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Concept explainers
(a)
Interpretation:
The reaction mechanism for the conversion of benzoic acid into phenylacetic acid,
Concept introduction:
Carboxylic acids can be reduced by using strong reducing agents like
(b)
Interpretation:
The reaction mechanism for the conversion of benzoic acid into
Concept introduction:
Carboxylic acids can be reduced by using strong reducing agents like
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Chapter 20 Solutions
EBK ORGANIC CHEMISTRY
- 18-28 Arrange these compounds in order of increasing acidity: benzoic acid, benzyl alcohol, phenol.arrow_forwardShow how you would synthesize each compound, starting with an ester containing nomore than eight carbon atoms. Any other necessary reagents may be used.(a) Ph3C¬OH (b) (PhCH2)2CHOHarrow_forward17-48 How would you prepare the following compounds from More than one step may be required. 1-phenylethanol? (a) Acetophenone (PhCOCH3) (b) Benzyl alcohol (c) m-Bromobenzoic acid (d) 2-Phenyl-2-propanol 17-49 How would you prepare the following substances from cyclopentanol? More than one step may be required. (a) Cyclopentanone (b) Cyclopentene (c) 1-Methylcyclopentanol (d) trans-2-Methylcyclopentanol 17-50 What products would you expect to obtain from reaction of 1-methyl- cyclohexanol with the following reagents? (a) HBr (b) NaH (c) H₂SO4 (d) Na₂Cr₂O7arrow_forward
- write the mechanism for a decarboxylation and state the structural features necessary for a decarboxylation.arrow_forwardWhich, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate (c) Ethyl 2-rnethylbutanoate (d) Ethyl 2,2-dimethylpropanoate (b) Ethyl 3-methylbutanoatearrow_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
- Ethyl 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_forwardCarboxylic Acid Derivatives Resolve by synthesis, step by step.arrow_forward(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Yarrow_forward
- (a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from?arrow_forward14. What is the IUPAC name for the following compound? NH- (a) propyl propanamide (b) propyl propanoate (c) N-propylptopanamine. (d) N, N-propylpropanamide (e) N-propxlpropanamidearrow_forwardComparing Hydration Products Using Two Different Methods Draw the product formed when CH3CH2C=CH is treated with each of the following sets of reagents: (a) H2O, H2SO4, HgSO4; and (b) R2BH, followed by H2O2, HO−.arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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