(a)
Interpretation:
The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.
Concept Introduction:
Hemiacetal is a molecule formed by the addition of an alcohol to an
Answer to Problem 17.71P
Explanation of Solution
Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.
Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:
(b)
Interpretation:
The number of possible stereoisomers of 5-hydroxyhexanal should be determined.
Concept Introduction:
Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of
Answer to Problem 17.71P
5-hydroxyhexanal has 2 stereoisomers.
Explanation of Solution
For a molecule with n stereoisomers, a maximum of
In 5-hydroxyhexanal, there is one stereocenter.
Therefore, number of stereoisomers can be calculated as follows:
Thus, number of stereoisomers will be 2.
(c)
Interpretation:
The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.
Concept Introduction:
Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of
Answer to Problem 17.71P
Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.
Explanation of Solution
For a molecule with n stereoisomers, a maximum of
In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.
Therefore, number of stereoisomers can be calculated as follows:
Thus, number of stereoisomers are 4.
Want to see more full solutions like this?
Chapter 17 Solutions
Introduction to General, Organic and Biochemistry
- 18-28 Arrange these compounds in order of increasing acidity: benzoic acid, benzyl alcohol, phenol.arrow_forwardThe analgesic Tylenol is often taken by people who are allergic to aspirin. Tylenol contains acetaminophen (structure shown) as the active ingredient. Is the structure of acetaminophen similar to the structure of aspirin? In what way? Would acetaminophen give a positive phenol test? What products would be obtained if acetaminophen were hydrolyzed in acidic aqueous solution?arrow_forwardDraw the molecular structure of p-nitrophenol in an acidic solution and in an alkaline solution.arrow_forward
- Why is the water solubility of a carboxylate salt greater than that of its parent carboxylic acid? A) A carboxylate salt is an ionic compound which is soluble in water. B) A carboxylate salt is less polar than its parent carboxylic acid. C) A carboxylate salt has a lower boiling point than its parent carboxylic acid. D) A carboxylate salt is more readily reduced to an aldehyde than its parent carboxylic acid.arrow_forwardExplain why benzocaine precipitates during the neutralization.arrow_forwardwhy ethyl acetate is immiscible with water?arrow_forward
- Phenylethanol can be oxidised to phenylethanal or phenylethanoic acid, depending on the reagents used (both the alcohol and the aldehyde are of interest for their antimicrobial properties, while the acid is used to treat type II hyperammonemia): A (a) (b) (c) CoH,CH,CHO phenylethanal B C6H5CH₂CH₂OHC₂H₂CH₂CO₂H phenylethanol Suggest reagents (shown as A and B in the scheme above) that could be used to carry out the oxidation of the alcohol to the aldehyde and the acid, respectively. C6H5CH₂- Suggest two other syntheses of phenylethanoic acid, in each case indicating the starting materials and other reagents required, but not giving details of mechanism. One of your proposed syntheses must start with a compound which only contains seven carbon atoms (the acid product contains eight carbon atoms). phenylethanoic acid Phenylethanal can be converted to a hydrate in the presence of aqueous acid, though the position of equilibrium is very far to the left: H H+/H₂O OH C6H5CH₂-C-H OH Explain why…arrow_forwardWhen reacting an acid halide with amines, it is necessary to use at least two moles of the amine because: A) Acid halides are so unreactive that two moles of the attacking nucleophile are needed B) Using one mole of the amine leads to a neutralization reaction between the two reactants C) Excess amine is needed to react with the hydrohalic acid produced D) The second mole of amine is needed for deprotonation.arrow_forwardChemistry Draw a complete arrow pushing mechanism for the following reaction. NaOH ? Aarrow_forward
- In the 1880's, Acetanilide, sold under the name Antifebrin, was widely used as a pain reliever and fever reducer. However, it had many adverse side effects, including cyanosis as a result of methemoglobinemia. The toxic side effects were the result of a small portion of acetanilide being hydrolyzed to aniline. Acetanilide was discontinued and replaced with phenacetin. Later studies show that both acetanilide and phenacetin are metabolized to acetaminophen. This metabolite, which we know as Tylenol, is responsible for the analgesic and antipyretic properties. Part 1: Show a detailed arrow pushing mechanism of the acid catalyzed hydrolysis of acetanilide to aniline Part 2: Propose a synthesis of Acetaminophen from phenol NH NH NH Phenacetin inophen Acetanilide Attach File Browse Local Files Browse Content Collectionarrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) a) Given 7.70 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100% yield? b) A chemist ran the reaction and obtained 5.25 g of ethyl butyrate. What was the percent yield? c) The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.70 g of butanoic acid and excess ethanol?arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning