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Interpretation:
Second resonance contributor for each of the given structures is to be written. Whether the charge or unpaired electron is shared equally by both allylic carbons or not is to be determined. If the charge or unpaired electron is not shared equally, the carbon atom which bears more charge or unpaired electron is to be identified.
Concept Introduction:
>The carbon atom which is adjacent to either of the double bonded carbon atoms is the allylic carbon atom. An allylic carbon atom is
The allylic unit can be positively charged carbocation
Each of the above stabilizes by delocalization involving pi electrons in the double bond.
>The positive charge, negative charge, or unpaired electron is shared by the two carbons at the opposite ends of the allyl group.
>In allylic species that are not symmetrically substituted, the two resonance structures are not equivalent and do not contribute equally to the resonance hybrid.
>The most stable resonance structure contributes more to the resonance hybrid.
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Chapter 11 Solutions
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
- Draw all resonance contributors for each of the following molecules or ions. Be sure to include the curved arrows thatindicate which pairs of electrons are shifted in going from one resonance structure to the next.(a) CH3NO2(b) CH3CO-2(c) CH3CHCHCH-2(the ion has two C-C single bonds)(d) C5H5N (a ring is formed by the C and N atoms, and each H is bonded to C)(e) C4H5N (a ring is formed by the C and N atoms, the N is bonded to one H, and each C is bonded to one H)arrow_forwardThe two species shown are structurally very similar. Draw all resonance structures for each species and determine which (a or b) is more stable. Explain. (a) (b)arrow_forward6) For each of the following, draw a representation explicitly showing all atoms. Denote the partia charge on each atom (including implied hydrogens) and rank the atoms from most negative to most positive. a) Potassium hydroxide KOH gativ is to have on reactivity? b) Potassium tert-butoxide KOtBu c) Which of these two structures will bear a greater negative charge on the oxygen atom? Explain. d) Considering your answer to part C, which of the two species do you expect to be a stronge base? Explain your reasoning.arrow_forward
- (b) Distinguish each as aromatic or antiaromatic in terms of electronic basis. Explain which one is more stable. (i) Compound A Compound B (ii) Compound C Compound D (iii) Compound E Compound Farrow_forwardIndetify the molecule that is (2S,3R)-3-chloro-2-methylbutan-1,2-ol. (A, B, C or D)arrow_forwardClassify each of the following compounds as aromatic, anti-aromatic, or non-aromatic. Assume all rings are planar (Please explain)arrow_forward
- (a) Draw an energy diagram for the cyclopropenyl MOs. (The polygon rule is helpful.) Label each MO as bonding, nonbonding, or antibonding, and add the nonbonding line. Notice that it goes through the approximate average of the MOs.(b) Add electrons to your energy diagram to show the configuration of the cyclopropenyl cation and the cyclopropenyl anion. Which is aromatic and which is antiaromatic?arrow_forwardSee the Attachment & solev the followings (a) Add curved arrows to show how the starting material A is convertedto the product B. (b) Draw all reasonable resonance structures for B. (c) Draw the resonance hybrid for B.arrow_forwardResveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inflammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.arrow_forward
- Classify the following resonance structures (a) - (c) as MOST, MAJOR and MINOR Contributor.arrow_forwardwhy is the first compound (E) while the second compound is (Z)arrow_forwardThe central carbon atom of an allene is a member of two double bonds, and ithas an interesting orbital arrangement that holds the two ends of the molecule at rightangles to each other.(a) Draw an orbital diagram of allene, showing why the two ends are perpendicular.arrow_forward
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