Concept explainers
(a)
Interpretation:
Why the greater contribution, from the second of the two resonance structures shown, is counterintuitive based on charge stability is to be explained.
Concept introduction:
The relative stabilities of resonance structures can be determined on the basis of charge stability. The structure with positive charge on less electronegative atom and negative charge on more electronegative atom is more stable. The most stable resonance structure contributes more to the resonance hybrid.
(b)
Interpretation:
The greater contribution from the second resonance structure is to be explained.
Concept introduction:
The most stable resonance structure contributes most to the hybrid.
Stability of a resonance structure depends on a number of factors. More the number of bonds, more the number of atoms that follow the octet or the duet rule and less the number of formal charge, the more stable the structure.
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- (a) Draw all valid resonance contributors for this iIon. Show how the electrons can be moved using curved arrOWs. (b) Draw the resonance hybrid.arrow_forwardProblem Which of the following substances exhibits H bonding? For any that do, show the H bonds between two of its molecules. (a) C̟H, (b) CH;OH (c) CH3C–NH,arrow_forward3) Draw two more resonance structures of the following compound. Order the structures by increasing stability.arrow_forward
- 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_forwardPlease guide me on how to draw the best resonance structure, thank you.arrow_forwardProblem What amount (mol) of each ion is in each solution?(a) 5.0 mol of ammonium sulfate dissolved in water(b) 78.5 g of cesium bromide dissolved in water(c) 7.42×1022 formula units of copper(II) nitrate dissolved in water(d) 35 mL of 0.84 M zinc chloridePlan We write an equation that shows 1 mol of compound dissociating into ions. (a) We multiply the number of moles of ions by 5.0. (b) We first convert grams to moles. (c) We first convert formula units to moles. (d) We first convert molarity and volume to moles.arrow_forward
- 3) Enols are an important class of molecules in organic chemistry, which are utilized for theirability to form carbon-carbon bonds. We will learn about their unique reactivity much later inthe course. Shown below is an enol on the left, whereas the molecule on the right is classifiedas an allylic alcohol. a) Please explain why the structure on the right IS NOT a resonance structure of the enol on theleft. A short statement or illustration is fine, be sure that your rationale is clear. b) Draw the correct resonance structure that can be produced from the enol on the left. Besure to include arrows to indicate the movement of electrons in the left-hand structure andindicate charges in the resulting structure. c) What is the hybridization of the carbon indicated with the red arrow?arrow_forwardProblem (#2.) For each ion below, draw all reasonable resonance structures (linked by resonance arrows “↔”). Include curved arrows that indicate the movement of electrons between each resonance structure. Assign non-zero formal charges to each atom for each resonance structure. (a.) NO3– (nitrate) (b.) CH3COO– (acetate) (c.) N3– (azide) (d.) NCO– (isocyanate) Problem (#3.) For each ion in question 2, draw a resonance hybrid, assigning non-zero formal and/or partial charges (δ+, δ–) as needed. Problem (#4.) For each skeletal structure below, satisfy the valences (or octets) of all of the atoms by filling in double and triple bonds as well as unshared electron pairs. Assign non-zero formal charges and show the overall charge if the structure is an ion. See photo attached for Problem number 4. Problem (#5.) For each structure in question 4, draw a resonance hybrid (if it has one) and assign non-zero formal and/or partial charges as needed.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_forward
- Explain with the help of resonance structures which of the two nitrogen atoms is more basic in the following molecule.arrow_forwardFuran, shown below, exhibit resonance stabilization. Which of the following is an INVALID resonance structure of furan?arrow_forwardPlease provide me explanations, or draw the resonance structure to explain.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning