Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 1.13, Problem 34P
a. What are the relative lengths and strengths of the bonds in Cl2 and Br2?
b. What are the relative lengths and strengths of the carbon-halogen bonds in CH3F, CH3Cl, and CH3Br?
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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 1 Solutions
Organic Chemistry
Ch. 1.1 - Oxygen has three isotopes, 16O, 17O, and 18O. The...Ch. 1.1 - Chlorine has two isotopes, 35Cl and 37Cl; 75.77%...Ch. 1.2 - Prob. 3PCh. 1.2 - a. Write the ground-state electronic configuration...Ch. 1.2 - Look at the relative positions of each pair of...Ch. 1.3 - a. Find potassium (K) in the periodic table and...Ch. 1.3 - Which bond is more polar? a. b. c. d.Ch. 1.3 - Which of the following has a. the most polar bond?...Ch. 1.3 - Use the symbols + and to show the direction of...Ch. 1.3 - Explain why HCL has a smaller dipole moment than...
Ch. 1.3 - After examining the potential maps for LiH, HF,...Ch. 1.4 - An atom with a formal charge does not necessarily...Ch. 1.4 - Prob. 15PCh. 1.4 - a. Draw two Lewis structure for C2H6O. b. Draw...Ch. 1.4 - Draw the lone-pair electrons that are not shown in...Ch. 1.4 - Prob. 19PCh. 1.4 - Which of the atoms in the molecular models in...Ch. 1.4 - Prob. 21PCh. 1.5 - Draw the following orbitals: a. 3s orbital b. 4s...Ch. 1.6 - Prob. 23PCh. 1.6 - Indicate the kind of molecular orbital (, , , or )...Ch. 1.7 - What orbitals are used to form the 10 sigma bonds...Ch. 1.7 - Explain why a bond formed by overlap of s orbital...Ch. 1.9 - Put n number in each of the blanks: a. __ s...Ch. 1.11 - Predict the approximate bond angles in a. the...Ch. 1.11 - According to the potential map for the ammonium...Ch. 1.12 - Prob. 32PCh. 1.13 - a. What are the relative lengths and strengths of...Ch. 1.13 - Prob. 35PCh. 1.14 - Prob. 36PCh. 1.15 - Which of the bond in a carbon-oxygen double bond...Ch. 1.15 - Would you expect a CC bond formed by sp2sp2...Ch. 1.15 - Caffeine is a natural insecticide found in the...Ch. 1.15 - Prob. 41PCh. 1.15 - Predict the approximate bond angles for a. the CNC...Ch. 1.16 - If the dipole moment of CH3F is 1.847 D and the...Ch. 1.16 - Account for the difference in the shape and color...Ch. 1.16 - What of the following molecules would you expect...Ch. 1 - Prob. 46PCh. 1 - Prob. 47PCh. 1 - What is the hybridization of all the atoms (other...Ch. 1 - Draw the condensed structure of a compound that...Ch. 1 - Predict the approximate bond angles: a. the CNH...Ch. 1 - Prob. 51PCh. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - 53. What is the hybridization of each of the...Ch. 1 - Rank the bonds from most polar. a. CO, CF, CN b....Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - What is the hybridization of the indicated atom in...Ch. 1 - Prob. 57PCh. 1 - Prob. 58PCh. 1 - Draw the missing lone-pair electrons and assigns...Ch. 1 - a. Which of the indicated bonds in each molecule...Ch. 1 - For each of the following molecules, indicate the...Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Rank the following compounds from highest dipole...Ch. 1 - In which orbitals are the lone pairs in nicotine?Ch. 1 - Prob. 65PCh. 1 - Prob. 66PCh. 1 - a. Which of the species have bond angles of 109.5?...Ch. 1 - Prob. 68PCh. 1 - Which compound has a larger dipole moment: CH3Cl...Ch. 1 - Prob. 70PCh. 1 - Prob. 71PCh. 1 - Explain why CH3Cl has a greater dipole moment than...Ch. 1 - Prob. 73P
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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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