Concept explainers
(a)
Interpretation:
The mechanism is to be given for the conversion of 2,4,6-trimethylphenol to compound A.
Concept introduction:
SN2 reaction:
The alcohols is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.
(b)
Interpretation:
The stereo selectivity and region selectivity of the conversion of compound C to compound F is to be given.
Concept introduction:
Hydrobromination:
A hydrobromination reaction is one of the electrophilic additions to
(c)
Interpretation:
The product formation of the reaction is single enantiomer or racemic mixture has to be explained.
Concept introduction:
Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.
Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.
Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.
Achiral:
A molecule is superimposable on its mirror image is called achiral molecule.
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Chapter 21 Solutions
Organic Chemistry
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- γ-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-Butyrolactone shows an absorption in its IR spectrum at 1770 cm−1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of γ-butyrolactone?arrow_forwardCompound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forwardTwo isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?arrow_forward
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning