. refer to the questions below:arrow_forward
- Considering structures below, which of the following statements is true? O I H-C-O-CH₂ CH₂OH O || II HOCH₂CH₂-C-OH III HOCH₂CH₂-O-C-H A) I and II have different molecular formulas. B) I and III are structural isomers of each other. C) II and III are stereoisomers of each other. D) II and III are different conformations of the same compound. E) I and III are the same compound.arrow_forwardUse a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2¬C3 bondarrow_forwardDraw the Newman projection so that it corresponds to the molecule and conformation shown when viewed down the red bond in the direction of the arrow. H I H CH3 X 5 Carrow_forward
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