
To draw:
a) The Lewis structures for four resonance forms of linear N5-.
b) Calculate formal charges and identify the structures that contribute the most to the bonding in N5-.
c) By comparing Lewis structures for N5- and N3-, find out the ion in which the nitrogen-nitrogen bonds have the higher average bond order.

Answer to Problem 4.169QA
Solution:
a)
b) The last four structures having the lowest formal charge. These structures contribute the most to the bonding in N5-.
c)
From these resonance structures we see that each bond is predicted to be of double bond character in N3-. Therefore, in N5- there are two longer nitrogen-nitrogen bonds than in N3-. N3- has the higher average bond order.
Explanation of Solution
The ground state electronic configuration of N is 1s2 2s2 2p3.
Element | Valence electrons | ||
Symbol | # of atoms | In one atom | Total |
N | 5 | 5 | 25 |
One electron from -1 charge | 1 | ||
Valence electrons in molecule | 26 |
Each N atom is attached with single bond.
N - N - N - N - N
Eight electrons get involved in the bond formation. Now we put remaining electrons as lone pairs on the atoms.
The octet of terminal N atoms is get completed. The octet of remaining N is not get completed. For that we will convert some lone pairs into bond pairs.
Now we calculate the formal charge on each atom in second structure.
The Lewis structure with formal charge on N atom is as follows.
Now we draw the resonating structures of this molecule.
The molecules which having minimum formal charge will contribute the most to the bonding in N5-. Following structures having least formal charge and will contribute the most to the bonding in N5-.
Let’s we draw the Lewis structure of N3-.
Element | Valence electrons | ||
Symbol | # of atoms | In one atom | Total |
N | 3 | 5 | 15 |
One electron from -1 charge | 1 | ||
Valence electrons in molecule | 16 |
From these resonance structures we see that each bond is predicted to be of double bond character. Therefore, in N5- there are two longer nitrogen-nitrogen bonds than in N3-.
Bond order is the number of bonds between atoms. For single bond the bond order is 1. For double bond the bond order is 2. For triple bond the bond order is 3. From the resonance structure of N5- and N3-, we can say that N3- has the higher average bond order.
Conclusion:
From the electronic configuration of atoms in the molecule we can draw Lewis structure of the molecule. From the Lewis structure we can find out formal charge and bond order.
Want to see more full solutions like this?
Chapter 4 Solutions
CHEM:ATOM FOC 2E CL (TEXT)
- 11 Organic Chemistry Organic Nomenclature Practice Name/Functional Group n-butane Formula Structural Formula (1) C4tt10 H3C C- (2) CH3CH2CH2 CH 3 H₂ -CH3 Н2 name & functional group (1) and (2) OH H₁₂C Н2 name only (1) and (2) name only (1) and (2) H₁C - = - CH₂ Н2 HC=C-C CH3arrow_forwardUnder aqueous basic conditions, nitriles will react to form a neutral organic intermediate 1 that has an N atom in it first, and then they will continue to react to form the final product 2: NC H₂O он- H₂O 1 2 OH Draw the missing intermediate 1 and the final product 2 in the box below. You can draw the two structures in any arrangement you like. Click and drag to start drawing a structure.arrow_forwardAssign these COSY Spectrumarrow_forward
- Assign these C-NMR and H-NMR Spectrumarrow_forwardPredict the product of this organic reaction: IZ + HO i P+H₂O Specifically, in the drawing area below draw the skeletal ("line") structure of P. If there is no reasonable possibility for P, check the No answer box under the drawing area. No Answer Click and drag to start drawing a structure. ☐ :arrow_forwardPredict the products of this organic reaction: 0 O ----- A + KOH ? CH3-CH2-C-O-CH2-C-CH3 Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click anywhere to draw the first atom of your structure. X ⑤ èarrow_forward
- Predict the products of this organic reaction: O CH3 + H2O + HCI A A? CH3-CH2-C-N-CH3 Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. If there's more than one product, draw them in any arrangement you like, so long as they aren't touching. If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No Reaction Click anywhere to draw the first atom of your structure.arrow_forwardWhat is the missing reactant in this organic reaction? R+ HO-C-CH2-CH3 0= CH3 CH3 —CH, C−NH—CH CH3 + H₂O Specifically, in the drawing area below draw the condensed structure of R. If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check the No answer box under the drawing area. Note for advanced students: you may assume no products other than those shown above are formed. No Answer Click anywhere to draw the first atom of your structure. €arrow_forward个 CHEM&131 9267 - $25 - Intro to Mail - Hutchison, Allison (Student x Aktiv Learnin https://app.aktiv.com Draw the product of the reaction shown below. Ignore inorganic byproducts. + Na2Cr2O7 Acetone, H2SO4 Type here to search Dryng OH W Prarrow_forward
- Predict the products of this organic reaction: OH + NaOH A? Specifically, in the drawing area below draw the skeletal ("line") structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click and drag to start drawing a structure. ✓ Sarrow_forwardPredict the products of this organic reaction: CH3-C-O-CH2-CH2-C-CH3 + H₂O ? A Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click anywhere to draw the first atom of your structure. :☐ darrow_forwardDE d. Draw an arrow pushing mechanism for the following IN O CI N fo 人 P Polle DELL prt sc home end ins F5 F6 F7 F8 F9 F10 F11 F12arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





