ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 4, Problem 4.62P
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.
3) Draw a cyclohexane chair with 3 substituents in the most stable conformation. Explain why the
conformation you've chosen is the most stable.
Chapter 4 Solutions
ORGANIC CHEMISTRY
Ch. 4 - Prob. 4.1PCh. 4 - Problem 4.2 Which of the following is not another...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Problem 4.7 Give the IUPAC name for each...Ch. 4 - Give the IUPAC name for each compound. a....Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.10P
Ch. 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. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...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 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound.
a. c....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. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 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. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 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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- Draw the structure(s) of the cycloalkanes with molecular formula C6H12 that have a 3-membered ring and two substituents.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_forwardA CH3 *** CH3 E 6 74 CH3 trans trans Cis Cis 4. Draw a constitutional isomer and a stereoisomer of the compound below. CH₂ A CH3arrow_forward
- 2 1 Group activity: Use molecular model to convert the given 3D perspective structure to Newman projection around C-C bond on the template provided. Fill in the substituent for the most stable conformation in the templates provided. H H OH Br OH CH Y/ 3D of most stable conformation ΕΙ Fischer projection of most stable conformation most stable conformation Use the molecular model of chair conformation of cyclohexane and fill in the substituents in the template provided for chair conformation and complete the Newman projections showing only substituents for given molecules. Circle the chair conformation which is more stable. 1) cis-3-isopropylcyclohexanol 2) trans-3-Isopropylcyclohexaol QOarrow_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_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_forward
- 5. 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_forwardDraw a Newman projection for two more staggered conformations of this molecule. Which of your conformations is most stable? Assume that -OH and -CH3 are comparable in size.arrow_forwardUsing a Newman projection and your knowledge of conformational analysis, draw the two limiting conformations of TMS(Tetramethylsilane) along any C-Si bond (Lowest energy Highest energy conformation)arrow_forward
- Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2¬C3 bondarrow_forward11. Which one of these forms of 1,2,4-trimethylcyclohexane can have a chair conformation in which the methyl groups are all equatorial? III ++ |||| A B с D Earrow_forwardQuestion 1: 1,4-dimethylcyclohexane can exist in two diastereomeric forms, cis and trans. The structures of these two isomers are shown below, along with their two chair conformations, each of which have been numbered (I-IV). H₂C CH3 Blank 1 CH3 Blank 2 CH3 Blank 3 CH3 -CH3 Add your answer CH3 Add your answer H₂C Add your answer CH3 CH3 Identify the correct order of chair conformation stability by filling in the blanks using either a sign of inequality () or a sign of equality (=) if two structures are energetically equivalent. MOST STABLE IV Blank 1 | Blank 2 Il Blank 3 III LEAST STABLE ... CH3 III -CH3 IVarrow_forward
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