Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 15.4, Problem 8P
What is the product of an acyl substitution reaction—a new
- a. a stronger base than the substituent that is attached to the acyl group
- b. a weaker base than the substituent that is attached to the acyl group
- c. similar in basicity to the substituent that is attached to the acyl group
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What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following?
a. a stronger base than the substituent that is attached to the acyl group b. a weaker base than the substituent that is attached to the acyl group c. similar in basicity to the substituent that is attached to the acyl group
What explains why many aldehydes and ketones can undergo self- condensation reactions in basic conditions?
A. The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon a an electrophile
B. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile
C. The oxygen of the carbonyl group can attack the carbon of the carbonyl group
D. Only esters can undergo self-condensation reactions
Reactions of carbonyl compounds with hydride ion donors.
a. Draw reaction of an aldehyde with sodium borohydride forms a primary alcohol.
b. Draw reaction of a ketone with sodium borohydride forms a secondary alcohol.
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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- What is the major difference between the base-catalyzed and acid-catalyzed processes for nucleophilic addition of water to aldehydes and ketones? a. The base-catalyzed reaction takes place rapidly because hydroxide ion is a much better nucleophile than neutral water. b. The rate of reaction in base catalyzed process is slower than acid catalyzed process. c. The acid-catalyzed reaction takes place rapidly because the protonated carbonyl compound is a much better electrophile than the neutral compound. d. Only 1 and 3 are correct.arrow_forwardHelparrow_forward4-methyl-1 -pentene reacts with hydrogen bromide. a. Draw a structure for the carbocation intermediate that leads to the major Markovnikov product in the reaction of hydrogen bromide with 4-methyl-1-pentene. b. Using Markovnikov's rule, draw a structure of the major organic product formed in the reaction of hydrogen bromide with 4-methyl-1-pentene.arrow_forward
- 1. Which carbonyl group of the given compound is most reactive for nucleophilic addition reaction? a. All have equal reactivity b. Carbonyl Group 1 c. Carbonyl Group 2 d. Carbonyl Group 2. An aldehyde commonly exhibits a nucleophilic addition type of reaction. When a nucleophile attacks a carbonyl carbon, what happens to the oxygen atom in the structure? Refer to the structure below. ~ a. Oxygen atom becomes more electronegative. b. Oxygen atom obtains a net negative charge. c. Oxygen atom transforms to an alkoxide group. d. Oxygen atom acts as the new electrophile. 3. Assign the trivial name of the structure below. a. Diphenylketone b. Benzyl phenylketone c. Diphenyl aldehyde d. Benzyl phenyl aldehydearrow_forward. Which of the following can be both formed from bromoethane and converted directly into ethanal? CH3CH2Br → X → CH3CHO a. CH3CH2OH b. CH3OCH3 c. CH3COOH d. H2C=CHBrarrow_forwardWhich of the following reactions will result in the formation of an acyl halide? Select one: a. The reaction of a carboxylic acid with phosphorus trichloride. b. The treatment of an alcohol with ethyl bromide. c. The reaction of an ester with hydrochloric acid. d. The addition of an alkene to dilute hydrochloric acid.arrow_forward
- Consider the structure of pent-2-ene, if it undergoes ozonolysis, which of the following final product is formed? a.Ethanal and Propanal b.Ethanal and Propanone c.CO2 and Propanal d.Ethanal and CO2arrow_forwardWhich alkyl halides form the carboxylic acids listed here after reaction with sodium cyanide followed by heating the product in an acidic aqueous solution? a. butyric acid b. isovaleric acid c. cyclohexanecarboxylic acidarrow_forwardCyclopentanone is treated with chlorine (Cl2) in the presence of acid (H*). What product is formed? A. Chlorocyclopentane B. 1-chloro-1-hydroxycyclopentane C. 2-chlorocyclopentanone D. 3-chlorocyclopentanonearrow_forward
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