Concept explainers
(a)
To determine: The type of reaction that fumarase catalyze.
Interpretation: The given question stated that many enzymes catalyze reactions are similar to reaction that might be used for
Concept introduction: The general steps followed by hydration reaction are stated below:
- First protonation of the
alkene take place to generate the carbocation. - Formation of protonated alcohol.
- Deprotonation.
(b)
To determine: If fumaric acid and malic acid is chiral and the product, malic acid is optically active or not.
Interpretation: The given question stated that many enzymes catalyze reactions are similar to reaction that might be used for organic synthesis. Enzymes are tend to be stereospecific in their reactions and asymmetric induction is also common. The given reaction is the part of the tricarboxylic acid cycle of cell respiration and resembles a reaction that might be used in the laboratory but enzyme-catalyzed reaction gives only the (S) enantiomer of the product, malic acid. Fumaric acid and malic acid is chiral and the product, malic acid is optically active or not is to be predicted.
Concept introduction: Chiral carbon is an “asymmetric carbon that is attached to four different types of atoms.” Due to asymmetric carbon, they do not posses plane of symmetry and are optically active compounds.
(c)
To determine: If the given reaction is precede in the laboratory using sulphuric acid as the catalyst, the product will be optically active.
Interpretation: The given question stated that many enzymes catalyze reactions are similar to reaction that might be used for organic synthesis. Enzymes are tend to be stereospecific in their reactions and asymmetric induction is also common. The given reaction is the part of the tricarboxylic acid cycle of cell respiration and resembles a reaction that might be used in the laboratory but enzyme-catalyzed reaction gives only the (S) enantiomer of the product, malic acid. If the given reaction is precede in the laboratory using sulphuric acid as the catalyst, the product will be optically active or not is to be predicted.
Concept introduction: Optically active compounds are the compounds, which posse’s asymmetric carbon or chiral carbon. They can rotate plane polarised light in anticlockwise direction.
(d)
To determine: The fumarase enzyme is to be a chiral molecule or not.
Interpretation: The given question stated that many enzymes catalyze reactions are similar to reaction that might be used for organic synthesis. Enzymes are tend to be stereospecific in their reactions and asymmetric induction is also common. The given reaction is the part of the tricarboxylic acid cycle of cell respiration and resembles a reaction that might be used in the laboratory but enzyme-catalyzed reaction gives only the (S) enantiomer of the product, malic acid. The fumarase enzyme is to be a chiral molecule or not is to be predicted.
Concept introduction: Chiral carbon is an “asymmetric carbon that is attached to four different types of atoms.” Due to asymmetric carbon, they do not posses plane of symmetry and are optically active compounds.
(e)
To determine: The enzyme-catalyzed reaction is a syn or anti addition.
Interpretation: The given question stated that many enzymes catalyze reactions are similar to reaction that might be used for organic synthesis. Enzymes tend to be stereospecific in their reactions and asymmetric induction is also common. The given reaction is the part of the tricarboxylic acid cycle of cell respiration and resembles a reaction that might be used in the laboratory but enzyme-catalyzed reaction gives only the (S) enantiomer of the product, malic acid. The given reaction takes place in
Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on
(f)
To determine: The fisher projection to show the stereoisomer of deuterated malic acid
Interpretation: The given question stated that many enzymes catalyze reactions are similar to reaction that might be used for organic synthesis. Enzymes tend to be stereospecific in their reactions and asymmetric induction is also common. The given reaction is the part of the tricarboxylic acid cycle of cell respiration and resembles a reaction that might be used in the laboratory but enzyme-catalyzed reaction gives only the (S) enantiomer of the product, malic acid. The conversion of fumaric acid to deuterated malic acid by using hydroboration with
Concept introduction: An asymmetric carbon atom is represented as a cross in Fisher projection. The carbon chain is kept along the vertical line. The groups attached asymmetric carbon atoms are arranged according to their configuration in Fisher projection. The enantiomers of a chiral compound can be named with the help of right hand and left hand configuration.
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ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
- 1. Ketones react with sodium acetylide (the sodium salt of acetylene, Na“:C=CH) to give alcohols. For example: OH 2 H;0 a. Is the product chiral? b. Draw both major and minor reaction products, assuming that the reaction takes place preferentially from the Re face of the carbonyl group. Is the product mixture optically active? Explain.arrow_forward4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.arrow_forwardThe chiral catalyst (R)-BINAP-Ru is used to hydrogenate alkenes to give alkanes . The products are produced with high enantiomeric excess. An example is the formation of (S)-naproxen, a pain reliever. Q.How can one enantiomer of naproxen be formed in such high yield?arrow_forward
- 4. Draw all the stereoisomers of (a) 3-chloro-2-pentanol and (b) 2-bromo-3-hydroxybutane. Give the stereochemistry relationships of stereoisomers (indicate which isomers are enantiomers / diastereomers).arrow_forwardWhich of the following pairs are stereoisomers? a. Propanoic acid and lactic acid b. S-(+)-limonene and R-(-)-limonene c. Ethyl alcohol and dimethyl ether d. None of the choices e. 2-methylpropane and butanearrow_forwardReaction of (CH3)3CH with Cl2 forms two products: (CH3)2CHCH2Cl (63%) and (CH3)3CCl (37%). Why is the major product formed by cleavage of the stronger 1° C–H bond?arrow_forward
- Formaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative. When pure, formaldehyde trimerizes to give trioxane, C3H6O3, which, surprisingly enough, has no carbonyl groups. Only one monobromo derivative (C3H5BrO3) of trioxane is possible. Propose a structure for trioxane.arrow_forwardFill in the boxes with the correct organic structure. You must show relative stereochemistry where necessary. You only need to draw one enantiomer if the product is a racemic mixture. 1. OsO4 2. NaHSO3 MCPBA HglO6 1. NaOH 2. HCIarrow_forward4. A hydrocarbon with IHD of 2 showed a persisting yellow color in the bromine test. What is the likely identity of the compound? a bicyclic compound an alkene a benzene ring an alkyne a straight chain hydrocarbonarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning