Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 2, Problem 17E
(a)
Interpretation Introduction
Interpretation: A molecule containing a carbon with a -1 formal charge should be drawn.
Concept introduction: Having an extra electron around an atom gives a -1 formal charge to that atom.
(b)
Interpretation Introduction
Interpretation: A molecule containing a carbon with a +1 formal charge should be drawn.
Concept introduction: Losing 1 electron around an atom from its ground state gives a +1 formal charge to that atom.
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Consider the generic polyatomic ion XY3". Element X is the least electronegative. For neutral
atoms, element X has 7 valence electrons and element Y has 6. The highest occupied principal
energy level of the central atom is greater than 2.
A. How many total valence electrons are in the molecule.
B. Draw a BEST Lewis structure (i.e. a major resonance contributor) for this molecule. Show all
valence electrons on your structure.
C. If you haven't already, add the formal charge of each atom to the structure. Show at least one
sample calculation for formal charge.
D. Outline 4 short bullet points (~several words each) that explain why your structure from part B is
the best one. Hint: think about what makes a valid structure and what makes a best structure.
E. Perform a calculation to determine the average bond order between the X and Y atoms in your
structure from part B. No credit will be given for just a number.
F. Draw one more valid resonance structure other than the one from part B.…
8. Compute for the formal charge (FC) on each atom in the following compounds.
a. H3N - BH3
b. [H2CNH2]+
c. H3O+
d. HCO3-
9. Draw Lewis structures for the following compounds, showing an appropriate formal charges.
a. [CH3OH2]+
b. [HONH3]+
c. NaBH3CN
d. CH3NH3+
10. For each of the following compounds, draw the important resonance forms. Indicate which structures are major and minor contributors or whether they would have the same energy.
a. [CH3OCH2]+
b. H2SO4
c. CO3-2
d. H2C=CH-+CH2
e. [CH3C(OCH3)2 ]+
11. Draw the complete Lewis structures for the following condensed structural formulas.
a. CH3(CH2)3CH(CH3)2
b. CH3CH2COCN
c. (CH3)3CCOCHCH2
d. (CH3CH2)2CO
e. (CH3)2CHCH2Cl
12. Draw the line-angle formula for the following condensed structural formulas.
a. CH3(CH2)3CH(CH3)2
b. CH3CH2COCN
c. (CH3)3CCOCHCH2
d. (CH3CH2)2CO
e. (CH3)2CHCH2Cl
8. Compute for the formal charge (FC) on each atom in the following compounds.
a. H3N - BH3
b. [H2CNH2]+
c. H3O+
d. HCO3-
9. Draw Lewis structures for the following compounds, showing an appropriate formal charges.
a. [CH3OH2]+
b. [HONH3]+
c. NaBH3CN
d. CH3NH3+
10. For each of the following compounds, draw the important resonance forms. Indicate which structures are major and minor contributors or whether they would have the same energy.
a. [CH3OCH2]+
b. H2SO4
c. CO3-2
d. H2C=CH-+CH2
e. [CH3C(OCH3)2 ]+
11. Draw the complete Lewis structures for the following condensed structural formulas.
a. CH3(CH2)3CH(CH3)2
Chapter 2 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 2 - Prob. 1CTQCh. 2 - The valence shell of an atom in a legitimate Lewis...Ch. 2 - Prob. 3CTQCh. 2 - Prob. 4CTQCh. 2 - Prob. 5CTQCh. 2 - It is impossible to draw a legitimate Lewis...Ch. 2 - Describe how to calculate the total number of...Ch. 2 - Prob. 8CTQCh. 2 - Prob. 9CTQCh. 2 - Prob. 10CTQ
Ch. 2 - Prob. 11CTQCh. 2 - Prob. 12CTQCh. 2 - A complete Lewis structure must show all nonzero...Ch. 2 - Prob. 14CTQCh. 2 - Prob. 15CTQCh. 2 - Prob. 16CTQCh. 2 - Prob. 17CTQCh. 2 - Prob. 18CTQCh. 2 - Complete the rest of the table for N, O or X by...Ch. 2 - Prob. 20CTQCh. 2 - Prob. 21CTQCh. 2 - Make a checklist that can be used to determine if...Ch. 2 - Prob. 2ECh. 2 - Prob. 3ECh. 2 - Draw the Lewis structure of a neutral molecule...Ch. 2 - Prob. 5ECh. 2 - For each element, predict (and draw a Lewis...Ch. 2 - Predict which of the following species is least...Ch. 2 - The molecules BH3 and SF6 and the ion SO42 exist...Ch. 2 - These are NOTlegitimate Lewisstructures (and...Ch. 2 - Fill in missing formal charges where needed (all...Ch. 2 - Below each structure in the previous question is a...Ch. 2 - Prob. 12ECh. 2 - Carbon monoxide (CO) is an example of an overall...Ch. 2 - Explain why this Lewis structure for CO is not as...Ch. 2 - Prob. 15ECh. 2 - Prob. 16ECh. 2 - Prob. 17ECh. 2 - Prob. 18ECh. 2 - Prob. 19E
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- On the left side of Figure 3.6, label the areas shown with a dotted line where... one bond can form. one bond can form.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_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.arrow_forward
- a.)Draw a Lewis diagram for IO4- in which the central I atom has a formal charge of zero and show all NONZERO formal charges on all atoms. note overall charge of ion is -1 b.)Draw a Lewis structure for IO4- in which the octet rule is satisfied on all atoms and show all NONZERO formal charges on all atoms. C.Based on formal charge, what is the best Lewis structure for the ion? smallest formal charge or octet rule satisfied for all atomsarrow_forwardAn incomplete Lewis structure is shown below. The structure only shows the atoms and how they are connected. The molecule has a net charge of zero. H H. H. Complete the Lewis structure giving all atoms full octets. It there is more than one way to do this, draw resonance structures showing all posibilities. If not just draw one Lewis structure. Be sure to wite in any non-zero formal charges. Click and drag to start drawing a structure. 2.arrow_forwardNhy is resonance structure A and resonance structure B not the same structure? If you rotate the molecule like a spicket handle (l. e. clockwise with the C at the center and the R group remaining in place as you look down the C - R bond) wouldn't you get the same thing? Why are these not equivalent structures? Resonance structure A t Resonance structure B Actual structurearrow_forward
- 2. Provide the best Lewis structure for each molecule below. Include all lone pairs and formal charges but C-H can be omitted. D. Trifluoromethylsulfonic acid (F3CSO2OH)arrow_forwardll X b My Questions | bartleby Login | bartleby 101 Chem101 ぐ app.101edu.co Question 1 Draw a resonance structure that shifts a pi bond to a new position. Don't increase the number of atoms with formal charges. Include all hydrogen atoms in your structure. H. Atoms, Bonds an Drawing CHa :CHs: %3. 3D CH2 CH2 MacBook 0:0 3D 3Darrow_forwardA student once drew the following arrows and resonance structure for me (their work is in blue). List two things that make what the student drew incorrect. Then, tell me how you knew that the two things you listed were incorrect answers. Yes, there are more than two things incorrect here, but only tell me about two of them. :0: :O: H động đang H H H Edit View Insert Format Tools Table 12pt Paragraph BI U A 2v T²v |arrow_forward
- O REPRESENTATIONS OF ORGANIC MOLECULES Completing the Lewis structure for an organic molecule with no.. The incomplete Lewis structure below shows all the atoms and sigma bonds for a particular molecule, but nothing else. The molecule has a net charge of +1. Fill in any missing electrons to create the best Lewis structure for the molecule. Make sure to include any non-zero formal charges. H H H. H. H. toarrow_forwardFormal Charge When more than one resonance structure is possible, the determination of the best structure can made based on the formal charges in the structure. The calculation of the formal charge is given by: Formal Charge = # valence electrons - % bonding electrons - lone pair electrons We determined that the structure of BFs is an exception to the octet rule (see above). 4. a) Determine the formal charge on B and F in this structure. Valence e on B Valence e on F -½ bonding e- lone pair e= -½ bonding e- lone pair e= We could draw a different resonance structure by moving a lone pair of electrons off one of the F atoms and make a second bond to the B atom (see figure on next page): Student Name: Date: b) The octet rule is obeyed, but this is not the structure of BF3. To see why it is not, determine the formal charges of B and F in this second structure. Valence e on B 3-% 8 bonding e- 0 lone pair e= Valence e on F1-% 1 bonding e- 2 lone pair e = +1 The formal charges are non-zero…arrow_forward2. Indicate the formal charge on each carbon atom in the examples below. All lone pairs are shown. H H HC- -H H—C—H H C H H H- H C -H H 3. Keeping in mind that all row two elements need to have 8 electrons and each bond contains two electrons, draw the missing lone pair electrons on each O or N below. Then, assign the missing formal charges to each O or N. +*+*arrow_forward
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