Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 4.9, Problem 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 (6th Edition)
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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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
- 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_forwardStarting 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_forward
- a) 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_forwardDraw the Newman projection so that it corresponds to the molecule and conformation shown when viewed down the red bond in the direction of the arrow. H I H CH3 X 5 Carrow_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
- Draw the most stable conformation of trans-1,2-dimethylcyclohexanearrow_forwardQuestion 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 so that it corresponds to the molecule and conformation shown when viewed down the red bond in the direction of the arrow. Cl X H₂C H HS SHarrow_forward
- Question 3 CH3 a) Draw the chair conformations of the four cis-trans isomers of menthol (see structure on the right) b) Which is the most stable conformation? Explain your OH, answer. H3C CH3arrow_forwardGiven the structures of the following two tetramethylcyclohexanes: CH3 CH3 H3C" CH3 H3C" CH3 CH3 CH3 A B (a) Draw the most stable chair conformation for both A and B. Which structure is lower in energy (most stable)? (b) Ring flip the above structures and draw the least stable chair conformation for both A and B. Which structure is highest in energy (least stable)?arrow_forward190x3 3.1.2 The conformations of cycloalkanes Construct a model of cyclohexane (C6H12), a six-membered ring of carbon atoms with two hydrogen atoms attached to each carbon atom. Is the ring planar or puckered? 1. (a) 55 (b) The cyclohexane ring can be arranged in many forms. The two major forms are commonly called the chair conformation and the boat conformation. For instance in the chair conformation; consider the two hydrogen atoms at each carbon. One C-H bond is roughly in the mean plane of the molecule and one C-H bond is roughly perpendicular to that plane. These two positions are referred to, respectively, as equatorial and axial, as shown below. axial bond H equatorial bond Hequatorial H axial H wallon (i) Arrange the model in the chair form. Clearly add and label the axial (a) and equatorial (e) hydrogens on the sketch of the chair confirmation below. emend bundano (c) Arrange the model in the boat form. Clearly add and label the axial (a) and equatorial (e) hydrogens on the…arrow_forward
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