Interpretation:
The structure of the product on the basis of mass spectra, IR and NMR data is to be determined.
Concept introduction:
Hydrogenolysis reaction of benzyl alcohols results in the cleavage of the benzyl and oxygen bond. It may also involve group migration, which is usually carried out by the phenyl ring.
Infrared absorption bands indicate the
NMR data indicates the number and types of protons or carbons present in a compound based on the number of signals obtained in
The mass spectra of a compound indicate the molecular ion peak, which give the molecular mass of the compound.
Want to see the full answer?
Check out a sample textbook solutionChapter 16 Solutions
Organic Chemistry
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forwardFollowing is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forwardIn the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents. Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. (a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid? (b) How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?arrow_forward
- Lipoic acid is required by many microorganisms for proper growth. As a disulfide, it functions in the living system by catalyzing certain oxidation reactions and is reduced in the process. Write the structure of the reduction product.arrow_forwardWhat products would result from the following processes? Write an equation for each reaction. a. 2-Methyl-2-butanol is subjected to controlled oxidation. b. 1-Propanol is heated to 140C in the presence of sulfuric acid. c. 3-Pentanol is subjected to controlled oxidation. d. 3-Pentanol is heated to 180C in the presence of sulfuric acid. e. 1-Hexanol is subjected to an excess of oxidizing agent.arrow_forwardAccount for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.arrow_forward
- Provide the necessary reagents to accomplish the desired organic reactions. Please number the steps and note that some reactions will require more than one step.arrow_forwardGrignard reagents can react with ester functional groups to form tertiary alcohols. What is the final product of the following reaction?arrow_forwardStarting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. Q.) cis-1,2-Cyclohexanediolarrow_forward
- Isoamyl acetate is the common name of the substance most responsible for the characteristic odor of bananas. Write a structural formula for isoamyl acetate, given the information that it is an ester in which the carbonyl group bears a methyl substituent and there is a 3-methylbutyl group attached to one of the oxygens.arrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. ROH, H+ OH OR Aldehyde/ketone Alcohol ROH, H+ Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds: OH OH OR OR • Use the wedge/hash bond tools to indicate stereochemistry where it exists. + H₂Oarrow_forwardProvide the major organic product of the following reaction. H3O', heatarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole