EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 15.2, Problem 4P
Which is longer, the carbon-oxygen single bond in a
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Which is longer, the carbon–oxygen single bond in a carboxylic acid or the carbon–oxygen bond in an alcohol? Why?
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Chapter 15 Solutions
EBK ORGANIC CHEMISTRY
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 characteristics of carbon make it ideal for the formation of organic compounds?arrow_forwardname and draw the structural formulas for the 4 carboxylic acids with the molecular formula C5H10O2arrow_forwardAmong ethyl, isopropyl, tertiary butyl and n-butyl, which alcohol will first develop a pleasant odor?arrow_forward
- What are the hybridization and bond angles of the oxygens in benzoic acid?arrow_forwardHow does the structure of an alcohol differ from an ether? Describe how an aldehyde differs in structure from a ketone. Thiols are compounds which resemble alcohols, except that the oxygen atom is replaced by a sulfur atom. Draw the analogous thiol for the four carbon alcohol in Table 1. Describe the structural difference between carboxylic acids and esters. Are ethers polar molecules? Would you expect ethers to have higher or lower boiling points than alkanes (circle one)? Explain. Pentane (an alkane) has a boiling point of 36 °C. Does the data agree with your prediction? explain why this could be the casearrow_forwardDoes methanol behave as an acid or a base when it reacts with methylamine?arrow_forward
- Draw the skeletal structure of these carboxylic acids Salicylic acid, acetic acid, propanoic acid, benzoic acidarrow_forwardMany substitution reactions are initiated by electrostatic attraction between reactants. Show where this attraction arises in the formation of an amide from an amine and an ester.arrow_forwardBoth aldehydes and ketones contain carbonyl groups. In aldehydes, the carbonyl carbon atom is bonded to a hydrogen atom, whereas in ketones, the carbonyl carbon atom is bonded to another carbon atom. Select the true statements about aldehydes and ketones. - Ketones have lower boiling points than alcohols of similar size. - Aldehydes contain a carbon–oxygen double bond. - Butanal has a higher boiling point than 2-butanol. - Aldehydes with more than five carbon atoms are soluble in water, but not organic solvents. - Both aldehydes and ketones can hydrogen bond with water molecules. - Propanal is a gas at room temperature, whereas formaldehyde (methanal) is a liquid at room temperature.arrow_forward
- How does hybridization of the substituted carbon atom change when an alcohol is converted into an aldehyde? An aldehyde to a carboxylic acid?arrow_forward1. What are the distinguishing physical properties of carboxylic acids? Describe eac 2. What determines the major physical properties of carboxylic acids? Why? 3. What does polarity of compound or molecule mean?arrow_forwardExplain why a carboxylic acid is not considered to be both a ketone and alcohol?arrow_forward
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