Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 2.SE, Problem 62AP
Thiamin diphosphate (TPP), a derivative of vitamin B1 required for glucose
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Write a Lewis structure for the amide ion, NH2─, and assign formal charges to each atom.
Carbon, nitrogen, and oxygen form two different polyatomic ions: cyanate ion (NCO) and fulminate ion (CNO). Write Lewis
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Cyanate ion (NCO)
Which of the following bonds are polar: (a) P—O; (b) S—F; (c) Br—Br; (d) O—Cl? Which is the more electronegative atom in each polar bond?
Chapter 2 Solutions
Organic Chemistry
Ch. 2.1 - Prob. 1PCh. 2.1 - Prob. 2PCh. 2.1 - Use the electronegativity values shown in Figure...Ch. 2.1 - Look at the following electrostatic potential map...Ch. 2.2 - Ethylene glycol, HOCH2CH2OH, may look nonpolar...Ch. 2.2 - Make three-dimensional drawings of the following...Ch. 2.3 - Calculate formal charges for the nonhydrogen atoms...Ch. 2.3 - Organic phosphate groups occur commonly in...Ch. 2.6 - Which of the following pairs of structures...Ch. 2.6 - Draw the indicated number of resonance forms for...
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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- Write the correct Lewis structure and assign a formal charge to each atom in fulminate ion, CNO.arrow_forwardWrite the skeletal four Lewis structures of nitrosyl chloride, NOCI, one of the oxidizing agents present in aqua regia. Determine the best Lewis structure. Explain your answer with assigning formal charges for each structure.arrow_forwardWhat is the formal charge of the central atom of chlorite ion? O-2 O-1 O +2 O +1arrow_forward
- With reference to the “Chemistry Put to Work” box on explosives, (a) use bond enthalpies to estimate the enthalpy change for the explosion of 1.00 g of nitroglycerin. (b) Write a balanced equation for the decomposition of TNT. Assume that, upon explosion, TNT decomposes into N2(g), CO2(g), H2O(g), and C(s).arrow_forwardWhich of the following statements concerning the structures below is/are true? Formal charges are not shown. You can select more than one, or none, of these statements. (i) (ii) (iii) Ö (iv) The total charge on this species is zero. The formal charge of Cl is -3 in structure (i). CI has an expanded octet in all of these structures. The formal charge of Cl is +1 in structure (iii). Structures (ii), (iii), and (iv) are all unrealistic because, in each, there are too many electrons around O Cl. On the basis of formal charges, structure (i) is the most important structure.arrow_forwardDraw the two resonance structures of CINO, with N as the central atom. Give the formal charges of all of the atoms.arrow_forward
- Which of the Lewis structures for NO is dominantly based on analysis of the formal charges?arrow_forwardSulfuric acid is the industrial chemical produced in greatest quantity worldwide. About 90 billion pounds are produced each year in the United States alone. Write the Lewis structure for sulfuric acid, H2SO4, which has twooxygen atoms and two OH groups bonded to the sulfur.arrow_forwardAssign formal charges to each atom in the interhalogen ion ICl4−.arrow_forward
- 19. :O: || :0-N- O: Which of the following statements, if true, would support the claim that the NO3 ion, represented above, has three resonance structures? (A) The NO3 ion is not a polar species. (B) The oxygen-to-nitrogen-to-oxygen bond angles are 90°. (C) One of the bonds in NO3 is longer than the other two. (D) One of the bonds in NO3¯ is shorter than the other two.arrow_forwardThe azide ion, N3 -, is a symmetrical ion, and all of its contributing resonance structures have formal charges. Draw three important contributing structures for this ion.arrow_forward(b) The Murchison meteorite that landed in Australia in 1969 contained 92 different amino acids, including 21 found in Earth organism A skeleton structure (single bond only) of one of these extraterrestrial amino acids is shown below. Draw a Lewis structure, and identify any atoms having a nonzero formal charge. H3N. C ČH2 ČH3 (c) Draw the orbital diagrams and Lewis symbols to depict the formation of Na* and CI ions from the atoms. Give the formula of the compound formed. (d) The predicted bond length for HF is 109 pm (the sum of the covalent radii of H, 37 pm and F, 72 pm), however the actual bond length for HF is shorter (92 pm). It was observed that the difference between predicted and actual bond lengths becomes smaller going down the halogen group from HF to HI Describe these observationsarrow_forward
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