Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 2.SE, Problem 60AP
The azide
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The two compounds nitrogen dioxide and dinitrogen tetraoxide are introduced in Section 3.13.
(a) NO2 is an odd-electron compound. Draw the best Lewis diagrams possible for it, recognizing that one atom cannot achieve an octet configuration. Use formal charges to decide whether that should be the (central) nitrogen atom or one of the oxygen atoms.
(b) Draw resonance forms for N2O4 that obey the octet rule. The two N atoms are bonded in this molecule.
The two compounds nitrogen dioxide and dinitrogentetraoxide are introduced in Section 3.13.(a) NO2 is an odd-electron compound. Draw the bestLewis diagrams possible for it, recognizing that oneatom cannot achieve an octet configuration. Use formal charges to decide whether that should be the(central) nitrogen atom or one of the oxygen atoms.(b) Draw resonance forms for N2O4 that obey the octetrule. The two N atoms are bonded in this molecule.
Draw the two resonance structures of CINO, with N as the central atom. Give the formal
charges of all of the atoms.
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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- Although I3- is a known ion, F3- is not. (a) Draw the Lewis structure for I3- (it is linear, not a triangle). (b) One of your classmates says that F3 - does not exist because F is too electronegative to make bonds with another atom. Give an example that proves your classmate is wrong. (c) Another classmate says F3- does not exist because it would violate the octet rule.Is this classmate possibly correct? (d) Yet another classmatesays F3- does not exist because F is too small to make bonds tomore than one atom. Is this classmate possibly correct?arrow_forward(a) Determine the formal charge of oxygen in the following structure. If the atom is formally neutral, indicate a charge of zero. (b) Draw an alternative Lewis (resonance) structure for the compound given in part (a). Show the unshared pairs and nonzero formal charges in your structure. Don't use radicals. Formal charge on O 0arrow_forwardSome chemists believe that satisfaction of the octet rule should be the top criterion for choosing the dominant Lewis structure of a molecule or ion. Other chemists believe that achieving the best formal charges should be the top criterion. Consider the dihydrogen phosphate ion, HaPO, , in which the H atoms are bonded to O atoms. (a) What is the predicted dominant Lewis structure if satisfying the octet rule is the top eriterion? (b) What is the predicted dominant Lewis structure if achieving the best formal charges is the top criterion?arrow_forward
- Carbon, nitrogen, and oxygen form two different polyatomic ions: cyanate ion (NCO) and fulminate ion (CNO). Write Lewis structures for each anion, including near-equivalent resonance structures (do not add any arrows between structures) and indicating formal charges. The isocyanate ion also has two near-equivalent structures, but the formal charge on the nitrogen attom cannot be reduced to zero: Cyanate ion (NCO)arrow_forwardDraw Lewis structures for each of the following compounds. In each case, specify the number of valence electrons surrounding the central atom. (Assign lone pairs and radical electrons where appropriate.) (Assume the central atom does not contain an expanded octet.) (a) bromine dioxide (BrO2) (b) beryllium bromide (BeBr2) (c) phosphorus pentafluoride (PF5)arrow_forwardWrite a Lewis electron dot diagram for phosphoryl chloride,POCl3 (Fig. 3.29). Assign formal charges to all the atoms.arrow_forward
- For the next compounds/ions, draw two (2) appropriate Lewis structures. One structure must obey the octet rule and the other structure must be a non-octet obeying structure (octet deficient or octet expansion). Be sure to indicate which structure is the “best” structure and explain your choice formal charge arguments and any other points you deem important. (a) BeCl2 (b) POF3 (c) SO42−arrow_forwardA resonance hybrid is a structure that can be depicted by more than one valid Lewis structure. part1: Draw the major resonance form of fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized, and it should include all nonzero formal charges and all nonbonding electrons. part2: Draw the second most important resonance form of fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized, and it should include all nonzero formal charges and all nonbonding electrons. part3: Draw the least important resonance contributor for fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized and should include all nonzero formal charges and all nonbonding electrons.arrow_forward3) The molecule diphosphorus tetraoxide (P,O,) has two central atoms and four different resonance structures that do not violate the octet rule. Draw two of these resonance structures below. 4) The compound acetone is a common solvent. It has a chemical formula of CH,COCH, Acetone has three central atoms. (a) Draw the Lewis Dot structure for acetone. (b) Give the Ideal Bond Angle for all three central atoms. 5) Four covalent molecules are drawn below. :o: H. H-CH H H (1) (2) (3) (4) a) Define each of these molecules as polar or non-polar. (1) (2) (3) b) Describe the type of intermolecular force that each molecule would use: (1) (2) (3) (4)arrow_forward
- The carbonate anion, CO32- , is a resonance hybrid. Draw all of the important resonance structures for this molecule. If an atom has a nonzero formal charge, be sure the formal charge is shown clearly in the structure. Use the resonance structures to calculate the average formal charge on each O atom (which are all equivalent in the "true" structure). [Note: all of the important contributing resonance structures have octets around each atom that desires an octet.]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 a Lewis diagram for BrO4- in which the central Br atom has a formal charge of zero and show all NONZERO formal charges on all atoms. Note that the overall charge on this ion is -1.arrow_forward
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