OWLv2 with MindTap Reader, 4 terms (24 months) Printed Access Card for Zumdahl/Zumdahl's Chemistry, 9th
9th Edition
ISBN: 9781285185446
Author: Steven S. Zumdahl, Susan A. Zumdahl
Publisher: Cengage Learning
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Textbook Question
Chapter 9, Problem 18E
Use the localized electron model to describe the bonding in CCl4.
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Consider the following nucleophilic substitution reaction. The compound listed above the arrow is the solvent for the reaction. If nothing is listed over the arrow,
then the nucleophile is also the solvent for the reaction.
Part 1 of 2
Br
CH,CN
+ I¯
What is the correct mechanism for the reaction? Select the single best answer.
@SN2
○ SN 1
Part: 1/2
Part 2 of 2
Draw the products for the reaction. Include both the major organic product and the inorganic product. If more than one stereoisomer is possible, draw
only one stereoisomer. Include stereochemistry where relevant.
Click and drag to start drawing a
structure.
X
હૈ
20.33 Think-Pair-Share
(a) Rank the following dienes and dienophiles in order of increasing reactivity in the
Diels-Alder reaction.
(i)
CO₂Et
(ii)
COEt
||
CO₂Et
MeO
MeO
(b) Draw the product that results from the most reactive diene and most reactive
dienophile shown in part (a).
(c) Draw a depiction of the orbital overlap involved in the pericyclic reaction that oc-
curs between the diene and dienophile in part (b).
(d) Is the major product formed in part (b) the endo or exo configuration? Explain
your reasoning.
20.40 The following compound undergoes an intramolecular Diels-Alder reaction to give a
tricyclic product. Propose a structural formula for the product.
CN
heat
An intramolecular
Diels-Alder adduct
Chapter 9 Solutions
OWLv2 with MindTap Reader, 4 terms (24 months) Printed Access Card for Zumdahl/Zumdahl's Chemistry, 9th
Ch. 9 - Why do we hybtidize atomic orbitals to explain the...Ch. 9 - What hybridization is required for central atoms...Ch. 9 - Describe the bonding in H2S, CH4, H2CO and HCN...Ch. 9 - What hybridization is required for central atoms...Ch. 9 - Electrons in bonding molecular orbitals are most...Ch. 9 - What are molecular orbitals? How do they compare...Ch. 9 - Explain the difference between the and MOs for...Ch. 9 - Compare Figs. 4-47 and 4-49. Why are they...Ch. 9 - Which of the following would you expect to be more...Ch. 9 - Draw the Lewis structure for HCN. Indicate the...
Ch. 9 - Which is the more correct statement: The methane...Ch. 9 - Compare and contrast the MO model with the local...Ch. 9 - What are the relationships among bond order, bond...Ch. 9 - In the hybrid orbital model, compare and contrast ...Ch. 9 - In the molecular orbital mode l, compare and...Ch. 9 - Why are d orbitals sometimes used to form hybrid...Ch. 9 - The atoms in a single bond can rotate about the...Ch. 9 - Compare and contrast bonding molecular orbitals...Ch. 9 - What modification to the molecular orbital model...Ch. 9 - Why does the molecular orbital model do a better...Ch. 9 - The three NO bonds in NO3 are all equivalent in...Ch. 9 - Use the localized electron model to describe the...Ch. 9 - Use the localized electron model to describe the...Ch. 9 - Use the localized electron model to describe the...Ch. 9 - Use the localized electron model to describe the...Ch. 9 - The space-filling models of ethane and ethanol are...Ch. 9 - The space-filling models of hydrogen cyanide and...Ch. 9 - Give the expected hybridization of the central...Ch. 9 - Give the expected hybridization of the central...Ch. 9 - Give the expected hybridization of the central...Ch. 9 - Give the expected hybridization of the central...Ch. 9 - For each of the following molecules, write the...Ch. 9 - For each of the following molecules or ions that...Ch. 9 - Prob. 31ECh. 9 - The allene molecule has the following Lewis...Ch. 9 - Indigo is the dye used in coloring blue jeans. The...Ch. 9 - Urea, a compound formed in the liver, is one of...Ch. 9 - Biacetyl and acetoin are added to margarine to...Ch. 9 - Many important compounds in the chemical industry...Ch. 9 - Two molecules used in the polymer industry are...Ch. 9 - Hot and spicy foods contain molecules that...Ch. 9 - One of the first drugs to be approved for use in...Ch. 9 - The antibiotic thiarubin-A was discovered by...Ch. 9 - Consider the following molecular orbitals formed...Ch. 9 - Sketch the molecular orbital and label its type (...Ch. 9 - Which of the following are predicted by the...Ch. 9 - Which of the following are predicted by the...Ch. 9 - Using the molecular orbital model, write electron...Ch. 9 - Consider the following electron configuration:...Ch. 9 - Using molecular orbital theory, explain why the...Ch. 9 - Using the molecular orbital model to describe the...Ch. 9 - The transport of O2 in the blood is carried out by...Ch. 9 - A Lewis structure obeying the octet rule can be...Ch. 9 - Using the molecular orbital model, write electron...Ch. 9 - Using the molecular orbital model, write electron...Ch. 9 - In which of the following diatomic molecules would...Ch. 9 - In terms of the molecular orbital model, which...Ch. 9 - Show how two 2p atomic orbitals can combine to...Ch. 9 - Show how a hydrogen 1s atomic orbital and a...Ch. 9 - Use Figs. 4-54 and 4-55 to answer the following...Ch. 9 - Acetylene (C2H2) can be produced from the reaction...Ch. 9 - Describe the bonding in NO+, NO, and NO, using...Ch. 9 - Describe the bonding in the O3 molecule and the...Ch. 9 - Describe the bonding in the CO32 ion using the...Ch. 9 - Draw the Lewis structures, predict the molecular...Ch. 9 - FClO2 and F3ClO can both gain a fluoride ion to...Ch. 9 - Two structures can be drawn for cyanuric acid: a....Ch. 9 - Give the expected hybridization for the molecular...Ch. 9 - Vitamin B6 is an organic compound whose deficiency...Ch. 9 - Aspartame is an artificial sweetener marketed...Ch. 9 - Prob. 69AECh. 9 - The three most stable oxides of carbon are carbon...Ch. 9 - Complete the following resonance structures for...Ch. 9 - Prob. 73AECh. 9 - Describe the bonding in the first excited state of...Ch. 9 - Using an MO energy-level diagram, would you expect...Ch. 9 - Show how a dxz. atomic orbital and a pz, atomic...Ch. 9 - What type of molecular orbital would result from...Ch. 9 - Consider three molecules: A, B, and C. Molecule A...Ch. 9 - Draw the Lewis structures for TeCl4, ICl5, PCl5,...Ch. 9 - A variety of chlorine oxide fluorides and related...Ch. 9 - Pelargondin is the molecule responsible for the...Ch. 9 - Complete a Lewis structure for the compound shown...Ch. 9 - Which of the following statements concerning SO2...Ch. 9 - Consider the molecular orbital electron...Ch. 9 - Place the species B2+ , B2, and B2 in order of...Ch. 9 - Consider the following computer-generated model of...Ch. 9 - Cholesterol (C27liu;O) has the following...Ch. 9 - Cyanamide (H2NCN), an important industrial...Ch. 9 - A flask containing gaseous N2 is irradiated with...Ch. 9 - Prob. 92CPCh. 9 - Values of measured bond energies may vary greatly...Ch. 9 - Use the MO model to explain the bonding in BeH2....Ch. 9 - Prob. 95CPCh. 9 - Arrange the following from lowest to highest...Ch. 9 - Use the MO model to determine which of the...Ch. 9 - Given that the ionization energy of F2 is 290...Ch. 9 - Carbon monoxide (CO) forms bonds to a variety of...Ch. 9 - Prob. 100CPCh. 9 - As the bead engineer of your starship in charge of...Ch. 9 - Determine the molecular structure and...
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- What is the reaction mechanism for this?arrow_forwardWhat is the reaction mechanism for this?arrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. + Drawing Arrows CH3ONA, CH3OH heat : Br:O Na → H H Br Na + H H H H H :0: .H + Undo Reset Done Q CH3 Drag To Pan +arrow_forward
- What is the reaction mechanism for this?arrow_forward20.19 Predict the structure of the major 1,2-addition product formed by reaction of one mole of Cl₂ with 3-methylenecyclohexene. Also predict the structure of the 1,4-addition product formed under these conditions. 20.20 Which of the two molecules shown do you expect to be the major product formed by 1,2-addition of HCI to cyclopentadiene? Explain. Cyclopentadiene + HC 3-Chlorocyclopentene (racemic) or 4-Chlorocyclopentene (racemic)arrow_forward20.35 Propose structural formulas for compounds A and B and specify the configuration of compound B. EtO₂C 250°C C14H2004 CO₂Et 1. Oso, then NaHSO3 2. HIO4 C14H2006 A Barrow_forward
- 20.21 Predict the major product formed by 1,4-addition of HCI to cyclopentadiene. 20.22 Draw structural formulas for the two constitutional isomers with the molecular for- mula C₂H,Br, formed by adding one mole of Br, to cyclopentadiene.arrow_forwardAdd substituents to draw the conformer below (sighting down the indicated bond), then rotate the back carbon to provide the conformation that will be capable of an E2 elimination. R/S stereochemistry is graded. + I I H CH3 Ph Досн Br OCH 3 Drawing Q H Atoms, Bonds and Rings Charges Tap a node to see suggestions. H H H H H Undo Reset Remove Done Rotatearrow_forward20.17 Predict the structure of the major product formed by 1,2-addition of HBr to 3-methylenecyclohexene. 3-Methylenecyclohexene 20.18 Predict the major product formed by 1,4-addition of HBr to 3-methylenecyclohexene.arrow_forward
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