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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Check out a sample textbook solutionChapter 5 Solutions
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
- Br NH₂ OH NH₂ CH3 A/RO/exception Circle the more acidic compound and determine the effect responsible for such observation using ARIO methods, or if its an exception to the rule. Please explain thanks.arrow_forwardCan you double check my work?arrow_forwardThe structure of ascorbic acid is shown below. Redraw the structure and circle the most acidic hydrogen. Briefly explain your selection.arrow_forward
- Explain why the C-H, bond is much more acidic than the C-H, bond in pentan-2-one. Select the single best answer. HH. perfar 0H, is more acidic than H, because loss of H, forms a resonance-stabilized conjugate base. H, is less acidic than H, because loss of H, forms a resonance-stabilized conjugate base. H, is more acidic than H, because loss of H, forms a resonance-stabilized conjugate base. a. H, is less acidic than H, because loss of H, forms a resonance-sta bilized conjugate base.arrow_forward3. Draw 1,3-cyclohexanedione and CIRCLE any a-acidic hydrogens (Box A). Place the number of a-acidic hydrogens in the small box (Box B). Are some a-acidic protons more acidic than others - place an asterisk (*) on any if present.arrow_forwardIdentify the most and the least acidic compound in each of the following sets. Leave the remaining answer in each set blank. a) 2,4-dinitrobenzoic acid: v p-nitrobenzoic acid: p-bromobenzoic acid: b) benzoic acid: v formic acid: v propanoic acid: c) cyclohexanol: v phenol: v benzoic acid:arrow_forward
- 1. Rank the following species in order of increasing acidity. Explain your reasons for ordering them as you do. HF NH3 H2SO4 CH3OH CH3COOH H3O+ H2O2. Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these compounds, and explain why the acidity increases so dramatically with substitution by nitro groups. CH4 CH3NO2 CH2(NO2)2 CH(NO2)3arrow_forwardPrackce Compare the two hydrogens shown in this compound and circle the one that is more acidic. H-N а. Draw the two possible conjugate bases in red b. For your answer above, circle which of the conjugate bases is more stable b. Briefly justify your answer in part b (more space on next page if you need it).arrow_forwardplease help?arrow_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