Organic Chemistry
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Predict the structure of the anion formed by the abstraction of a proton from the following compound using NaOH. Also, draw the important resonance forms involved in the stabilization of this anion.
Provide the resonance structure that would form according to the electron flow indicated by the arrow-pushing formalism on the structure given below:
Some pairs of structures are given at the end of the question. Recognize each of these pairs as different entities or resonance forms of the same compound.
Draw the significant resonance structures for each of the two resonance-stabilized cations shown below.
Resonance structures show the delocalization of electrons in a structure. Draw all possible resonance structures for the following free radical:
Determine all the pushable electron pairs and the places where the electrons can be pushed for the structure below. Also, provide one valid resonance structure.
Two valid resonance structures of a molecule are shown below. Illustrate the electron flow in the structure on the left by adding an arrow-pushing formalism to form the structure on the right.
Draw the resonance structures of the following compounds and mark the regions of high and low electron densities.
Draw the resonance structure(s) that will help explain why (a) nucleophiles, (b) electrophiles, and (c) H + add according to the regioselectivity shown.
Show all the possible resonance structures of SO3.
Consider the following molecule:
Provide the resulting resonance structure according to the electron flow indicated by the arrow-pushing formalism.
Illustrate all valid resonance structures for the following:
Draw resonance forms of the peptide linkage in the dipeptide given below.
Compare the resonance forms of trisulfur (S3) and ozone (O3). There is an additional structure possible for trisulfur which was not present with ozone. Explain the reason behind this additional resonance form for trisulfur.
5-Chloro-1,3-cyclohexadiene (a secondary alkyl halide) can give SN1 substitution reactions at a rate comparable to that of a tertiary alkyl halide. Draw the resonance stabilized intermediates to explain the increased reactivity of the compound.
The structure of nitrate ion is given below.
a. Predict the relative bond length of each bond.
b. What is the charge on each oxygen atom?
The given structure contains three nitrogen atoms having different basic strengths. Draw the significant resonance structures of the products formed by the protonation of each of these nitrogen atoms.
The following pair of structures depict two valid resonance structures. Illustrate the formation of the structure on the left by adding an arrow-pushing formalism on the structure on the right.
The following figure illustrates two valid resonance structures of a molecule. With an arrow-pushing mechanism, show the electron flow in the left structure to form the structure on the right.
Draw the resonance structures of the below-given species. Also, draw the resonance hybrid and indicate their relative contribution to the resonance hybrid.
Draw the resonance structures of the enolate ions produced by the deprotonation of the below-given compounds through a base.a. cyclopentane-1,3-dioneb. methyl acetoacetate
Draw the resonance structures for the given ion while disregarding highly unstable structures with minimal contribution to the resonance hybrid. Identify the major and minor contributors. Consider that the ion may have resonance structures that exhibit equal contributions to the resonance hybrid.
Draw the resonance forms for the following ions and mark the major contributors.
Sketch the other resonance structure that involves the oxygen's lone pair in the structure given. Determine the nucleophilic carbon/s.
Consider the following:
Provide all the resonance structures of the given carbocation and carbanion.
Draw the resonance forms of the allylic carbocations produced as a result of ionization of the following allylic halides.
Consider the following pair of structures:
These depict two valid resonance structures. Show the formation of the structure on the left by adding an arrow-pushing formalism on the structure on the right.
Show the significant resonance structures for each of the given compounds.
a.
b.
c.
Illustrate the resonance structures for the radical below.
For these two sets of resonance forms, determine the major and minor resonance structures. Also, identify structures of equal energy and add any missing important resonance structures.
Give the resonance structures for the ions mentioned below.
Provide the structures of significant resonance contributors for the given free radical.
Draw all the resonance contributors of the given compound and predict their relative stabilities. Also, draw its resonance hybrid.
Based on the structure below, determine the number of pushable electron pairs in the molecule:
Predict the species with delocalized electrons from the list below.
Sketch the other resonance structures that involve the C―O and C―C π bonds in the structure given. Determine the carbon/s where a nucleophile would attack.
Do these ions have other resonance forms? Draw the structures of possible resonance forms in each case.a. ClO3-b. HSO4-c.
Determine how many atoms share the free radical electron in the given species.
Phenoxy radical
From a list of resonance structures shown below, select all structures that contribute to the delocalization of the negative charge in a derivative of the Ruhemann's purple anion.
The following figure depicts two resonance structures of a molecule. Add two arrow-pushing formalisms to the structure on the left to illustrate its electron flow to form the structure on the right.
Draw the significant resonance forms of the below-given species. Also, draw the resonance hybrid and indicate their relative contribution to the resonance hybrid.
Draw all the significant resonance forms for the ion given below.
Determine whether each of the following pairs of structures represents two different compounds or resonance contributors of the same compound.
Draw all of the significant resonance structures of the given ion.
The figure below represents two resonance structures of a molecule. Show the electron flow in the structure on the left by adding an arrow-pushing formalism to form the structure on the right.
Determine which ion is more stable for each pair. Use resonance forms to explain your answers.
Draw the resonance forms of the compound given below. Also, draw the resonance contributors and indicate their relative contribution to the resonance hybrid.
Isobutyronitrile is a weakly acidic compound and can only be deprotonated using a very strong base. Draw the resonance structures to show the stability of the resulting carbanion.
Show the resonance structure that will be formed from the electron flow indicated by the arrow-pushing formalism in the following structure:
An ester has two oxygen atoms, each with two nonbonding pairs of electrons. Draw and compare the resonance forms of the cations produced when protonation occurs at:
a) Alkoxy oxygen
b) Carbonyl oxygen
Suggest which of the two oxygen atoms is more basic, and give a suitable reason for your answer.
Draw all the resonance contributors of the given species and predict their relative stabilities. Also, draw its resonance hybrid.
Write the appropriate resonance structures for these two radicals CH3CH2COO・ and
Draw all the significant resonance structures of phenylmethylium ion
Benzyl chloride undergoes SN1 substitution at a rate almost equal to that of a tertiary halide although it is a primary halide. Draw its resonance forms to explain this increased reactivity.
Predict whether each species in the following list will have delocalized electrons or not.
Provide the resonance structures of the following radical:
Is the carbon-nitrogen single bond in a primary amide longer or shorter than that in a primary amine? Explain.
Show the resonance forms for the ion given below.
Provide the resonance forms of the radical shown below.
Show the resonance structures for the radical species given below.
Determine which among the listed species below possess delocalized electrons.