Resonance structures drawing

The situation is more complicated when the set of reasonable contributing structures are not all equivalent. Examine the geometry and atomic charges forphenoxide anion. Do these data fit any one of the possible resonance structures (draw all reasonable possibilities), or is a combination of two or more resonance contributors necessary ... 

The following ions are best described with resonance structures. Draw the resonance structures, and using formal charge arguments, predict the best Lewis structure for each ion. 

Consider the compounds and ions with curved arrows drawn below. When the curved arrows give a second valid resonance structure, draw the resonance structure. When the curved arrows generate an invalid Lewis structure, explain why the structure is unacceptable. 

The regioselectivity of the gas-phase protonation of phenol can be understood in simple terms of its resonance structures. Drawing them, we may figure out that a positive r-charge of the protonated form is mainly localized in the para- and ortfio-positions with respect to the protonation site. If the OH group is attached to one of these positions, the relevant molecule is then described by four resonance structures, resulting in the positive r-charge... 

Analyze and Conclude One of the molecules from this lab undergoes resonance. Identify the molecule that has three resonance structures, draw the structures, and explain why resonance occurs. 

NO2 includes two resonance structures. Draw these structures (include formal charges). What is the N-0 bond order ... 

Think About It The Lewis structure given for thalidomide is one of two possible resonance structures. Draw the other resonance structure, and count sigma and pi bonds again. Make sure you get the same answer. 

Practice Problem B Given the following two resonance structures, draw the curved arrows on the first structure that will give rise to the second structure. 

Draw all possible resonance structures for creatine phosphate and discuss their possible effects on resonance stabilization of the molecule. 

Draw resonance structures for the possible radicals resulting from hydrogen atom abstraction from toluene. Which would you anticipate to be the most stable Why Compare energies for the different radicals (radical A, radical B,. ..). Is the lowest-energy radical that which you anticipated Are any of the alternatives significantly better than any of the others Explain your reasoning. 

Just as there is a C=0 bond to the left of the lone pair, there is a second C=0 bond to the right. Thus, we can draw a total of three resonance structures for the 2,4-pentanedione anion. 

A Draw as many resonance structures as you can for the following species ... 

Phenol, C6H5OH, is a stronger acid than methanol, CH3OH, even though both contain an O-H bond. Draw the structures of the anions resulting from loss of H+ from phenol and methanol, and use resonance structures to explain the difference in acidity. 

Draw resonance structures for the benzyl radical, C6H5CH2-, the intermediate produced in the NBS bromination reaction of toluene (Problem 10.27). 

Problem 15.6 Draw the five resonance structures of the cyclopentadienyl anion. Are all carbon-carbon bonds equivalent How many absorption lines would you expect to see in the lH NMR and, 3C NMR spectra of the anion ... 

The following molecular model is thatof a carbocation. Draw two resonance structures for the carbocation, indicating the positions of the double bonds. 

There are four resonance structures for anthracene, one of which is shown. Draw the other three. 

There are five resonance structures of phenanthrene, one of winch is shown. Draw the other four. 

Problem 16.14 Draw resonance structures for the intermediates from reaction of an electrophile at the ortho, meta, and para positions of nitrobenzene. Which intermediates are most stable ... 

The nitroso group, — N = Op is one of the few nonhalogens that is an ortho- and para-directing deactivator. Explain by drawing resonance structures of the carbocation intermediates in ortho, mela, and para electrophilic reaction on nitrosobenzene, C<3Hs N = 0. 

At what position, and on what ring, would you expect bromination of benz-anilide to occur Explain by drawing resonance structures of the intennediates. 

Draw resonance structures of the intermediate carbocations in the bromillation of naphthalene, and account for the fact that naphthalene undergoes electrophilic substitution at Cl rather than C2. 

You knowr the mechanism of HBr addition to alkenes, and you know the effects of various substituent groups on aromatic substitution. Use this knowledge to predict which of the following two alkenes reacts faster with HBr. Explain your answer by drawing resonance structures of the carbocation intermediates. 

Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring has a large effect. The pKa of unsubstituted phenol, for example, is 9.89, while that of p-nitrophenol is 7.15, Draw resonance structures of the corresponding phenoxide anions and explain the data. 

Draw a resonance structure of the acetonitrile anion, - CH2C=K, and account for the acidity of nitriles. 

Account for the fact that p-nitroaniline (pKa = 1.0) is less basic than m-nitroaniline (pKa = 2.5) by a factor of 30. Draw resonance structures to support your argument. (The p/Ca values refer to the corresponding ammonium ions.)... 

Anthracene has the formula Cl4Hln. It is similar to benzene but has 3 six-membered rings that share common C—C bonds, as shown below. Complete the structure by drawing in multiple bonds to satisfy the octet rule at each carbon atom. Resonance structures are possible. Draw as many as you can find. 

In 1999, Karl Christe synthesized and characterized a salt that contained the N,+ cation, in which the five N atoms are connected in a long chain. This cation is the first allnitrogen species to be isolated in more than 100 years. Draw the most important Lewis structure for this ion, including all equivalent resonance structures. Calculate the formal charges on all atoms. 

Draw resonance structures for the trimethylenemethane anion C(CH,) 2 in which a central carbon atom is attached to thi ee CH, groups (CH, groups are referred to as methylene). 

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