Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 14, Problem 14.48SP
(a)
Interpretation Introduction
To determine: The mechanism for the given information of the reaction.
Interpretation: The mechanism for the given information of the reaction is to be explained.
Concept introduction: Steps that correspond to a correct reaction mechanism are shown below.
- The atoms that contain double bond or those containing cations act as electrophiles.
- The atoms with lone pair act as nucleophiles.
- Identify the electrophile site in the given compound.
- Draw the arrow starting from the correct site and ending at the correct site.
(b)
Interpretation Introduction
To determine: The mechanism for the base catalyzed formation of the trimer.
Interpretation: The mechanism for the base catalyzed formation of the trimer is to be stated.
Concept introduction: Steps for correct mechanism are shown below.
- The atoms that contain double bond or those containing cations act as electrophiles.
- The atoms with lone pair act as nucleophiles.
- Identify the electrophiles site in the given compound.
- Draw the arrow starting from the correct site and ending at the correct site.
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Phineas and Ferbs, two brothers who enjoy vacations, doing fun things every summer. This summer the brothers and their friends carry out an organic synthesis with an unknown compound (L1) that contains 52% Carbon, 6% Hydrogen and 42% bromine, this compound (L1) is treated with magnesium in ether to obtain L2 , which reacts violently with D2O for 1-methyl cyclohexene with a deuterium atom in the methyl group (L3). The L2 reaction is treated with acetone followed by hydrolysis to give L4. Heating L4 with concentrated sulfuric acid gives L5, which decolors the bromine, obtaining L6. L5 undergoes hydrogenation with excess hydrogen and platinum as a catalyst giving rise to isobutyl cyclohexane. Determine the structures of compounds L1 through L6.
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b.)What was the product of the second step (reaction involving NaOH)? If something else formed as the product of the first reaction, use that alternative structure as the reactant for this second reaction.
c.)How would you change the reaction conditions (either step 1 or step 2) to ensure you obtained the planned final product as the major product.
Chapter 14 Solutions
Organic Chemistry (9th Edition)
Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2PCh. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5PCh. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8PCh. 14.5 - Prob. 14.9PCh. 14.6 - Prob. 14.10P
Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
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