Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 15.8, Problem 27P
Write the mechanism for the acid-catalyzed reaction of tert-butyl acetate with methanol.
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1) NaNH2 (excess)
1) NaNH2
CI CI
2) H₂O
2) Mel
1) 03
2) (CH3)2S
Na
NH3 (liquid)
1
CI
1) n-BuLi
2)
1) 03
HH
T&Cl
2) H₂O
2
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Chapter 15 Solutions
Organic Chemistry (8th Edition)
Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3PCh. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6PCh. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...
Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13PCh. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17PCh. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21PCh. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23PCh. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25PCh. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28PCh. 15.9 - Prob. 29PCh. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32PCh. 15.11 - Prob. 33PCh. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35PCh. 15.12 - Prob. 36PCh. 15.13 - Prob. 37PCh. 15.14 - Prob. 38PCh. 15.14 - Prob. 39PCh. 15.15 - Prob. 40PCh. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43PCh. 15.16 - Prob. 44PCh. 15.16 - Prob. 45PCh. 15.17 - Prob. 46PCh. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48PCh. 15 - Name the following:Ch. 15 - Prob. 50PCh. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68PCh. 15 - Prob. 69PCh. 15 - Prob. 70PCh. 15 - Prob. 71PCh. 15 - Prob. 72PCh. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75PCh. 15 - Prob. 76PCh. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78PCh. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81PCh. 15 - Prob. 82PCh. 15 - Prob. 83PCh. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86PCh. 15 - Prob. 87PCh. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89PCh. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P
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- For the following compound: HO -H Draw a mechanism for the tautomerization process under BASIC conditions: Mechanism A: H-O: H-OH H-O HH H-OO Mechanism B: H-Q Mechanism C: Θ OH H-O: Mechanism D: H-O H- H-OO C H-OO H- H- H-OO HH OH -H - HON H :OH H-Harrow_forwardidentify the product (or multiple products) for each of the following reactions: CI 1) NaNH2 (excess) ठ Cl 2) H₂O Hz H₂SO₂, H₂O HgSO Lindlar's catalyst 1) n-BuLi 2) 1)9-BBN 2) H₂O, NaOH ? Br H A B C afó gó H OA B O c OD E OF D E F H H Na, NHarrow_forwardIdentify the product (or multiple products) for each of the following reactions: ? or CI CI 1) NaNHz (excess) 2) H₂O OA OB O C OD OE OF H₂SO₂, H₂O Hq50. 1) n-BuLi 2) Br 1) 9-BBN 2) H₂O₂, NaOH A B H H متته D E H H H H C H H F H H H₂ Lindlar's catalyst Na NHarrow_forward
- Identify the product (or multiple products) for each of the following reactions: O A OB Oc OD OE OF CI CI 1) NaNH2 (excess) 2) H₂O H₂ H₂SO2, H₂O HgSO Lindlar's catalyst 1) n-BuLi 2) Br 1)9-BBN 2) H₂O₂, NaOH ? Na, NH3 C H A H H مننه مننه منن مننه H F H H E مند H D H Harrow_forwardFor the following compound: HO H Draw a mechanism for the tautomerization process under BASIC conditions: Mechanism A: + H-O: H-OH₂ H Mechanism B: H-Ö: HO-H H-OO -H H HH H H HH H-O: H-OO H-OO -H H e -H : OH Θ Mechanism C: Θ A : OH H-O: H H H-O-H 0. Mechanism D: e.. : OH :0 H H-O-H H-O: H-OO :O H -H H H сём H 0 :0 + H Θ H H H-arrow_forwardFor the following compound: H OH Draw a mechanism for the tautomerization process under ACIDIC conditions: Mechanism A: Θ :OH O O-H HO 0: Mechanism B: :O-H e.. Θ :OH Mechanism C: H HO-H :0: Θ 0: H H e.. : OH 0: "Θ HH O. :OH :OH O-H O-H Mechanism D: :OH H-OH₂ :OH HO-H 0: © O-H H HH 0: HHarrow_forward
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