ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 4, Problem 4.14P
Problem 4.14 Draw the staggered and eclipsed conformations that result from rotation around the
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Prautice qt#12
For the following compound, draw the appropriate Newman projection along the C1-C2 bond of the
following:
HE
Су
a) The most stable conformer and name the conformer.
b) The least stable conformer and name the conformer.
c) The second most stable conformer and name the conformer.
H
C-Ć- C -CI
Following is the structural formula of 1,2– dichloroethane.
H
H
a) Draw Newman projections for all staggered and eclipsed conformations formed
by rotation from 0° to 360° about the
carbon- carbon single bond.
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 the highest
energy?
CH, CH,
CH
CH, H
CH
H
H
B
C
CH,
CH,
H
H
CH,
D
a) Give the names of conformers, in the order shown. (2)
b) Rank the four conformers in order of stability starting with the LEAST stable, through the MOST stable. (2)
c) State the value of the dihedral angle for each conformer. (2)
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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- Following 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_forwardK Starting from the Newman projection below, rotate the back carbon to provide the structure in the most stable conformation. CI H3C 4 CI CH3 Drawing L Harrow_forwardDraw the most stable conformation of the disubstituted cyclohexane below.arrow_forward
- Starting from the Newman projection below, rotate the back carbon to provide the structure in the least stable conformation. (H3C)₂HC H Q IX H^ H H CH3 oarrow_forwardAdd substituents to draw the conformer below, then rotate the back carbon to provide the structure in the least stable conformation. (H3C) 2HC H -H H CH3 H Draw Newman Projectionarrow_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_forward
- draw a stable conformation of this compoundarrow_forwarda) Draw the two ring flipped conformers of each molecule A and B. Indicate the more stable conformer, respectively. CH3 fCH3 H,C. CH3 H3C. CH3 CI CI A B a) Which is more stable between A and B? Why?arrow_forwardWhich of the following is the highest energy chair conformer of the most stable isomer of 1-ethyl-2,4-dimethylcyclohexane? A | B II C) III IV = || ||| > INarrow_forward
- Question 3 Draw the Newman projection of both highest energy and lowest energy conformations that result from rotation about the C2-C3 bond of 2,3-dimethylbutane.arrow_forwarddraw the newman projection looking down the indicated bond, and then draw the most stable and least stable conformation...arrow_forwardMonosubstituted cyclohexanes occur in two equilibrium conformations. In one conformation, the substituent is in an axial position. In the other conformation, the substituent is in the equatorial position. Complete the drawing of each chair conformation below and circle the more stable conformation. Brarrow_forward
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