Custom eBook for Organic Chemistry
2nd Edition
ISBN: 9798214171104
Author: Straumanis
Publisher: Cengage Custom
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Question
Chapter 7, Problem 8CTQ
(a)
Interpretation Introduction
Interpretation:
The relationship of given compound with the compound in Figure 7.3 should be stated.
Concept Introduction:
The compounds that have same molecular formula but have different arrangement of atoms in a space are known as isomers.
Conformers are obtained by the interconvertion of a molecule without breaking the bond through the rotation about a single bond. Consitutional isomers have same molecule formula but have different connectivity of atoms. The compounds that have same molecular formula and also have the connectivity of atoms but cannot be converted into one another by rotation about a single bond are known as configuratiol stereoisomers.
(b)
Interpretation Introduction
Interpretation:
The purpose behind to dermine the name of each molecule before to identify reactionship of each molecule with cis-1,2-dimethylcyclohexane should be predicted.
Concept Introduction:
The compounds that have same molecular formula but have different arrangement of atoms in a space are known as isomers.
Conformers are obtained by the interconvertion of a molecule without breaking the bond through the rotation about a single bond. Consitutional isomers have same molecule formula but have different connectivity of atoms. The compounds that have same molecular formula and also have the connectivity of atoms but cannot be converted into one another by rotation about a single bond are known as configuratiol stereoisomers.
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a. For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. ( see image)
b.Draw and name the seven constitutional isomers (all contain a ring of some size) for cycloalkane, C6H12.
7. Draw curved arrows indicating the movements of electrons between the following pair of
resonance structures. Name the pattern of resonance shown. What is the hybridization of the
carbon atoms?
8. Draw the remaining three resonance structures for the molecule in problem 7 above.
9. There are several possible forms of a trisubstituted cyclohexane with the formula C10H200. I
have drawn four of them. From these, which one do you think is most commonly naturally
occurring, and why? Which is least commonly occurring and why?
HO
HO"
HO
HO
Sight along the C2-Cl bond of 2-methylpropane (isobutane).
a. Draw a Newman projection of the most stable conformation.
b. Draw a Newman projection of the least stable conformation.
c. Make a graph of energy versus angle of rotation around the C2-Cl bond.
d. Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.
Chapter 7 Solutions
Custom eBook for Organic Chemistry
Ch. 7 - Prob. 1CTQCh. 7 - Prob. 2CTQCh. 7 - Prob. 3CTQCh. 7 - Draw wedge and dash skeletal representations of...Ch. 7 - Label each ring in Figure 7.2 cis or trans.Ch. 7 - Prob. 6CTQCh. 7 - Prob. 7CTQCh. 7 - Prob. 8CTQCh. 7 - a model of cyclohexane in a chair conformation,...Ch. 7 - Prob. 10CTQ
Ch. 7 - Prob. 11CTQCh. 7 - Fill in the blanks: cis-1,3-Dimethylcyclohexane...Ch. 7 - Prob. 13CTQCh. 7 - Prob. 14CTQCh. 7 - Prob. 15CTQCh. 7 - Prob. 16CTQCh. 7 - Prob. 17CTQCh. 7 - Prob. 18CTQCh. 7 - Draw chair representations of...Ch. 7 - Which stereoisomer in the previous question is...Ch. 7 - Prob. 21CTQCh. 7 - Prob. 1ECh. 7 - Label each of the following as cis, trans or...Ch. 7 - Which pair has more in common with one another?Ch. 7 - Prob. 4ECh. 7 - Prob. 5ECh. 7 - Prob. 6ECh. 7 - Fill in the table by drawing a representation of a...Ch. 7 - Prob. 9ECh. 7 - True or False: If you perform a chair flip on...Ch. 7 - Prob. 11ECh. 7 - Prob. 12ECh. 7 - Prob. 13ECh. 7 - Prob. 14ECh. 7 - Prob. 15ECh. 7 - Draw trans-1-tert-butyl-3-methylcyclohexane in its...Ch. 7 - Build a model of methylcyclohexane, and use the...
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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
- 9) There are 3 different cyclopropane molecules with the formula GHĄC12. a. Draw and build the 3 molecules. b. Below each drawing, name each molecule with correct nomenclature. Label a pair that are constitutional isomers. d. Label a pair that are stereoisomers (or configurational isomers). С.arrow_forward6. Use the molecule below to answer the following questions. a) Name the following molecule. b) Why is it necessary to provide R or S designation in order to clearly communicate molecular structure for this molecule? c) How many stereoisomers of this molecule are possible? Which of them are enantiomers to each other? Which are diastereomers? SH ICNarrow_forwarda. Draw the lowest energy conformation for the compound shown in the image. b. Draw the complete structural formula of the following compound: cis-1-bromo-3-chlorocyclohexane.arrow_forward
- Answer 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_forward3. Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and the equatorial hydrogens (He).arrow_forwardReplace one of the H atoms in the ethane model with a Br atom, to form ethyl bromide CH3CH2Br, and draw a projection (lewis) and a perspective drawing. Does replacing different hydrogen atoms in CH3CH3 to produce Ch3CH2br give you different isomers? (i.e. Are all the hydrogen atoms equivalent?) How many isomers of CH3CH2Br can you construct? Make a model of one other conformer of CH3CH2Br. DId you need to break any bonds to form the second conformer from the first?arrow_forward
- 1: Draw the chain conformer of... 1a. Cyclohexane, label all the axial and equatorial hydrogens 1b. The most stable conformer of ethylcyclohexane 1c. The most sable conformer of trans-1-tert-butyl-3-methylcyclohexanearrow_forward5. Construct models of all the stereoisomers of 1-bromopropene. Draw the line structure of your models. Are these molecules isomers? If they are isomers to what specific category do they belong? Assign E or Z descriptors to each compound, if appropriate. 6. Construct a model of dibromochloromethane and draw the perspective structure. How many planes of symmetry does this molecule possess? Construct the mirror image of your model. Are the two models superimposable? Classify or describe the relationship between these two mirror images, and assign R or S descriptors, if appropriate.arrow_forwardModel 2. Cyclohexane Chair Conformation Another helpful way to drawn a non-planar example of cyclohexane is to draw its most stable (lowest energy) conformation called a chair conformation. III 8. Build two models of cyclohexane. The chair conformation is the most stable conformation of cyclohexane because all of the bond angles around the carbon atoms are at 109.5ª and all carbon atoms are in the more stable staggered conformation. Cyclohexane is the only cyclic structure that allows all the bond angles around each carbon to be 109.5", thus is the only ring that adopts a true chair conformation. Form the chair conformation with both of your cyclohexane models. Look down each carbon carbon bond and verify that all carbons are in a staggered conformation. 9. 10. Because of this conformation, there are two types of positions a group can occupy when it is attached to a cyclohexane chair, either axial (A) or equatorial (E). 11. Axial hydrogens alternate straight up and straight down as we…arrow_forward
- How are the molecules below related to each other? (Hint: convert each to a partially condensed structual formula). Н. H H CH3 H₂C CH3 CH3 and H H H H₂c-CH₂ CH3 H CH3 Select one: OA. They are constitutional isomers. OB. They are identical compounds. O C. They are geometrical isomers. O D. They are stereoisomers. O E. They are different compounds, not isomers..arrow_forward1,2-ditert-butylcyclohexane is an interesting case of a conformational study. The cis isomer is more stable than the trans isomer, although the trans isomer presents a conformer with both substituents in equatorial positions. In order to analyze this fact:a. Draw the conformational equilibrium of both compounds. Explain using and drawing the structures why this difference happens (the one described above). b. In the trans isomer, the di-axial conformation is 25.9 kJ / mol more stable than the di-equatorial. Calculate the energy of the di-equatorial conformation.arrow_forwardFor each structure below: i. Write a condensed formula (e.g. ethanol would be CH3CH2OH) ii. Write the hybridization (sp, sp2, or sp3) of each C, N, and O. iii. Identify all functional groups present. (Note: only choose alkane if that is the only functional group present.) iv. Count the number of degrees of unsaturation. N' HO, For each formula below: i. Calculate the degrees of unsaturation. ii. Draw at least two different constitutional isomers, iii. Name all functional groups in each structure that you draw. a. C3HSO b. CAH&O c. CaH,N d. CH6O2arrow_forward
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