
Interpretation:
The observation that the N,N,N-trimethylammonium group –N(CH3)3, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.
Concept introduction:
In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.
If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.
The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.
To explain:
The observation that the N,N,N-trimethylammonium group –N(CH3)3, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

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Chapter 16 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
- (a) Sketch the 'H NMR of the following chemical including the approximate chemical shifts, the multiplicity (splitting) of all signals and the integration (b) How many signals would you expect in the 13C NMR? CH3arrow_forwardDraw the Show the major and minor product(s) for the following reaction mechanisms for both reactions and show all resonance structures for any Explain why the major product is favoured? intermediates H-Brarrow_forwardChoose the right answerarrow_forward
- 8. What is the major product of the following reaction? KMnO4 b a TOH OH OH C d OH "OH HO OH OHarrow_forwardChoose the right answerarrow_forward3. Draw ALL THE POSSBILE PRODUCTS AND THE MECHANISMS WITH ALL RESONANCE STRUCTURES. Explain using the resonance structures why the major product(s) are formed over the minor product(s). H₂SO4, HONO CHarrow_forward
- 7. Provide the product(s), starting material(s) and/or condition(s) required for the No mechanisms required. below reaction HO + H-I CI FO Br2, FeBr3 O I-Oarrow_forward6. Design the most efficient synthesis of the following product starting from phenot Provide the reaction conditions for each step (more than one step is required) and explain the selectivity of each reaction. NO MECHANISMS ARE REQUIRED. OH step(s) CIarrow_forwardWhat is the skeletal structure of the product of the following organic reaction?arrow_forward
- If a reaction occurs, what would be the major products? Please include a detailed explanation as well as a drawing showing how the reaction occurs and what the final product is.arrow_forwardWhat is the major organic product of the following nucleophilic acyl substitution reaction of an acid chloride below?arrow_forwardWould the following organic synthesis occur in one step? Add any missing products, required catalysts, inorganic reagents, and other important conditions. Please include a detailed explanation and drawings showing how the reaction may occur in one step.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

