ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Chapter 4.9, Problem 15P
Interpretation Introduction
Interpretation: The possible Newman projections for
Concept introduction: Newman projections are drawn to visualize the different conformations of a compound around
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organic chemistry
Hydrocarbon X below has the following Newman projection. Which of the
following corresponds to Hydrocarbon X?
O 2,3-dimethylhexane
O 2,4-dimethylpentane
O 2,4-dimethylhexane
O 2,3-dimethylpentane
O n-heptane
H3C
a DH
H
CH3
CH₂CH3
H3C
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?
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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- Draw a dash-wedge structure for (1R)-1-bromo-1,3,3-trimethylcyclohexane.arrow_forward4. (a) Draw a skeletal (line-bond) structure for 3,4-dimethylhexane. (b) Draw a sawhorse representation of any staggered conformation of this molecule looking down the carbon-3 to carbon-4 bond. (c) Draw a Newman projection looking down the carbon-3 to carbon-4 bond of the same conformation that you drew as a sawhorse representation.arrow_forward. Draw the two most stable Newman projections of 3-methylpentane by viewing along the C2-C3 bond.arrow_forward
- 3. Draw Newman projection for the highest and lowest energy conformers of your assigned molecule. Provide a rationale to support your answer. In other words, why is the highest energy conformer so high in energy? Why is the lowest energy conformer low in energy? Molecule (2R,3S)-2-Bromo-3- Floro butanearrow_forwardDraw the highest and lowest energy Newman projection for 2- bromo-2,3-dimethylpentane when looking down C1-C2, C2-C3, C3-C4, C4-C5 bonds.arrow_forwardFollowing 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_forward
- What structure has the lowest energy?arrow_forwardSighting down the Ci-C2 bond axis of 1-bromopentane, Br-CH2-CH2CH2CH»CH3, draw the Newman projection of a) the anti staggered conformation b) the gauche staggered conformation c) the two eclipsed conformations. Which eclipsed structure would you expect to have the highest strain energy?arrow_forward2. Convert the following bond-line structure to Newman projections that represents it lowest energy and highest energy conformations. Look down the indicated C2-C3 bond. lowest energy highest energyarrow_forward
- Ff.154.arrow_forward2. Use the Newman projection to identify the structure shown: (a) as a Fischer projection (b) as a bond-line structure (c) by name Circle your answer for each part. CH2CH3 F+ H CH(CH3)2 CH2CH3 H+ F CH(CH3)2 三F H CH2CH3 H H F no CH(CH3)2 geslaan sam o Y (S)-4-fluoro-2-methylhexane F (R)-4-fluoro-2-methylhexanearrow_forwardBuild a model of methylcyclohexane, and use the model to complete the following Newmanprojections of methylcyclohexane in the chair conformation: a. When the methyl group is in an axial or equatorial (circle one) position, the molecule is inits lowest potential energy conformation. b. Label one Newman projection above anti and the other gauche to describe the relationshipbetween the methyl group and C3 of the ring. c. In general, which is a lower PE conformation, anti or gauche? d. Explain how your answer to b and c provide an explanation for why it is more favorable fora large group to be in an equatorial than an axial position.arrow_forward
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