Holooly Plus Logo
Holooly Plus Logo

Question 18.34: Reduction of the ketone group of the following keto ester oc......

Reduction of the ketone group of the following keto ester occurs stereospecifically at the re face using NADH in an enzymecatalyzed reaction. Draw the structure of the product and assign its configuration.

لقطة الشاشة 2023-08-15 224300
Step-by-Step
The 'Blue Check Mark' means that this solution was answered by an expert.
Learn more on how do we answer questions.
Report Answer

The R-enantiomer can only be produced if the NADH adds hydride to the re face of the carbonyl group.

Related Answered Questions

Question: 18.7

Many aldehydes and ketones are better known by their common names. Draw the structural formula of each of the following carbonyl compounds. Their common names are given within parentheses. (a) 2,2-dimethylpropanal (pivaldehyde) (b) 2-hydroxy ...

Verified Answer:

Question: 18.39

Deduce the structure of isomeric ketones having the molecular formula C₁₀H₁₂O based on the following proton NMR spectra. ...

Verified Answer:

The 5H multiplet corresponds to the monosubstitute...
Question: 18.40

Deduce the structure of isomeric ketones having the molecular formula C₉H₁₀O₂ based on the following proton NMR spectra. ...

Verified Answer:

The doublet of 2H doublets between 7 and 8 δ corre...
Question: 18.36

Explain why the carbonyl stretching absorption of cyclohexanones are shifted approximately 20 cm^−1 to higher wavenumber when a bromine atom is substituted in the equatorial position at the α carbon atom. ...

Verified Answer:

The bromine atom withdraws electrons from the carb...
Question: 18.38

Based on the following carbon NMR data, deduce the structures of isomeric ketones having the molecular ormula C₅H₁₀O. (a) 18.1 ppm, 27.3 ppm, 41.5 ppm, 211.7 ppm (b) 13.5 ppm, 18.5 ppm, 29.3 ppm, 45.2 ppm, 206.6 ppm (c) 7.3 ppm, 35.3 ppm, 209.3 ppm ...

Verified Answer:

Compounds with the formula C₅H₁₀O must contain a r...
Question: 18.37

Based on the following C-13 NMR data, deduce the structures of isomeric compounds having the molecular formula C₄H₈O. (a) 25.7 ppm, 68.0 ppm (b) 15.5 ppm, 41.0 ppm, 204.9 ppm (c) 7.9 ppm, 29.4 ppm, ...

Verified Answer:

Compounds with the formula C₄H₈O must contain a ri...
Question: 18.31

What is the product of each of the following reactions? ...

Verified Answer:

(a) The Rosenmund reaction reduces acid chlorides ...
Question: 18.32

What is the product of each of the following reactions? ...

Verified Answer:

(a) The Rosenmund reaction reduces acid chlorides ...
Question: 18.33

Reduction of 5-chloro-2-pentanone by NADPH in an enzyme-catalyzed reaction yields (S)-5-chloro-2-pentanol. From which face does the hydrogenation occur? ...

Verified Answer:

The S-enantiomer can only be produced if the NADPH...
Question: 18.35

Explain why the IR absorption of the C=C bond of 1-butene (1642 cm^−1) is at higher wavenumber than the C=C bond absorption of 3-buten-2-one (1613 cm^−1). ...

Verified Answer:

The double bond of 3-buten-2-one is conjugated to ...