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) CoH5CH, CHO phenylethanal CH₂CH₂CH₂OH 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-C B 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). - CoH,CH,CO,H 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 the hydrate is unstable and how the introduction of halogen substituents on the CH2 group could help to make it much more stable.

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) CoH5CH, CHO phenylethanal CH₂CH₂CH₂OH 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-C B 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). - CoH,CH,CO,H 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 the hydrate is unstable and how the introduction of halogen substituents on the CH2 group could help to make it much more stable.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter3: Organic Compounds: Alkanes And Their Stereochemistry

Section3.SE: Something Extra

Problem 38AP: Give IUPAC names for the following compounds:

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