Chemistry & Chemical Reactivity
10th Edition
ISBN: 9781337399074
Author: John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 9, Problem 48GQ
The 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 σ bonds and π 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.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
In ozone, O3, the two oxygen atoms on the ends of the molecule are equivalent to one another. (a)What is the best choice of hybridization scheme for the atoms of ozone? (b) For one of the resonance forms of ozone, which of the orbitals are used to make bonds and which are used to hold nonbonding pairs of electrons? (c) Which of the orbitals can be used to delocalize the π electrons? (d) How many electrons are delocalized in the π system of ozone?
Butadiene, C4H6, is a planar molecule that has the followingcarbon–carbon bond lengths:
(a) Predict the bond angles around each of the carbon atoms and sketch the molecule. (b) From left to right, what is the hybridization of each carbon atom in butadiene? (c) The middle C—C bond length in butadiene (1.48 Å) is a little shorter than the average C—C single bond length (1.54 Å). Does this imply that the middle C—C bond in butadiene is weaker or stronger than the average C—C single bond? (d) Based on your answer for part (c), discuss what additional aspects of bonding in butadiene might support the shorter middle C—C bond.
A useful solvent that will dissolve salts as well as organic compounds is the compound acetonitrile, H3CCN. It is present in paint strippers.(a) Write the Lewis structure for acetonitrile, and indicate the direction of the dipole moment in the molecule.(b) Identify the hybrid orbitals used by the carbon atoms in the molecule to form σ bonds.(c) Describe the atomic orbitals that form the π bonds in the molecule. Note that it is not necessary to hybridize the nitrogen atom.
Chapter 9 Solutions
Chemistry & Chemical Reactivity
Ch. 9.1 - Use valence bond theory to describe the bonding in...Ch. 9.1 - Identify the hybridization of each underlined atom...Ch. 9.1 - Use valence bond theory to describe the bonding in...Ch. 9.2 - What is the electron configuration of the H2+ ion?...Ch. 9.2 - Could the anion Li2 exist? What is the ions bond...Ch. 9.2 - The cations O2+ and N2+ are formed when molecules...Ch. 9.3 - Photoelectron spectroscopy is s1milar to the...Ch. 9.3 - What is the energy of a photon with a wavelength...Ch. 9.3 - Using the accompanying figure, state which...Ch. 9.3 - The kinetic energy of an electron ejected from the...
Ch. 9.3 - The N2+ ions that are formed when electrons with...Ch. 9.3 - What is the empirical formula of Tynan purple?Ch. 9.3 - Butter yellow absorbs light with a wavelength of...Ch. 9.3 - Prob. 2.3ACPCh. 9 - Draw the Lewis structure for chloroform, CHCl3....Ch. 9 - Draw the Lewis structure for NF3. What are its...Ch. 9 - Draw the Lewis structure for hydroxylamine, H2NOH....Ch. 9 - Draw the Lewis structure for 1,...Ch. 9 - Draw the Lewis structure for carbonyl fluoride,...Ch. 9 - Draw the Lewis structure for acetamide, CH3CONH2....Ch. 9 - Specify the electron-pair and molecular geometry...Ch. 9 - Specify the electron-pair and molecular geometry...Ch. 9 - Prob. 9PSCh. 9 - What is the hybrid orbital set used by each of the...Ch. 9 - Draw the Lewis structures of the acid HPO2F2 and...Ch. 9 - Draw the Lewis structures of the arid HSO3F and...Ch. 9 - What is the hybridization of the carbon atom in...Ch. 9 - What is the hybridization of the carbon atoms in...Ch. 9 - What is the electron-pair and molecular geometry...Ch. 9 - What is the electron-pair and molecular geometry...Ch. 9 - Prob. 17PSCh. 9 - For each compound below, decide whether cis and...Ch. 9 - Molecular Orbital Theory (See Examples 9.49.6.)...Ch. 9 - Give the electron configurations for the ions Li2+...Ch. 9 - Calcium carbide, CaC2, contains the acetylide ion,...Ch. 9 - Platinum hexafluoride is an extremely strong...Ch. 9 - When sodium and oxygen react, one of the products...Ch. 9 - When potassium and oxygen react, one of the...Ch. 9 - Among the following, which has the shortest bond...Ch. 9 - Consider the following list of small molecules and...Ch. 9 - Prob. 27PSCh. 9 - The nitrosyl ion. NO+, has an interesting...Ch. 9 - These questions are not designated as to type or...Ch. 9 - What is the OSO angle and the hybrid orbital set...Ch. 9 - Sketch the resonance structures for the nitrite...Ch. 9 - Sketch the resonance structures for the nitrate...Ch. 9 - Sketch the resonance structures for the N2O...Ch. 9 - Compare the structure and bonding in CO2 and CO32...Ch. 9 - Numerous molecules are detected in deep space....Ch. 9 - Acrolein, a component of photochemical smog, has a...Ch. 9 - The organic compound below is a member of a class...Ch. 9 - The compound sketched below is acetylsalicylic...Ch. 9 - Phosphoserine is a less-common amino acid. (a)...Ch. 9 - Lactic acid is a natural compound found in sour...Ch. 9 - Cinnamaldehyde ocaus naturally in cinnamon oil....Ch. 9 - The ion Si2 was reported in a laboratory...Ch. 9 - The simple valence bond picture of O2 does not...Ch. 9 - Nitrogen, N2, can ionize to form N2+ or add an...Ch. 9 - Which of the homonuclear, diatomic molecules of...Ch. 9 - Which of the following molecules or ions are...Ch. 9 - Prob. 47GQCh. 9 - The structure of amphetamine, a stimulant, is...Ch. 9 - Menthol is used in soaps, perfumes, and foods. It...Ch. 9 - Prob. 50GQCh. 9 - Suppose you carry out the following reaction of...Ch. 9 - Ethylene oxide is an intermediate in the...Ch. 9 - The sulfamate ion, H2NSO3, can be thought of as...Ch. 9 - The compound whose structure is shown here is...Ch. 9 - Prob. 55ILCh. 9 - Carbon dioxide (CO2), dinitrogen monoxide (N2O),...Ch. 9 - Draw the two resonance structures that describe...Ch. 9 - Draw a Lewis structure for diimide, HNNH. Then,...Ch. 9 - Prob. 59SCQCh. 9 - Consider the three fluorides BF4, SiF4, and SF4....Ch. 9 - When two amino acids react with each other, they...Ch. 9 - What is the connection between bond order, bond...Ch. 9 - When is it desirable to use MO theory rather than...Ch. 9 - Show how valence bond theory and molecular orbital...Ch. 9 - Three of the four molecular orbitals for...Ch. 9 - Lets look more closely at the process of...Ch. 9 - Borax has the molecular formula Na2B4O5(OH)4. The...Ch. 9 - A model of the organic compound allene is shown...Ch. 9 - Prob. 69SCQCh. 9 - Prob. 70SCQCh. 9 - Bromine forms a number of oxides of varying...Ch. 9 - Prob. 72SCQCh. 9 - Urea reacts with malonic acid to produce...
Knowledge Booster
Learn more about
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
- Aspirin, or acetylsalicylic acid, has the formula C9H8O4 and the skeleton structure (a) Complete the Lewis structure and give the number of bonds and bonds in aspirin. (b) What is the hybridization about the CO2H carbon atom (colored blue)? (c) What is the hybridization about the carbon atom in the benzene-like ring that is bonded to an oxygen atom (colored red)? Also, what is the hybridization of the oxygen atom bonded to this carbon atom?arrow_forwardThe sulfamate ion, H2NSO3, can be thought of as having been formed from the amide ion, NH2, and sulphur trioxide, SO3. (a) What are the electron-pair and molecular geometries or the amide ion and or SO3? What are the hybridizations of the N and S atoms, respectively? (b) Sketch a structure for the sulfamate ion, and estimate the bond angles. (c) What changes in hybridization do you expect for N and S in the course of the reaction NH2 + SO3 H2NSO3? (d) Is SO3 the donor of an electron pair or the acceptor of an electron pair in the reaction with amide ion? Does the electrostatic potential map shown below confirm your prediction?arrow_forwardTryptophan is one of the amino acids found in proteins:(a) What is the hybridization of each of the numbered C, N, andO atoms? (b) How many bonds are present in tryptophan? (c) Predict the bond angles at points a, b, and c.arrow_forward
- Acetylsalicylic acid, better known as aspirin, has the Lewisstructure (a) What are the approximate values of the bond angles labeled1, 2, and 3? (b) What hybrid orbitals are used about thecentral atom of each of these angles? (c) How many s bondsare in the molecule?arrow_forwardThe compound 2,6-dimethylpyrazine (below) gives chocolate its odor and is used in flavorings. (a) Which atomic orbitals mix to form the hybrid orbitals of N? (b) In what type of hybrid orbital do the lone pairs of N reside? (c) Is C in CH3 hybridized the same as any C in the ring? Explain.arrow_forward(a) State the hybrid orbitals for C1,C2,O1 and O2 (b) state the number of π bonds present (c) State teh number of C atoms with sp2 hybridization.arrow_forward
- In the hydrocarbon: (a) What is the hybridization at each carbon atom in themolecule? (b) How many σ bonds are there in the molecule?(c) How many π bonds? (d) Identify all the 120° bond anglesin the molecule.arrow_forward(a) What is the hybridization of chlorine in Clo4 ? (Type your answer using the format sp3 for sp3.) (b) What is the hybridization of bromine in BrF5? (c) What is the hybridization of bromine in BrO2 ?arrow_forwardThe compound 2,6-dimethylpyrazine(below)gives choco-late its odor and is used in flavorings.(a) Which atomic orbitals mix to form the hybrid orbitals of N? (b) In what type of hybrid orbital do the lone pairs of N reside? (c) Is C in CH₃ hy-bridized the same as any C in the ring? Explain.arrow_forward
- Butadiene, C4H6, is a planar molecule that has the followingcarbon–carbon bond lengths:(a) Predict the bond angles around each of the carbon atomsand sketch the molecule. (b) From left to right, whatis the hybridization of each carbon atom in butadiene?(c) The middle C¬C bond length in butadiene (1.48 Å) isa little shorter than the average C¬C single bond length(1.54 Å). Does this imply that the middle C¬C bond in butadieneis weaker or stronger than the average C¬C singlebond? (d) Based on your answer for part (c), discuss what additional aspects of bonding in butadiene might supportthe shorter middle C¬C bond.arrow_forwardIsoniazid (below) is an antibacterial agent that is effective against many common strains of tuberculosis. (a) How many σ bonds are in the molecule? (b) What is the hybridization of each C and N atom?arrow_forwardIn hydrogen isocyanide molecules (HCN), both carbon (C: 1s^2 2s^2 2p^2 ) and nitrogen (N: 1s^2 2s^2 2p^3 ) atoms undergo sp hybridization. (a) Use Orbital Hybridization theory to determine the molecular shape of HCN molecules. (b) Explain how the C atom binds to the N atom in HCN molecules.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Chemistry & Chemical ReactivityChemistryISBN:9781133949640Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Chemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage Learning
Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry: Principles and Practice
Chemistry
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Stoichiometry - Chemistry for Massive Creatures: Crash Course Chemistry #6; Author: Crash Course;https://www.youtube.com/watch?v=UL1jmJaUkaQ;License: Standard YouTube License, CC-BY
Bonding (Ionic, Covalent & Metallic) - GCSE Chemistry; Author: Science Shorts;https://www.youtube.com/watch?v=p9MA6Od-zBA;License: Standard YouTube License, CC-BY
General Chemistry 1A. Lecture 12. Two Theories of Bonding.; Author: UCI Open;https://www.youtube.com/watch?v=dLTlL9Z1bh0;License: CC-BY