Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 2.SE, Problem 60AP
The azide functional group, which occurs in azidobenzene, contains three adjacent nitrogen atoms. One resonance structure for azidobenzene is shown. Draw three additional resonance structures, and assign appropriate formal charges to the atoms in all four.
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The azide ion, N3 - , is a symmetrical ion, all of whose contributing resonance structures have formal charges. Draw three important contributing structures for this ion.
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Chapter 2 Solutions
Organic Chemistry
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Ch. 2.7 - Nitric acid (HNO3) reacts with ammonia (NH3) to...Ch. 2.8 - Prob. 12PCh. 2.8 - Amide ion, H2N-, is a much stronger base than...Ch. 2.9 - Prob. 14PCh. 2.9 - Prob. 15PCh. 2.9 - Prob. 16PCh. 2.11 - Using curved arrows, show how the species in part...Ch. 2.11 - Prob. 18PCh. 2.12 - Of the two vitamins A and C, one is hydrophilic...Ch. 2.SE - Prob. 20VCCh. 2.SE - The following model is a representation of...Ch. 2.SE - cis-l, 2-Dichloroethylene and trans-1,...Ch. 2.SE - The following molecular models are representations...Ch. 2.SE - Predict the product(s) of the acid/base reactions...Ch. 2.SE - Use curved arrows to draw the protonated form of...Ch. 2.SE - Prob. 26MPCh. 2.SE - Double bonds can also act like Lewis bases,...Ch. 2.SE - Prob. 28APCh. 2.SE - Use the electronegativity table given in Figure...Ch. 2.SE - Which of the following molecules has a dipole...Ch. 2.SE - Prob. 31APCh. 2.SE - Phosgene, C12C=O, has a smaller dipole moment than...Ch. 2.SE - Prob. 33APCh. 2.SE - Methanethiol, CH3SH, has a substantial dipole...Ch. 2.SE - Calculate the formal charges on the atoms shown in...Ch. 2.SE - Assign formal charges to the atoms in each of the...Ch. 2.SE - Which of the following pairs of structures...Ch. 2.SE - Prob. 38APCh. 2.SE - 1, 3-Cyclobutadiene is a rectangular molecule with...Ch. 2.SE - Alcohols can act either as weak acids or as weak...Ch. 2.SE - The O-H hydrogen in acetic acid is more acidic...Ch. 2.SE - Draw electron-dot structures for the following...Ch. 2.SE - Write the products of the following acid-base...Ch. 2.SE - Rank the following substances in order of...Ch. 2.SE - Which, if any, of the substances in Problem 2-44...Ch. 2.SE - The ammonium ion (NH4+, pKa = 9.25) has a lower...Ch. 2.SE - Prob. 47APCh. 2.SE - Prob. 48APCh. 2.SE - Calculate Ka values from the following pka’s:...Ch. 2.SE - Calculate pKa values from the following Ka’s:...Ch. 2.SE - What is the pH of a 0.050 M solution of formic...Ch. 2.SE - Prob. 52APCh. 2.SE - Maleic acid has a dipole moment, but the closely...Ch. 2.SE - Assume that you have two unlabeled bottles, one of...Ch. 2.SE - Identify the acids and bases in the following...Ch. 2.SE - Which of the following pairs represent resonance...Ch. 2.SE - Draw as many resonance structures as you can for...Ch. 2.SE - Carbocations, which contain a trivalent,...Ch. 2.SE - We’ll see in the next chapter that organic...Ch. 2.SE - The azide functional group, which occurs in...Ch. 2.SE - Phenol, C6H5OH, is a stronger acid than methanol,...Ch. 2.SE - Thiamin diphosphate (TPP), a derivative of vitamin...Ch. 2.SE - Determine if each compound or ion below has a...Ch. 2.SE - Prob. 64APCh. 2.SE - Prob. 65APCh. 2.SE - Draw the conjugate base for each compound below...Ch. 2.SE - 1, 1, 1-Trichloroethanol is an acid more than 1000...
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- Two Lewis structures can be written for nitrosyl fluoride, which contains one nitrogen, one oxygen, and one fluorine atom per molecule. Write the two Lewis structures land assign a formal charge to each atom.arrow_forwardDraw resonance structures for each of these ions: NSO− and SNO−. (The atoms are bonded in the order given in each case, that is, S is the central atom in NSO−.) Use formal charges to determine which ion is likely to be more stable. Explain why the two ions cannot be considered resonance structures of each other.arrow_forwardThree known isomers exist of N2CO, with the atoms in these sequences: NOCN; ONNC; and ONCN. Write resonance structures for each isomer and use formal charge to predict which isomer is the most stable.arrow_forward
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- The hypochlorite ion, ClO-, is the active ingredient inbleach. The perchlorate ion, ClO4-, is a main componentof rocket propellants. Draw Lewis structures for both ions. (a) What is the formal charge of Cl in the hypochlorite ion?(b) What is the formal charge of Cl in the perchlorate ion, assumingthe Cl—O bonds are all single bonds? (c) What is theoxidation number of Cl in the hypochlorite ion? (d) Whatis the oxidation number of Cl in the perchlorate ion, assumingthe Cl—O bonds are all single bonds? (e) In a redox reaction,which ion would you expect to be more easily reduced?arrow_forwardUse formal charge to explain why the fulminate ion is less stable (and therefore less reactive) than the cyanate ionarrow_forwardWrite a Lewis structure for the amide ion, NH2─, and assign formal charges to each atom.arrow_forward
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