EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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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?
1E.) Which of the following two conformers is lower in energy?
Both conformers are
of equal enery
O
A
Conformer A is lower
in energy.
B
Conformer B is lower
in energy.
It cannot be
determined
a.
b.
For the following two pairs of molecules,
(1) Draw out the chair conformation for each molecule, flip the ring if it is possible.
(2) Compare both molecules to circle out which one is more stable.
(3) Identify their relationship as: constitutional isomer, conformational isomer,
stereoisomer or identical.
(4) Find all the chiral center on each molecule and label them.
Br
and
ZX-
and
VS.
H
H
H
Br
H
H
∞
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Similar questions
- Following is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?arrow_forwardQ2: Drawn are four isomeric dimethylcyclopropanes. a. How are the compounds in each pair related (enantiomers, diastereomers, constitutional isomers): A and 8; A and C; B and C, Cand D? b. Label each compound as chiral or achiral. c. Which compounds, alone, would be optically active? d. Which compounds have a plane of symmetry? e. Which of the compounds are meso compounds? f. Would an equal mixture of compounds C and D be optically active? What about an equal mixture of B and C?arrow_forward4. Draw the most stable chair conformation of the following disubstituted cyclohexane. Draw carefully positioned intersecting arcs to denote all sources of steric strain for this conformation. CH3 CH3arrow_forward
- 2. H3CO H3CO HO 1. Consider the molecule shown below. [1] Draw the two chair conformations for the compound. [2] Identify which of the two chair conformations is more stable and explain why. H3CO Jonoto NH₂ How are the following molecules related? (exactly the same, completely different, constitutional isomers, enantiomers, or diastereomers). OH OH OCH3 HO“ OH H3CO H3CO is content is protected and may not be shared, uploaded of ributed OCH3 HO,,, OH O... "OCH3arrow_forwardQ5. Estimate AG (free-energy difference being positive or negative; equilibrium direction) between the stable and unstable chair conformations of the following tri-substituted cyclohexanes and explain your reasoning. CH3 OH OH CH3 OH CH3 F OH CH3 F OHarrow_forwardFor each compound drawn below: a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashes for substituents. 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? [1] [2] [3]arrow_forward
- 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 Barrow_forwardDraw Newman Projections of the following molecule, looking down the C2-C3 bond. Under A, draw the anti conformation, under B, draw a Gauche conformation, under C, draw the least stable eclipsed conformation. A B Carrow_forwardDraw each compound in its most stable conformation(s). Then draw it in its most symmetric conformation, and determine whether it is chiral. trans-1,2-dibromocyclohexanearrow_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_forwardHow many tetrahedral stereogenic centers does PGF2a contain? Draw its enantiomer. How many of its double bonds can exhibit cis-trans isomerism? Considering both its double bonds and its tetrahedral stereogenic centers, how many stereoisomers are possible for PGF2a?arrow_forwarda. Draw the two chair conformers for each of the stereoisomers of trans-1-tert-butyl-3-methylcyclohexane. b. For each pair, indicate which conformer is more stable.arrow_forward
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