Concept explainers
Consider the Newman projection below.
a. Draw a full Lewis structure of this molecule with
b. Given the sizes of these R groups
c. To draw a Newman projection in the lowest P.E. conformation, the following rule of thumbusually applies: Place the largest group on the front carbon anti to the largest group on theback carbon. Is your answer to the previous question consistent with this rule of thumb?
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Organic Chemistry: A Guided Inquiry
- Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This group is called an ethyl group and can be considered a sphere about twice the sizeof a methyl group. Draw the following Newman projections sighting down the C1C2 bond... a. The lowest potential energy conformation. b. The highest potential energy staggered conformation.arrow_forwardUsing your model of butane (CH3CH2CH2CH3) , complete the following graph of the anglebetween the two Me groups vs. potential energy. a. Label each Newman projection of butane on the graph with the words staggered, eclipsed, gauche, and anti, as appropriate. (Note that some structures will have more than one label.) b. Draw a wedge and dash bond representation of butane in its lowest P.E. conformation.arrow_forwardQ2. a) Draw the Newman projection of the most stable staggered conformation of 2-methylpentane, looking down the 3,4 bond. H3C c-CH2-CH2CH3 H3C´H b) The structure of cis-1-tert-butyl-3-methylcyclohexane is shown below. Draw both chair forms of this molecule, and circle the one you think is less stable. Me 't-Buarrow_forward
- 6. Consider the following Newman Projections. Which is the most stable conformation? Which is the least stable? Why? H3CB CH3 CH3 H. H. Br H. CH3 H CH3 CH3 Br H B Carrow_forward. Consider the hash/wedge structure below. a. Draw the Newman projection of the bond indicated, keeping the conformation the same. НО b. Draw the Newman projection for the most stable conformation CI c. In the Newman projection for part b, label all gauche interactions.arrow_forward1. For the molecules below draw a Newman projection looking down the indicated bond (1⇒2). Your Newman projection needs to be in the same conformation that shown in the structural formula. a) b) view Ph. CI view CI O HN molecule 1 most stable in bond line notation OH 2. a) Provide Newman projects of the three staggered conformations of molecule 1 shown below looking down the indicated bond (1-2). Circle the most stable conformation and draw out the most stable conformation in bond line notation in the box on the left. view least stable in bond line notation b) Provide Newman projects of the three eclipsed conformations of molecule 1 looking down the indicated bond. Put a square around the least stable conformation. and draw out the least stable conformation in bond line notation in the box on the left.arrow_forward
- 2. 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_forward6) Which staggered Newman Projection(s), looking down the C2 - C3 bond (C2 in front and C3 in back), illustrates the following boxed compound? OH CH3 H3C H CH3 .H CH=CH2 но. H3C. он но ČH=CH2 H. H3C H. ČH3 ČH=CH2 II III CH3 CH3 CH3 H. CH3 но H. OH ČH=CH2 ČH=CH2 IV Varrow_forward5. Chairs and E2 b. a. Draw the line-bond structure of (1R, 2S,3S)-1-ethyl-2-iodo-3-isopropylcyclohexane. Draw both chair flips of (1R, 2S,3S)-1-ethyl-2-iodo-3-isopropylcyclohexane. Showing all calculations, determine which is the more stable conformation. C. Which chair flip is able to undergo E2 elimination? Justify your answer. d. Show the product of such an E2 elimination using NaOEt as base.arrow_forward
- Q2. Consider the structure shown H₂N G C !!! H₂C I H₂C. HN CH H₂ H₂C 1 CH₂ HN CH H₂ NH,* C=0 C=0 NH₂ CH H₂C HO + HN 11 H₂C N H CH₂ G=0 NH CH NH C=0 CH H₂N. C CH₂ H₂C NH H₂ NH₂ a. Would you consider this a zwitterion or not? Explain. b. If not, would the pH have to increase or decrease to make it a zwitterion? Explain.arrow_forwardConsider rotation about the indicated bond in the molecule below. Which Newman Projection formula best represents the most stable conformer of the molecule with respect to rotation about the indicated bond? [As noted below: there is no steric strain between -H and -Et that have a gauche, staggered relationship] H CH3 Br-C-C-CH₂CH3 H. H Br CH₂CH₂ 1 CH3 H CH3CH₂ H Br H₂C || H H₂C H Br H ||| Select one: OA. I O B. II O C. III O D. All conformers have identical energies. CH₂CH3 H NOTE CH3CH₂ H no steric strainarrow_forward2. For the following structure: (1S, 2R, 4R)-2-chloro-1-isopropyl-4-methylcyclohexane a. draw both chair conformations for the molecule b. identify whether the more stable stereoisomer.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning