Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Question
Chapter 4, Problem 4.57P
Interpretation Introduction
(a)
Interpretation: The orientation of
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
Interpretation Introduction
(b)
Interpretation: The location of substituent on
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
Interpretation Introduction
(c)
Interpretation: The orientation of an equatorial
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
Interpretation Introduction
(d)
Interpretation: The orientation of substituent
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
Interpretation Introduction
(e)
Interpretation: The location of substituent on
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
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Students have asked these similar questions
Which statement is true about these conformers?
H.
H.
H H
CH3
H3C
H.
H,C
H,C
H.
H.
A
O A and B are equally stable
O Difficult to predict
O A more stable than B
) B more stable than
5a. Draw a Newman Projection for the following compound.
5b. Rotation about the C3 – C4 bond in conformer 1 leads to two less stable staggered conformers. Draw a Newman Projection for one of these less stable conformers, as viewed down the C3 to C4 bond. What is the single highest energy gauche interaction in the Newman Projection?
Part D. Do the two structures A and B of each pair drawn below represent the same molecule,
constitutional isomers, or stereoisomers? If A and B are stereoisomers, further classify them as
enantiomers or diastereomers.
H3C
Structure A
H3C
HO
H3C
H3C
Br
T
H
H3C
H
HO
H3CC
H
C
Br
HC
H
H
H
H
CH₂Br
CH₂CH3
H
CH₂CH3
CH₂OH
OH
H HO
G
G
H HO
H HO
G
CH3
CH3
CH3
Br
Hallo
H
H3C
H
Structure B
H3C
CH3
Br
WING
H
Br
HOCH₂
CH3
CH3
HO
H
CH₂OH
H
CH₂CH3
H
CH₂CH3
H
H
H
H
H
H
Gim
CH3 H
OH
"H
·GII.
CH3
HO.
OH
OH
CH3
CH3
OH
Relationship of A and B
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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- Is 2-methyl-prop-1-ene symmetric? Please explain why with emphasis on the hybridization of each carbon in the C-C double bond.arrow_forwardCYCLOHEXANE 2D REPRESENTATION Cyclohexane Chair by stereoaisier H H H. „CH2. H CH H. H H V STAGGERED O ECLIPSED O 1,3-DIAXIAL INTERACTION CHAIR BOAT CHAIR In which conformation are the hydrogen atoms farthest apart? Which is the preferred conformation? Give reasons for your answer. Which is the eclipsed conformation?arrow_forward5. Select the most stable conformer of cis-1, 3- cyclohexane diol. HO OH OH OH НО. OH Брон OH OH B D A) A B) B C) C D) DE) E OHarrow_forward
- How many chirality centers exist on this molecule? What is the absolute configuration of the primary alcohol in this structure? How many lone pairs are on the structure? How many sp2 hybridized atoms are on the structure?arrow_forwardAnswer the following questions about compound A, which contains a CH3 group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown a.) Are the CH3 and OH groups oriented cis or trans to each other?b.) Is a substituent on Ca that is cis to the CH3 group located in the axial or equatorial position? c.) Is an equatorial Br at Cb oriented cis or trans to the OH group?d.) Is the H atom on Cc located cis or trans to the OH group?e.) Is a substituent on Cd that is trans to the OH group located in the axial or equatorial position?arrow_forward8. Circle the descriptor that most accurately characterizes the relationship between the two molecules represented below. Assume there is free rotation about single bonds. CH3 H diastereomers CI Br Br enantiomers CI non-isomers / identical structures constitutional isomers non-isomers / different structures atropisomers geometric isomers H -H CH3 H H3C CH3arrow_forward
- Draw all six ketone constitutional isomers of the formula C6H12O Follow the instructions and draw the five different possible arrangements of six carbon units. For parts A-C, draw only the six carbon atoms and Do Not draw the ketone. A:draw the structure containing six carbons in the longest parent chain. B: draw the two structures containing five carbons in the longest parent chain. C: Draw the two structures containing four carbons in the longest parent chain. D: Using the five structures from parts A,B,&C as a guide, draw the skeletal structures of the six constitutional isomers of C6H12O that are ketones.arrow_forwardA CH3 *** CH3 E 6 74 CH3 trans trans Cis Cis 4. Draw a constitutional isomer and a stereoisomer of the compound below. CH₂ A CH3arrow_forwardFor 1,2-dichloroethane: a.Draw Newman projections for all eclipsed conformations formed by rotation from 0° to 360° about the carbon-carbon single bond. b.Which eclipsed conformation(s) has (have) the lowest energy? Which has (have) the highest energy? c.Which, if any, of these eclipsed conformations are related by reflection?arrow_forward
- 19. Refer to the molecule below. (1) Draw the newman projection for carbon #1 and #2. Let the carbon #1 containing the methyl group to be at the front while carbon #2 containing the methyl and ethyl group to be at the back of the newman projection. (2) Rotate the carbon #1 to 60 degree for 6 times until a 360 degree rotation was achieved. (3) Encircle the MOST UNSTABLE conformation. 4 3arrow_forwardAnswer the following questions and upload your answer. A. Draw the two chair conformations of cis-1-isopropyl-3-methylcyclohexane. Write under your drawing which conformation is the most stable one. B. Would the trans isomer be more stable than the cis isomer? Why?arrow_forward2) In the space below, draw all of the stereoisomers of molecule a. a) CH 3 H-C-F H-C-F F-C-H CH3arrow_forward
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