Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 2, Problem 5LGP
Consider the molecular formula
If any of the 15 structures you drew have atoms where the formal charge is other than zero, indicate the formal charge on the appropriate atom(s) and the overall charge for the molecule.
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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.]
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Chapter 2 Solutions
Organic Chemistry
Ch. 2 - Practice Problem 2.1
Propose structures for two...Ch. 2 - Prob. 2PPCh. 2 - Prob. 3PPCh. 2 - Prob. 4PPCh. 2 - Prob. 5PPCh. 2 - Practice Problem 2.6
Using a three-dimensional...Ch. 2 - Practice Problem 2.7
Trichloromethane (, also...Ch. 2 - Prob. 8PPCh. 2 - Prob. 9PPCh. 2 - Practice Problem 2.10
Write bond-line structural...
Ch. 2 - Practice Problem 2.11 Although we shall discuss...Ch. 2 - Practice Problem 2.12 Write bond-line structural...Ch. 2 - Prob. 13PPCh. 2 - Practice Problem 2.14
One way of naming ethers is...Ch. 2 - Practice Problem 2.15 Eugenol is the main...Ch. 2 - Practice Problem 2.16
One way of naming amines is...Ch. 2 - Practice Problem 2.17 Which amines in Practice...Ch. 2 - Prob. 18PPCh. 2 - Prob. 19PPCh. 2 - Practice Problem 2.20
Write bond-line formulas for...Ch. 2 - Practice Problem 2.21
Write bond-line formulas for...Ch. 2 - Practice Problem 2.22
Write bond-line formulas for...Ch. 2 - Prob. 23PPCh. 2 - Practice Problem 2.24 Write another resonance...Ch. 2 - Prob. 25PPCh. 2 - Practice Problem 2.26
Which compound would you...Ch. 2 - Practice Problem 2.27 Arrange the following...Ch. 2 - Prob. 28PPCh. 2 - Prob. 29PCh. 2 - Identify all of the functional groups in each of...Ch. 2 - 2.31 There are four alkyl bromides with the...Ch. 2 - Prob. 32PCh. 2 - Classify the following alcohols as primary,...Ch. 2 - 2.34 Classify the following amines as primary,...Ch. 2 - Prob. 35PCh. 2 - Identify all of the functional groups in Crixivan,...Ch. 2 - 2.37 Identify all of the functional groups in...Ch. 2 - 2.38 (a) Indicate the hydrophobic and hydrophilic...Ch. 2 - Hydrogen fluoride has a dipole moment of 1.83 D;...Ch. 2 - 2.40 Why does one expect the cis isomer of an...Ch. 2 - Prob. 41PCh. 2 - Prob. 42PCh. 2 - Prob. 43PCh. 2 - 2.44 Consider each of the following molecules in...Ch. 2 - True or false: For a molecule to be polar, the...Ch. 2 - 2.46 Which compound in each of the following...Ch. 2 - Prob. 47PCh. 2 - The IR spectrum of propanoic acid (Fig. 2.16)...Ch. 2 - Prob. 49PCh. 2 - Write structural formulas for four compounds with...Ch. 2 - There are four amides with the formula C3H7NO. (a)...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - Prob. 54PCh. 2 - Prob. 55PCh. 2 - 2.56 Compound C is asymmetric, has molecular...Ch. 2 - 2.57 Examine the diagram showing an -helical...Ch. 2 - Prob. 1LGPCh. 2 - Prob. 2LGPCh. 2 - Prob. 3LGPCh. 2 - Consider the molecular formula C4H8O2. Predict...Ch. 2 - Consider the molecular formula C4H8O2. If any of...Ch. 2 - Prob. 6LGPCh. 2 - Consider the molecular formula.
7. Pick five...Ch. 2 - Prob. 8LGP
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- Write Lewis structures for these ions. Show all valence electrons and all formal charges. (a) Amide ion, NH2 (b) Bicarbonate ion, HCO3 (c) Carbonate ion, CO32 (d) Nitrate ion, NO3 (e) Formate ion, HCOO (f) Acetate ion, CH3COOarrow_forwardWrite the correct Lewis structure and assign a formal charge to each atom in fulminate ion, CNO.arrow_forwardFormamide, HC(O)NH2, is prepared at high pressures from carbon monoxide and ammonia, and serves as an industrial solvent (the parentheses around the O indicate that it is bonded only to the carbon atom and that the carbon atom is also bonded to the H and the N atoms). Two resonance forms (one with formal charges) can be written for formamide. Write both resonance structures, and predict the bond angles about the carbon and nitrogen atoms for each resonance form. Are they the same? Describe how the experimental determination of the HNH bond angle could be used to indicate which resonance form is more important.arrow_forward
- What is the formal charge on the indicated atom in each of the following species? (a) sulfur in SO2 (b) nitrogen in N2H4 (c) each oxygen atom in ozone, O3arrow_forwardA complete Lewis structure must show all nonzero formal charges. Complete each of thefollowing Lewis structures by adding any missing formal charges.arrow_forwardPlease don't provide handwritten solution.arrow_forward
- For the phosphoric acid molecule (H3PO4), all four oxygen atoms are bonded to the central phosphorus atom and the three hydrogen atoms are bonded to different oxygen atoms. Several resonance structures can be drawn for H3PO4 but one structure is more important than the others. In the most important structure, the phosphorus atom has: a formal charge of +1 and a complete octet a formal charge of zero and a complete octet a formal charge of −1 and an expanded octet a formal charge of +5 and an expanded octet a formal charge of zero and an expanded octetarrow_forwardCalculating Formal Charge: Formal charge is calculated for each atom in a structure. It provides information about the stability and reactivity of the atom in the molecule. Formal Charge = Valence Electrons - 1/2 Bonding Electrons - Non-bonding Electrons For example, the formal charge on the carbon of methane is calculated here. Carbon has 4 valence electrons. There are 8 bonding electrons around it. Formal Charge4- 12 (8) -0 Calculate the formal charge on the circled atoms in the following structures. formal charge: Incorect formal charge: formal charge: 1 Incomectarrow_forwardI had gotten this one incorrect, but i wanted to use it to study, so please give me the solution to all parts of this question.arrow_forward
- The most likely Lewis dot structures are those that have small formal charges or no formal charges, especially for the central atom. They also have negative formal charges associated with the atoms of higher electronegativity and positive formal charges assigned to the atoms of lower electronegativity. O True O Falsearrow_forward+ Write a Lewis structure for the ammonium ion, NH4™. Explicitly draw all H atoms. Include all valence lone pairs in your answer. Include all nonzero formal charges. Do not use the square brackets tool in your answer. P aste opy [*arrow_forwardFormal charges and bonds are shown correctly in this Lewis structure, but lone pairs might be drawn wrong. Add or remove lone pairs to fix the structure. If no corrections need to be made, please check the box below. H O H ·O· C с H 1 H \ N H C 1 C-N H + H H H B X c+ 5 C Q:arrow_forward
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