Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Textbook Question
Chapter 1.SE, Problem 47AP
Allene, H2C=C=CH2, is somewhat unusual in that it has two adjacent double bonds. Draw a picture showing the orbitals involved in the σ and π bonds of allene. Is the central carbon atom sp2- or sp-hybridized? What about the hybridization of the terminal carbons? What shape do you predict for allene?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Draw a line-bond structure for propene, CH3CH=CH2. Indicate the hybridization of the orbitals on each carbon, and predict the value of each bond angle.
What is the hybridization of the sigma bonding orbitals of the carbon atom?
Allene (1,2-propadiene), H2C=C=CH2, has two adjacent double bonds. What kind of hybridization must the central carbon have? Sketch the bonding π orbitals in allene.What shape do you predict for allene?
Chapter 1 Solutions
Organic Chemistry
Ch. 1.3 - Give the ground-state electron configuration for...Ch. 1.3 - How many electrons does each of the following...Ch. 1.4 - Prob. 3PCh. 1.4 - Convert the following representation of ethane,...Ch. 1.4 - What are likely formulas for the following...Ch. 1.4 - Prob. 6PCh. 1.4 - Prob. 7PCh. 1.7 - Draw a line-bond structure for propane, CH3CH2CH3....Ch. 1.7 - Convert the following molecular model of hexane, a...Ch. 1.8 - Draw a line-bond structure for propene, CH3CH=CH2....
Ch. 1.8 - Draw a line-bond structure for 1, 3-butadiene,...Ch. 1.8 - Following is a molecular model of aspirin...Ch. 1.9 - Draw a line-bond structure for propyne, CH3C≡CH....Ch. 1.10 - Prob. 14PCh. 1.12 - Prob. 15PCh. 1.12 - Prob. 16PCh. 1.12 - The following molecular model is a representation...Ch. 1.SE - Convert each of the following molecular models...Ch. 1.SE - The following model is a representation of citric...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - How many valence electrons does each of the...Ch. 1.SE - Give the ground-state electron configuration for...Ch. 1.SE - Prob. 24APCh. 1.SE - Prob. 25APCh. 1.SE - Draw an electron-dot structure for acetonitrile,...Ch. 1.SE - Draw a line-bond structure for vinyl chloride,...Ch. 1.SE - Fill in any nonbonding valence electrons that are...Ch. 1.SE - Convert the following line-bond structures into...Ch. 1.SE - Convert the following molecular formulas into...Ch. 1.SE - Prob. 31APCh. 1.SE - Oxaloacetic acid, an important intermediate in...Ch. 1.SE - Prob. 33APCh. 1.SE - Potassium methoxide, KOCH3, contains both covalent...Ch. 1.SE - What is the hybridization of each carbon atom in...Ch. 1.SE - Prob. 36APCh. 1.SE - Prob. 37APCh. 1.SE - What bond angles do you expect for each of the...Ch. 1.SE - Propose structures for molecules that meet the...Ch. 1.SE - What kind of hybridization do you expect for each...Ch. 1.SE - Pyridoxal phosphate, a close relative of vitamin...Ch. 1.SE - Prob. 42APCh. 1.SE - Prob. 43APCh. 1.SE - Quetiapine, marketed as Seroquel, is a heavily...Ch. 1.SE - Tell the number of hydrogens bonded to each carbon...Ch. 1.SE - Why do you suppose no one has ever been able to...Ch. 1.SE - Allene, H2C=C=CH2, is somewhat unusual in that it...Ch. 1.SE - Allene (see Problem 1-47) is structurally related...Ch. 1.SE - Complete the electron-dot structure of caffeine,...Ch. 1.SE - Most stable organic species have tetravalent...Ch. 1.SE - A carbanion is a species that contains a...Ch. 1.SE - Divalent carbon species called carbenes are...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - Prob. 56APCh. 1.SE - Among the most common over-the-counter drugs you...
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_forwardGamma hydroxybutyric acid, GHB, infamous as a date rape drug, is used illicitly because of its effects on the nervous system. The condensed molecular formula for GHB is HO(CH2)3COOH. (a) Write the Lewis structure for GHB. (b) Identify the hybridization of the carbon atom in the CH2 groups and of the terminal carbon. (c) Is hydrogen bonding possible in GHB? If so, write Lewis structures to illustrate the hydrogen bonding. (d) Which carbon atoms are involved in sigma bonds? In pi bonds? (e) Which oxygen atom is involved in sigma bonds? In pi bonds?arrow_forwardThere are two compounds with the molecular formula HN3. One is called hydrogen azide; the other is cyclotriazene. (a) Write the Lewis structure for each compound. (b) Designate the hybridization of each nitrogen in hydrogen azide. (c) What is the hybridization of each nitrogen in cyclotriazene? (d) How many sigma bonds are in hydrogen azide? In cyclotriazene? (e) How many pi bonds are in hydrogen azide? In cyclotriazene? (f) Give approximate values for the N-to-N-to-N bond angles in each molecule.arrow_forward
- Draw the Lewis structure for 1, 1-dimethylhydrazine [(CH3)2NNH2, a compound used as a rocket fuel]. What: is the hybridization for the two nitrogen atoms in this molecule? What orbitals overlap to form the bond between the nitrogen atoms?arrow_forwardCinnamaldehyde ocaus naturally in cinnamon oil. (a) What is the most polar bond in the molecule? (b) How many bonds and how many bonds are there? (c) Is cis-trans isomerism possible? If so, draw the isomers of the molecule. (d) Give the hybridization of the C atoms in the molecule. (e) What are the values of the bond angles 1, 2, and 3 ?arrow_forwardIn Chapter 6, we study a group of organic cations called carbocations. Following is the structure of one such carbocation, the tert-butyl cation. (a) How many electrons are in the valence shell of the carbon bearing the positive charge? (b) Using VSEPR, predict the bond angles about this carbon. (c) Given the bond angle you predicted in (b), what hybridization do you predict for this carbon?arrow_forward
- 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 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_forwardPhosphoserine is a less-common amino acid. (a) Identify the hybridizations of atoms I through 5. (b) What are the approximate values of the bond angles A, B. C, and D? (c) What are the most polar bonds in the molecule?arrow_forwardExplain how the dipole moment could be used to distinguish between the cis and trans isomers of 1,2-dibromoethene:arrow_forward
- нн H H а С—Сь H2 H-Ć-Č–H b + a H Many reactions involve a change in hybridization of one or more atoms in the starting material. In this reaction, determine the hybridization of the indicated atoms in the organic starting material, and determine if they have changed hybridization during the reaction. Atom a: Reactant: Product: Atom b: Reactant: Product:arrow_forwardPlease send me the question in 20 minutes it's very urgent plzarrow_forwardWhat is the orbital hybridization of each carbon in the following: O ║ CH3–C≡C-CH2–C–CHBr-CH3arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage LearningChemistry: An Atoms First ApproachChemistryISBN:9781305079243Author:Steven S. Zumdahl, Susan A. ZumdahlPublisher:Cengage Learning
- Chemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage LearningChemistry & Chemical ReactivityChemistryISBN:9781133949640Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage LearningChemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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: An Atoms First Approach
Chemistry
ISBN:9781305079243
Author:Steven S. Zumdahl, Susan A. Zumdahl
Publisher: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: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Linear Combination of Atomic Orbitals LCAO; Author: Edmerls;https://www.youtube.com/watch?v=nq1zwrAIr4c;License: Standard YouTube License, CC-BY
Quantum Molecular Orbital Theory (PChem Lecture: LCAO and gerade ungerade orbitals); Author: Prof Melko;https://www.youtube.com/watch?v=l59CGEstSGU;License: Standard YouTube License, CC-BY