ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 4, Problem 4.19P
Consider rotation around the carbon-carbon bond in
a. Using Newman projections, draw all of the staggered and eclipsed conformations that result from rotation around this bond.
b. Graph energy versus dihedral angle for rotation around this bond
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Consider rotation around the carbon–carbon bond in 1,2-dichloroethane (ClCH2CH2Cl).
a.Using Newman projections, draw all of the staggered and eclipsed conformations that result from rotation around this bond.
b.Graph energy versus dihedral angle for rotation around this bond.
1. Considering compounds that have the same number of carbon atoms, explain why alkanes and cycloalkanes have different molecular formulas but alkenes and cycloalkanes have the same molecular formulas.
2. Draw the condensed or line-angle structure for an alkene with the formula C5H10.
3. Draw the condensed or line-angle structure for 4 more C5H10 isomers (2 additional alkenes and 2 cyclic isomers).
9) There are 3 different cyclopropane molecules with the formula GHĄC12.
a.
Draw and build the 3 molecules.
b. Below each drawing, name each molecule with correct nomenclature.
Label a pair that are constitutional isomers.
d. Label a pair that are stereoisomers (or configurational isomers).
С.
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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- 8. With the model kits, make a model for the two cycloalkanes shown in Figure 3. Hold or overlap the models on top of each other to see if they can be superimposed or not. Figure 3: Br Br H Brarrow_forwardLook at a cyclohexane model:a. Mark the axial bonds. Hold carbon atoms 1, 2, 3, 4, 5, and 6 firmly and flip up carbon 4. What is the resulting conformation? b. Then holding carbons 2, 3, 4, 5, and 6 firmly, flip down carbon What is now the resulting conformation?arrow_forwardAnalyze the two Newman projections and determine the relationship between the two. How would you describe the relation between conformations when they are maintained at a temperature too low to permit them to interconvert? CH3 CH3 Br. H H H H A. Identify the relationship. They are identical. They are structural isomers. They are stereoisomers. They are conformers. H H -I H Br H B. What is the relationship at low temperatures? They are identical. They are conformational diastereomers. They are structural isomers. They are conformational enantiomers.arrow_forward
- a. Which of the following compounds can exist as cis–trans isomers? b. For those compounds that can exist as cis and trans isomers, draw and label the isomers. 1. CH3CH=CHCH2CH2CH3 2. CH3CH2C-CH2CH3=CHCH3 3. CH3CH CHCH3 4. CH3CH2CH CH2arrow_forwardQUESTION 4 Compare Structure A and Structure B. H. H. H. Structure A Structure B Do these structures depict the same molecule, different molecules, or are they constitutional isomers? Choose the best description for the relationship between these two structures. (Hint: Convert both Newman projections to wedge-dash structures and compare their connectivity.) O A. The two structures depict the same molecule but in different conformations. O B. The two structures depict the same molecule and they are both in the same conformation. O C. These two molecules are constitutional isomers. O. D. These two molecules are not isomers. They have different molecular formulas.arrow_forwardHexane is a hydrocarbon with multiple isomers. Rank these isomers in order of decreasing boiling points. (Make sure you can justify your reasoning.) II III A. I > || > II B. I> III >|| C. I| > I > II D. II > I >|| E. III > || > Iarrow_forward
- Interconversion of the staggered and eclipsed conformations of alkanes requires rotation around a -C bond such as the one depicted below (see arrow). Using your knowledge of bonding, explain why these rotations do not significantly affect the energy (strength) of these bonds. You may find it helpful to describe the type of bond being rotated.arrow_forwardBb.13.arrow_forwardConsider rotation around the carbon–carbon bond in 1,2-dichloroethane (ClCH2CH2Cl).Using Newman projections, draw all of the staggered and eclipsed conformations thatresult from rotation around this bond.Graph energy versus dihedral angle for rotation around this bond.arrow_forward
- Draw the line bond structures of following types of hydrocarbons using four carbon atoms: Can you explain to me about this part A: two noncyclic alkanes, please? Can you explain to me about this part B: two cycloalkanes, please?arrow_forwardThe dimethylcyclohexane with the structure shown below is: ÇH3 CH3 Select one: O a. a trans isomer with the CH3 groups in axial positions. O b. a cis isomer with the CH3 groups in equatorial positions. O c. a cis isomer with the CH3 groups in equatorial and axial positions. O d. a trans isomer with the CH3 groups in equatorial positions.arrow_forwardButane is an unbranched alkane with the condensed structure CH,CH,CH,CH,. Draw the complete structure of butane. Show all hydrogen atoms. Select Draw Rings More C H Draw the skeletal structure of butane in line-bond (line-angle) mode. Do not show hydrogen atoms. Select Draw Rings More Carrow_forward
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