Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 15.5, Problem 11P
Is the following statement true or false?
If the newly added group in the tetrahedral intermediate is a stronger base than the group attached to the acyl group in the reactant, then formation of the tetrahedral intermediate is the rate-limiting step of a nucleophilic acyl substitution reaction.
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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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- Bulky, nonnucleophilic bases favor elimination over substitution. Define this ?arrow_forwardWhich of the following is the rule which states that the more substituted product is the major product in an elimination reaction? O 1) Boyle's Law O 2) Markovnikov's Rule 3) Zaitsev's Rule O 4) LeChatlier's Principlearrow_forwardDraw the enol intermediate formed for this reactionarrow_forward
- Acetal product formation requires an acid catalyst in the second step, but NOT in the first step. True or False?arrow_forwardAn S 2 reaction takes place where a nucleophile displaces a leaving group at a stereocentre. If the stereocentre in the reactant is (R), which of the following is true? A) The stereocentre in the product will become (S) B) The stereocentre in the product will stay (R) C) Not enough information is given to answer the question 14arrow_forwardWrite TRUE if the underlined word/phrase makes the statement correct. Otherwise, write the correct WORD/PHRASE that will make the statement true. 1. Aldehydes and ketones generally react in a mechanism known as nucleophilic substitution reaction at the carboxylic oxygen. 2. 1-cyclopentylethan-1-one will test positive in baeyer's test and will test positive in tollen's test. 3. Gulose and idose produce the same osazones. 4. Seliwanoff's test can be used to differentiate sorbose and talose 5. Ribose is a C2 epimer of arabinose and a C4 epimer of xylose. 6. In the test for benzoic acid, boiling-off excess FeCl3 prevents the formation of Fe(OH)3 precipitate. 7. The vapor produced from the base-promoted hydrolysis of propanamide turned the blue litmus paper to red. 8. Anhydrous Na₂SO4 was added in the obtained organic layer to remove excess water. 9. In the synthesis of esters, using acyl chlorides as starting materials instead of carboxylic acids could decrease the product yield. 10. The…arrow_forward
- Why are the carboxylic acid groups added in a syn orientation during hydrolysis for the following reaction?arrow_forwardWrite the ambident nucleophiles? Give an example.arrow_forwardOnly one of these statements about nucleophilic aromatic substitution is true. O as the number of ortho and para electron withdrawing groups increases, the reaction rate decreases O the reaction proceeds by an addition-elimination mechanism the reaction involves a carbocation intermediate with delocalization of electrons all are falsearrow_forward
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