ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 4, Problem 4.53P
For each compound drawn below:
a. Label each
b. Classify each conformation as cis or trans.
c. Translate each structure into a representation with a hexagon for the six-membered ring, and wedges and dashed wedges for groups above and below the ring.
d. Draw the second possible chair condformation for each compound.
[1] 
[b] 
[c] 
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Part 1
1. Consider the structure below and draw its most stable and least stable conformations
in Newman Projections while looking down the bond indicated.
W
a. The lowest energy (most stable) conformation is staggered
b. The highest energy (least energy) conformation is eclipsed
4. Draw the most stable conformation for each of the following substituted cyclohexanes;
then, in each case, flip the ring and redraw the molecular in the higher energy chair
conformation. Shown all conformation in Newman projections. Fill in hydrogens to
indicate unsubstituted carbons.
a)
b)
most stable conformation:
higher energy conformation:
á
most stable conformation:
higher energy conformation:
3
Da
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 1) Use conformations A andB shown below to answer the following questions. Br. H Br H H H H H CI Conformation A Conformation B Newman projection conformation A a) In the space to the right above, draw a Newman projection looking down the carbon-carbon bond of conformation A. Part of the Newman projection has been drawn for you. b) Which conformation would be more stable (A or B)? c) Which conformation has greater steric strain? (A or B)? d) Circle all the terms that accurately describe conformation A. STAGGERED ECLIPSED GAUCHE ANTI e) Circle all the terms that accurately describe conformation B. STAGGERED ECLIPSED GAUCHE ΑΝΤΙarrow_forward3. Consider the structure below and draw its most stable and least stable conformations in Newman Projections while looking down the bond indicated پر a. The lowest energy (most stable) conformation is Anti. b. The highest energy (least stable) conformation is eclipsed.arrow_forward4. Draw the most stable conformation for each of the following substituted cyclohexanes; then, in each case, flip the ring and redraw the molecular in the higher energy chair conformation. Shown all conformation in Newman projections. Fill in hydrogens to indicate unsubstituted carbons. a) b) most stable conformation: # higher energy conformation: most stable conformation: higher energy conformation: 00 Do poarrow_forward
- ( plz answer in detail , if you hv answered earlier plz skip , do not copy , do all)arrow_forward3. For pentane draw Newman projections for the Syn-periplanar, conformation. the Anti- periplanar conformation and a Gauche conformation. Use C2 as the front carbon and C3 as the back carbon. Label each conformation, circle the highest energy conformation and underline the lowest energy conformation.arrow_forwardConsider the substituted cyclohexane shown in the ball-and-stick model.a. Label the substituents on C1, C2, and C4 as axial or equatorial.b. Are the substituents on C1 and C2 cis or trans to each other?c. Are the substituents on C2 and C4 cis or trans to each other?d. Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forward
- Consider the substituted cyclohexane shown in the ball-and-stick model.a.Label the substituents on C1, C2, and C4 as axial or equatorial. b. Are the substituents on C1 and C2 cis or trans to each other? c.Are the substituents on C2 and C4 cis or trans to each other? d.Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forward1. For the molecules below draw a Newman projection looking down the indicated bond (1⇒2). Your Newman projection needs to be in the same conformation that shown in the structural formula. a) b) view Ph. CI view CI O HN molecule 1 most stable in bond line notation OH 2. a) Provide Newman projects of the three staggered conformations of molecule 1 shown below looking down the indicated bond (1-2). Circle the most stable conformation and draw out the most stable conformation in bond line notation in the box on the left. view least stable in bond line notation b) Provide Newman projects of the three eclipsed conformations of molecule 1 looking down the indicated bond. Put a square around the least stable conformation. and draw out the least stable conformation in bond line notation in the box on the left.arrow_forwardWhat is the relationship (resonance structures, constitutional isomers, conformational isomers, enantiomers, meso compounds, diastereomers, or none of these) between the pair of structures below? 4. а. b. C. CI 5. Circle the most stable conformer of (S)-3,3-dimethyl-2-hexanol. H CH3 CH3 H CH3 (CH2)2CH3 H3C(H2C)2CH3 H3C(H2C)2 CH3 H3C H3C(H2C)2 H3C CH2CH3 CH3 H3C OH H OH H HO, HO CH3 H H,C CH3 ČH2CH3 CH3 6. Circle the compound(s) that is/are optically active (a chiral molecule). (CH2)3CH3 H. HO ČH3 :11 1.arrow_forward
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