Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 9.9D, Problem 9.14P
In the addition of just 1 mole of bromine to 1 mole of hex-1-yne, should the hex-1-yne be added to a bromine solution or should the bromine be added to the hex-1-yne? Explain your answer.
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When 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1-
butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the
product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for
70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium
propoxide were the base?
base
Br
A.
Less than 45%
B.
C.
45%
Between 45% and 70%
D.
More than 70%
Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the
major product.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• If more than one structure fits the description, draw them all.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Separate structures with + signs from the drop-down menu.
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ChemDoodleⓇ
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Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the
major product.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• If more than one structure fits the description, draw them all.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Separate structures with + signs from the drop-down menu.
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ChemDoodle
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Chapter 9 Solutions
Organic Chemistry (9th Edition)
Ch. 9.1 - a. Count the elements of unsaturation in...Ch. 9.2 - Prob. 9.2PCh. 9.4B - What reaction would acetylene likely undergo if it...Ch. 9.6 - Prob. 9.4PCh. 9.6 - Predict the products of the following acid-base...Ch. 9.7A - Solved Problem9-1 showed the synthesis of...Ch. 9.7A - Show how you might synthesize the following...Ch. 9.7B - Prob. 9.8PCh. 9.7B - Show how you would synthesize...Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...
Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...Ch. 9.9C - Show how you would convert a. oct-3-yne to...Ch. 9.9C - The fragrance of (Z)-1-phenylhex-2-en-1-ol...Ch. 9.9D - In the addition of just 1 mole of bromine to 1...Ch. 9.9E - Propose a mechanism for the entire reaction of...Ch. 9.9E - Predict the major product(s) of the following...Ch. 9.9E - Propose a mechanism for the reaction of pent-1-yne...Ch. 9.9E - Show how hex-1-yne might be converted to a....Ch. 9.9F - When pent-2-yne reacts with mercuric sulfate in...Ch. 9.9F - Prob. 9.20PCh. 9.9F - Prob. 9.21PCh. 9.9F - Prob. 9.22PCh. 9.10A - Predict the product(s) you would expect from...Ch. 9.10B - Prob. 9.24PCh. 9.10B - Prob. 9.25PCh. 9 - Prob. 9.26SPCh. 9 - Give common names for the following compounds. a....Ch. 9 - Prob. 9.28SPCh. 9 - Prob. 9.29SPCh. 9 - Using cyclooctyne as your starting material, show...Ch. 9 - Prob. 9.31SPCh. 9 - Prob. 9.32SPCh. 9 - Predict the products of reaction of pent-1-yne...Ch. 9 - Show how you would accomplish the following...Ch. 9 - Show how you would synthesize the following...Ch. 9 - Predict the products formed when CH3CH2C C : Na+...Ch. 9 - Prob. 9.37SPCh. 9 - Prob. 9.38SPCh. 9 - When compound Z is treated with ozone, followed by...Ch. 9 - Show how you would convert the following starting...Ch. 9 - The following functional-group interchange is a...Ch. 9 - Using any necessary inorganic reagents, show how...Ch. 9 - Prob. 9.43SP
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- write acid-base reactions using NaOH/HCI and your acidic/basic compound (benzoic acid/p-toluidine). Is your neutral compound (9-fluorenone) acid/base reactive? explainarrow_forwardDraw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. ● If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● ● ✓ ? ChemDoodleⓇ n [ ]#arrow_forwardGiven the data, find the specific heat of part A; Heat of Reaction 1 (ΔH1) of part B; Heat of Reaction 2 (ΔH2) of part C; Heat of Reaction 3 (ΔH3) of part D .arrow_forward
- Lithium diorganocopper (Gilman) reagents are prepared by treatment of an organolithium compound with copper(I) iodide. Decide what lithium diorganocopper (Gilman) reagent is needed to convert 1-bromopropane into 1-pentene. Draw the structure of the organolithium compound that is used to prepare this Gilman reagent in the box below.arrow_forwardComplete the following reaction schemes by choosing the correct product, starting material, and/or reagent from the selection below. Your answer should simply be the number that represents your choice. For example, if you believe that the correct answer is the structure represented by the 3, then enter 3 into the correct answer box. Also, answer any additional questions that might be included with a reaction scheme(s). H₂C 0 1. NaNH, 1. NaNH, 2. CH₂CH₂CH₂Br 2. CH₂CH₂Br OH 1 4 3 2 5 O 6 Naº NH3 (1) 11 OH 7 7 XXXXXXXXX E RUTINE H H₂ Pd/C, CaCO3 8 1. NaNHz 2. CH₂(CH₂)₂CH₂Br 13 MCPBA 12 A B a. What reagent(s) is/are required for reaction A to proceed as drawn? What reagent(s) is/are required for reaction B to proceed as drawn? H₂C 9 H₂ Pd/C 14 -0 CH3 Br 10 1. BH-THF 2. H,O2, HỌ, H,O 15arrow_forward6- In a 1H-NMR spectra on a scale of 0 – 10 ppm, Show the exact locations in ppm of 1-the saturated hydrocarbons, 2- the unsaturated hydrocarbons, 3- the halogenatedhydrocarbons and 4- the aromatic hydrocarbons.arrow_forward
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