Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 1, Problem 43P
Consider a chemical species (either a molecule or an ion) in which a carbon atom forms three single bonds to three hydrogen at-oms and in which the carbon atom possesses no other valence electrons. (a) What formal charge would the carbon atom have? (b) What total charge would the species have? (c) What shape would you expect this species to have? (d) What would you expect the hybridization state of the carbon atom to be?
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The structure at the right is a skeleton of an anion having the overall formula C6H,NO¯. The hydrogen
atoms are not shown.
(a) Draw a complete Lewis structure in which the -1 formal charge is on N. Include all H atoms and
C.
valence electrons.
(b) Do the same for a Lewis structure with the -1 formal charge on O.
(c) Do the same for a Lewis structure with the -1 formal charge on the C atom that is bonded to three other C atoms.
Draw the shapes of the following molecules and ions in 3-dimension. Show clearly any lone pairs of electrons on the central atom, state the number of bond pairs and lone pairs of electrons on the central atom and name the shape of the molecule or ion.
(a) AIH4-, aluminium hydride ion
(b) CH3-, methyl carbanion
(c) POCl3, phosphorus oxychloride
Provide everything stated in the instructions for each compound.
The partial Lewis structure that follows is for a hydrocarbonmolecule. In the full Lewis structure, each carbon atomsatisfies the octet rule, and there are no unshared electronpairs in the molecule. The carbon—carbon bondsare labeled 1, 2, and 3. (a) How many hydrogen atomsare in the molecule? (b) Rank the carbon–carbonbonds in order of increasing bond length. (c) Whichcarbon—carbon bond is the strongest one? [Sections 8.3and 8.8]
Chapter 1 Solutions
Organic Chemistry
Ch. 1 - Prob. 1PPCh. 1 - Prob. 2PPCh. 1 - Prob. 3PPCh. 1 - Prob. 4PPCh. 1 - Prob. 5PPCh. 1 - Prob. 6PPCh. 1 - Prob. 7PPCh. 1 - Prob. 8PPCh. 1 - Prob. 9PPCh. 1 - Prob. 10PP
Ch. 1 - Prob. 11PPCh. 1 - Prob. 12PPCh. 1 - Prob. 13PPCh. 1 - Prob. 14PPCh. 1 - Prob. 15PPCh. 1 - Prob. 16PPCh. 1 - Prob. 17PPCh. 1 - Prob. 18PPCh. 1 - Prob. 19PPCh. 1 - Prob. 20PPCh. 1 - Prob. 21PPCh. 1 - Practice Problem 1.22 Which of the following...Ch. 1 - Prob. 23PPCh. 1 - Prob. 24PPCh. 1 - Practice Problem 1.25
What do the bond angles of...Ch. 1 - Prob. 26PPCh. 1 - Practice Problem 1.27
Use VSEPR theory to predict...Ch. 1 - Practice Problem 1.28 Predict the bond angles of...Ch. 1 - 1.29 Which of the following ions possess the...Ch. 1 - 1.30 Write a Lewis structure for each of the...Ch. 1 - Prob. 31PCh. 1 - Add any unshared electrons to give each element an...Ch. 1 - Prob. 33PCh. 1 - What is the molecular formula for each of the...Ch. 1 - Prob. 35PCh. 1 - Prob. 36PCh. 1 - 1.37 Write bond-line formulas for all of the...Ch. 1 - Prob. 38PCh. 1 - Prob. 39PCh. 1 - Prob. 40PCh. 1 - Prob. 41PCh. 1 - (a) Cyanic acid (HOCN) and isocyanic acid (HN=C=O)...Ch. 1 - Consider a chemical species (either a molecule or...Ch. 1 - 1.44 Consider a chemical species like the one in...Ch. 1 - 1.45 Consider another chemical species like the...Ch. 1 - Draw a three-dimensional orbital representation...Ch. 1 - Ozone (O3) is found in the upper atmosphere where...Ch. 1 - Write resonance structures for the azide ion, N3....Ch. 1 - Write structural formulas of the type indicated:...Ch. 1 - Prob. 50PCh. 1 - 1.51 In Chapter 15 we shall learn how the...Ch. 1 - Prob. 52PCh. 1 - (a) Consider a carbon atom in its ground state....Ch. 1 - Open computer molecular models for dimethyl ether,...Ch. 1 - Boron is a group IIIA element. Open the molecular...Ch. 1 - 1.56 There are two contributing resonance...Ch. 1 - Prob. 1LGPCh. 1 - Consider the compound with the following condensed...Ch. 1 - Consider the compound with the following condensed...Ch. 1 - Consider the compound with the following condensed...Ch. 1 - Consider the compound with the following condensed...Ch. 1 - Consider the compound with the following condensed...Ch. 1 - Prob. 7LGPCh. 1 - Prob. 8LGP
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The partial Lewis structure that follows is for a hydrocarbonmolecule. In the full Lewis structure, each carbon atomsatisfies the octet rule, and there are no unshared electronpairs in the molecule. The carbon—carbon bondsare labeled 1, 2, and 3. (a) How many hydrogen atomsare in the molecule? (b) Rank the carbon–carbonbonds in order of increasing bond length. (c) Whichcarbon—carbon bond is the strongest one?arrow_forwardThe compound SF3N has been synthesized. (a) Draw the Lewis diagram of this molecule, supposing that the three fluoride atoms and the nitrogen atom surround the sulfur atom. Indicate the formal charges. Repeat, but assume that the three fluorine atoms and the sulfur atom surround the nitrogen atom. (b) From the results in part (a), speculate about which arrangement is more likely to correspond to the actual molecular structurarrow_forwardThere is persuasive evidence for the brief existence of the unstable molecule OPCl. (a) Draw a Lewis diagram for this molecule in which the octet rule is satisfied on all atoms and the formal charges on all atoms are zero. (b) The compound OPCl reacts with oxygen to give O2PCl. Draw a Lewis diagram of O2PCl for which all formal charges are equal to zero. Draw a Lewis diagram in which the octet rule is satisfied on all atoms.arrow_forward
- The connectivity of carbon oxysulfide is OCS. (a) Write a Lewis formula for carbon oxysulfide that satisfies the octet rule. (b) What is the molecular geometry according to VSEPR? (c) Does carbon oxysulfide have a dipole moment? If so, what is its direction?arrow_forward(a) Add the lone pairs to this structure and draw a valid resonance structure for it that has octets on all of the heavy atoms (i.e., non-hydrogen atoms). (b) What is the hybridization of the nitrogen?arrow_forwardIdentify the electron geometry about each charged atom. Where appropriate, indicate the molecular geometry and approximate bond angle as well. (a) (b) (c) (d) CH3 (e) (f) O `NH H3CN-CH3 CH3arrow_forward
- Draw a Lewis Structure for each of the following species and assign formal charge where appropriate. Using electronegative values from the period table that was provided identify polar covalent bonds and label the atoms δ+ and δ−. For each of the molecules indicate whether or not it has a dipole moment. (a)CH5N (b) HCN (c) H2CO (d) CH3NC(e) CH3SOCH3 (f) H6BNarrow_forwardConsider the Lewis structure shown below.(a) Does the Lewis structure depict a neutral molecule or anion? If it is an ion, what is the charge on the ion? (b) What hybridizationis exhibited by each of the carbon atoms? (c) Arethere multiple equivalent resonance structures for the species?(d) How many electrons are in the p system of the species?arrow_forwardCompute the formal charge (FC) on each atom in the following structures. (b) The hydronium ion, H3O+arrow_forward
- Answer in detailarrow_forwardThe following is a skeleton of a molecular anion having the overall formula C7H6NO–. The H atoms are not shown. Starting with the structure drawn below, complete the Lewis structure by adding all H atoms, valence electrons, and π bonds. This structure will have a –1 formal charge on the oxygen.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_forward
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