Organic Chemistry - With Access (Looseleaf) (Custom)
4th Edition
ISBN: 9781259726224
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 1, Problem 1.80P
The principles of this chapter can be applied to organic molecules of any size. Answer the following questions about amoxicillin, an antibiotic from the penicillin family.
a. Predict the hybridization and geometry d. How many
around each indicated atom. Label them.
b. Label five polar bonds using the e. Find a
symbols
c. Draw the skeletal structure.
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2) a) Consider the following molecule . Given what you have learned about hybridization theory, draw an image or images explaining the bonding situation in this molecule. I want you to draw out all of the orbitals, hybrid orbitals and how they overlap to form the bonds in the molecule. Indicate the % s or p character in the given atomic and hybrid orbitals. Which C-C bond or bonds are the longest? In a paragraph or so explain the image or images you just drew.
b) Lastly, consider the molecule below. Indicate the Molecular formula, the molar mass, label the hybridization of each atom except for hydrogen, indicate any chiral centers with a *, which bond or bonds are the shortest, identify by name of each functional group with an arrow pointing to the group.
a) Consider a molecule of acetone cyanohydrin, shown below. What is the hybridization and molecular geometry at CA, CB, and O?
(b) For Carbon B (CB) and nitrogen (N), draw orbital energy diagrams showing the orbitals involved in bonding after hybridization. Be sure to fill the orbitals appropriately with valence electrons.
c) In your diagrams in part (b), which orbitals are involved in sigma and pi bonding?
Orbitals Involved in Sigma Bonding Orbitals Involved in Pi Bonding
2p
sp
sp2
sp3
2p
sp
sp2
sp3
(d) In a sample containing many molecules of acetone cyanohydrin (and no other substances), what type(s) of intermolecular forces could be present? Choose all that apply. Covalent Bonds Hydrogen Bonds Dipole-Dipole Forces London Dispersion Forces
Chapter 1 Solutions
Organic Chemistry - With Access (Looseleaf) (Custom)
Ch. 1 - While the most common isotope of nitrogen has a...Ch. 1 - Label each bond in the following compounds as...Ch. 1 - How many covalent bonds are predicted for each...Ch. 1 - Draw a valid Lewis structure for each species. a....Ch. 1 - Draw an acceptable Lewis structure for each...Ch. 1 - Prob. 1.6PCh. 1 - Draw a Lewis structure for each ion. a. CH3Ob....Ch. 1 - Draw Lewis structures for each molecular formula....Ch. 1 - Prob. 1.9PCh. 1 - Prob. 1.10P
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Draw a second resonance structure for each...Ch. 1 - Prob. 1.14PCh. 1 - Draw a second resonance structure for nitrous...Ch. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Simplify each condensed structure by using...Ch. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Convert each skeletal structure to a complete...Ch. 1 - Draw in all hydrogens and lone pairs on the...Ch. 1 - Prob. 1.26PCh. 1 - What orbitals are used to form each of the CC, and...Ch. 1 - What orbitals are used to form each bond in the...Ch. 1 - Determine the hybridization around the highlighted...Ch. 1 - Classify each bond in the following molecules as ...Ch. 1 - Prob. 1.31PCh. 1 - Rank the following atoms in order of increasing...Ch. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Provide the following information about...Ch. 1 - Use the ball-and-stick model to answer each...Ch. 1 - Citric acid is responsible for the tartness of...Ch. 1 - Zingerone gives ginger its pungent taste. a.What...Ch. 1 - Two radioactive isotopes of iodine used for the...Ch. 1 - Prob. 1.40PCh. 1 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each N and O atom in the...Ch. 1 - Draw one valid Lewis structure for each compound....Ch. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Draw all reasonable resonance structures for each...Ch. 1 - Prob. 1.56PCh. 1 - Rank the resonance structures in each group in...Ch. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - Predict the geometry around each indicated atom....Ch. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Each of the following condensed or skeletal...Ch. 1 - Prob. 1.69PCh. 1 - Prob. 1.70PCh. 1 - Prob. 1.71PCh. 1 - Prob. 1.72PCh. 1 - Prob. 1.73PCh. 1 - Prob. 1.74PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Label the polar bonds in each molecule. Indicate...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.79PCh. 1 - The principles of this chapter can be applied to...Ch. 1 -
a. What is the hybridization of each N atom in...Ch. 1 - 1.77 Stalevo is the trade name for a medication...Ch. 1 - 1.78 and are two highly reactive carbon...Ch. 1 - 1.79 The N atom in (acetamide) is hybridized,...Ch. 1 - Prob. 1.85PCh. 1 - Prob. 1.86PCh. 1 - Prob. 1.87PCh. 1 - Prob. 1.88PCh. 1 - Prob. 1.89PCh. 1 - Prob. 1.90P
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- Consider acetyl salicylic acid, better known as aspirin. Its structure is (a) How many sigma and pi bonds are there in aspirin? (b) What are the approximate values of the angles marked (in blue) A, B, and C? (c) What is the hybridization of each atom marked (in red) 1, 2, and 3?arrow_forwardPredict the valence electron molecular orbital configurations for the following, and state whether they will be stable or unstable ions. (a) Na,2+ (b) Mg,2 (c) AI,2 (d) Si,2 (e) p2+ (f) s,2 (g) F,2 (h) Ar,2 40. Predict the valence electron molecular orbital configurations for the following, and state whether they will be stable or unstable ions. (a) Na22+ (b) Mg22+ (c) Al22+ (d) Si22+ (e) P22+ (f) S22+ (g) F22+ (h) Ar22+arrow_forwardConsider three molecules: A, B, and C. Molecule A has a hybridization of sp3 Molecule B has two more effective pairs (electron pairs around the central atom) than molecule A. Molecule C consists of two bonds and two bonds. Give the molecular structure, hybridization, bond angles, and an example for each molecule.arrow_forward
- For each of the following molecules, state the bond angle (or bond angles, as appropriate) that you would expect to see on the central atom based on the simple VSEPR model. Would you expect the actual bond angles to be greater or less than this? a CCl4 b SCl2 c COCl2 d AsH3arrow_forwardThe structure of amphetamine, a stimulant, is shown below. (Replacing one H atom on the NH2, or amino, group with CH3 gives methamphetamine a particularly dangerous drug commonly known as speed.) (a) What are the hybrid orbitals used by the C atoms of the C6 ring. by the C atoms of the side chain, and by the N atom? (b) Give approximate values for the bond angles A, B, and C. (c) How many bonds and bonds are in the molerule? (d) Is the molecule polar or nonpolar? (e) Amphetamine reacts readily with a proton (H+) in aqueous solution. Where does this proton attach to the molecule? Explain how the electrostatic potential map predicts this site of protonation.arrow_forwardAllene (1,2-propadicne), a gas, has the following structure: What is the hybridization at each carbon atom? What is the geometry about each carbon atom? Using valencebond theory, describe the bonding about the center carbon atom. 1,3-dichloroallene is a derivative of allene with the following structure: Is this a polar molecule? (If you have difficulty visualizing the structure of this molecule, you might build a molecular model of it.)arrow_forward
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