Concept explainers
(a)
Interpretation: The given molecules need to be labeled as cis, trans or neither. The type of position of H atom circled in the given diagram needs to be described.
Concept Introduction: Chair conformation is the most stable conformation of cyclohexane. It is represented as follows:
Here, the substituted groups in the chair conformation are represented as follows:
The groups showing in straight upward and downward directions are axial and the groups bend slightly right or left are equatorial.
(b)
Interpretation: The picture of the molecule needs to be drawn after the chair flip.
Concept Introduction:
The chair conformation of cyclohexane is represented as follows:
During the flipping, no bond is break. The numbering in the chair form is represented as follows:
During ring flipping, mirror image of the chair conformation is formed.
It is represented as follows:
(c)
Interpretation: In each of the molecule of part (b), the conformation needs to be circled which is lower in potential energy.
Concept Introduction: The molecule with lowest potential energy is most stable. In the chair conformation of the cyclohexane, the stable conformation is when large groups are present in the equatorial positions. The equatorial positions in the chair conformation points away from the ring thus, there is more space.
(d)
Interpretation: The name of the two molecules drawn in part (b) needs to be determined
Concept Introduction: Chair conformation is the most stable conformation of cyclohexane. It is represented as follows:
Here, the substituted groups in the chair conformation are represented as follows:
The groups showing in straight upward and downward directions are axial and the groups bend slightly right or left are equatorial.
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Organic Chemistry: A Guided Inquiry
- Consider 1,2-dimethylcyclohexane.a. Draw structures for the cis and trans isomers using a hexagon for the six-membered ring.b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?d. Which isomer, cis or trans, is more stable and why?arrow_forward7. 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 HOarrow_forwardShown below is Streptomycin, and Neomycin B. Circle and label as many functional groups in these molecules as you can. a. Label each chiral carbon in Streptomycin. How many total stereoisomers exist for Streptomycin? b. Label each chiral carbon in Neomycin B. How many total stereoisomers exist for Neomycin B?arrow_forward
- OH a. Draw the cis and trans isomer of the molecule above. b. Draw the chair form of the trans isomer of the molecule. C. Draw the flipped chair form of the trans isomer of the molecule. d. What is the more stable chair form?arrow_forward3. Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and the equatorial hydrogens (He).arrow_forwardHow 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_forward
- 4. For the following structures, draw both possible chair conformations, using a ring flip to go from one to the other, and circle the one that is most stable/lowest energy. (Hint: Use Table 4.8 in Klein.) Show all groups, including hydrogen atoms, attached to the cyclohexane ring. А. Me Me Et В. Et t-Bu Etarrow_forward3. Draw a ring-flip isomer for the following compounds and circle the most stable conformation.arrow_forwardDetermine whether each Newman projection is in the staggered or eclipsed conformation. Choose.. CH3 H. H. Choose... - CI CH3 H. Choose..- CH3 H. H. Choose.. CI CH3 ( BACK Question 5 of 7 archarrow_forward
- Consider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d.Which isomer, cis or trans, is more stable and why?arrow_forwardDraw the most stable conformer of the following compounds, using Newman projections.arrow_forwarda. Draw the structure of this molecule as a hexagon with dash(es) and/or wedge(s). ha -OH b. Draw the other chair conformation. c. Draw the enantiomer of the molecule in its most stable conformation. он H d. Ignoring differences in conformation, how is this molecule related to the one above? Are they the Same molecule, Enantiomers, or Diastereomers? OH H₂ HH₂ POM (CH₂)2arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning