Concept explainers
Interpretation:The most acidic hydrogen in pair of molecules given below should be circled. Also, molecule that haslower value of
Concept introduction:Lewis structure is representation of molecule in which dots are shown to represent unshared electrons and lines are shown to represent bonds. These lines and dots represent distribution of the electrons in the molecule.
When one single structure is unable to describe all the properties of single molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.
Rules to form resonance structure are as follows:
1. Use arrow types 1 and 2 for resonance structure of anions in movement of negative charge.
2. Use only arrow type 3 to move a positive charge for resonance structure of cations.
3. The sigma bond should not be broken. Any atom must not move from its place and total number of electrons must be same in all resonance structures.
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Organic Chemistry: A Guided Inquiry
- For each molecule below, draw the conjugate acid or conjugate base or both if the molecule hasboth a conjugate acid and a conjugate base (e.g., water).arrow_forwardComplete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)arrow_forwardComplete each Lewis structure, draw all important resonance structures, predict a value for thebond angles requested, and explain your reasoning. a. Nitrous acid (HNO2)HONOHON=ONO= b. Enolate ion (C2H3O) HC1C2=HC2C1=arrow_forward
- Draw the most stable conjugate acid of this molecule. BrieUly explain your choice in thespace providedarrow_forwardConsider the below molecule and its hydrogen atoms labeled a through e. Rank the named hydrogen atoms in order of increasing acidity. Explain your choice.arrow_forward1. Explain why the protonation of pyrrole occurs at C2 to form A, rather than the N atom to form B 2. Explain why compound A is more acidic than C, the conjugate acid of pyridine. :N-H H H H -H Pyrrole pKa=0.4 pKa=5.3 A B C Harrow_forward
- For each pair of compounds, circle the one that is more acidic. Briefly explain why your choice is the more acidic one. Your answer should involve qualitative principles (not just the pKa's given), and you should include structural drawings.arrow_forwardPlace the following compounds in order of their basicity with #1 being the most basic and #4 being the least basic. Work carefully. There will be no partial credit or regrades on this problem. 'N' CH3 N. Z-Iarrow_forwardRank the compounds or ions in order of increasing acidity (or decreasing p?a).arrow_forward
- Draw the major organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions. H I N. NaOH H oarrow_forwardDecide which compound and each pair is more acidic. (Please explain)arrow_forwardFrom each pair, select the stronger base. Then draw the conjugate acid of the strong base below. CH3CH20 or CH3CEC • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • You do not have to include lone pairs in your answer. C opy astearrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning