ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 4.10, Problem 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. 4.1 - Prob. 1PCh. 4.1 - Problem 4.2 Which of the following is not another...Ch. 4.1 - Problem 4.3 Draw the five constitutional isomers...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.2 - Draw the five constitutional isomers that have...Ch. 4.4 - Problem 4.7 Give the IUPAC name for each...Ch. 4.4 - Give the IUPAC name for each compound. a....Ch. 4.4 - Problem 4.9 Give the structure corresponding to...Ch. 4.4 - Prob. 10P
Ch. 4.5 - Give the IUPAC name for each compound.Ch. 4.5 - Give the structure corresponding to each IUPAC...Ch. 4.8 - Arrange the following compounds in order of...Ch. 4.9 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4.9 - Prob. 15PCh. 4.9 - Prob. 16PCh. 4.10 - Problem 4.17 a. Draw the three staggered and...Ch. 4.10 - Problem 4.18 Rank the following conformations in...Ch. 4.10 - Problem 4.19 Consider rotation around the...Ch. 4.10 - Calculate the destabilization present in each...Ch. 4.12 - Problem 4.21 Classify the ring carbons as up or...Ch. 4.12 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4.13 - Draw a second chair conformation for each...Ch. 4.13 - Problem 4.24 Draw both conformations for and...Ch. 4.13 - Problem 4.25 Draw the structure for each compound...Ch. 4.13 - Prob. 26PCh. 4.14 - Prob. 31PCh. 4.14 - Prob. 32PCh. 4.15 - Prob. 33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 42PCh. 4 - 4.46 Considering rotation around the bond...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 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 66PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 74PCh. 4 - Prob. 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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- 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_forwardThe complete answer.arrow_forwardReplace one of the H atoms in the ethane model with a Br atom, to form ethyl bromide CH3CH2Br, and draw a projection (lewis) and a perspective drawing. Does replacing different hydrogen atoms in CH3CH3 to produce Ch3CH2br give you different isomers? (i.e. Are all the hydrogen atoms equivalent?) How many isomers of CH3CH2Br can you construct? Make a model of one other conformer of CH3CH2Br. DId you need to break any bonds to form the second conformer from the first?arrow_forward
- 1. Does chlorophyll a or chlorophyll b have a greater number of “conjugated” double bonds, or do they have the same number? Draw the structure of chlorophyll b and using a colored highlighter, indicate which of the double bonds are “conjugated”. 2. What is the main functional group in THF (tetrahydrofuran)? Is THF more polar or less polar than IPA (also called: isopropyl alcohol, isopropanol, or 2-propanol)? 3.If you mistakenly used hexanes-THF (2:1) for eluting the carotene pigments from your chromatography column, will they elute faster or slower than if you had correctly used hexanes-THF (10:1)? Explainarrow_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_forwardConstitutional isomers are compounds which have the same molecular formula but different structural formulae. They are different compounds with different physical and chemical properties.a. Rearrange your model of n-hexane to make as many possible isomers of C6H14 as you can. Draw the structural formula and write down the IUPAC name for each isomer that you make.b. Constitutional isomers can also have different functional groups. Make all possible isomers of C3H8O. Write down the structural formulae and IUPAC names for all the compounds you make. Hint: Consider alcohol and ether functional groups.arrow_forward
- Hexane 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_forwardConsider the energy diagram showing the conformational analysis of propane. Select the number that corresponds to the correct conformation. úr H. H energy H 180 HH H CH3 H. ***** H H H CH3 CH3 0 dihedral angle H H HCH3 H H 180 IV HCH3 H H V CH 3arrow_forwardThe octane rating for gasoline is a measurement of how readily a fuelcombusts compared to 2,2,4-trimethylpentane, an isomer of octane.a. Draw 2,2,4-trimethylpentane and verify that it is an isomer ofoctane.b. Draw four other isomers of octane.c. Select one of the isomers and draw it such that it looksdifferent on the page but is still the exact same compound.d. Name this isomer.e. Define isomer using a complete sentence.arrow_forward
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