Chapter 17 reduction reactions + 1 oxidation reaction

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Last updated 5:26 PM on 4/11/26
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8 Terms

1
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Reagents needed for Reduction of aldehyde and ketone to 1° and 2° alcohols (HINT: THER ARE 3 DIFFERENT SETS, need to know when to use which)

NaBH4, CH3OH

OR
[1] LiAlH4 [2]H2O

OR

H2, Pd-C

<p>NaBH4, CH3OH</p><p>OR<br>[1] LiAlH4 [2]H2O </p><p>OR</p><p>H2, Pd-C</p>
2
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Reagents for Reduction of a,b-unsaturated aldehydes and ketones (diff reagent in diff amount for reducing different parts (C=O only, C=C only, or reduction of both pi bonds)

NaBH4, CH3OH for reduction of C=O only

H2 (1 equiv), Pd-C for reduction of C=C only

H2 (excess), Pd-C for reduction of both pi bonds

<p>NaBH4, CH3OH for reduction of C=O only</p><p>H2 (1 equiv), Pd-C for reduction of C=C only</p><p>H2 (excess), Pd-C for reduction of both pi bonds</p>
3
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Reagents for enantioselective ketone reduction

[1] (S) or (R) - CBS reagent

[2] H2O

**ONLY FORMS A SINGLE ENANTIOMER DEPENDING ON R or S

<p>[1] (S) or (R) - CBS reagent </p><p>[2] H2O</p><p>**ONLY FORMS A SINGLE ENANTIOMER DEPENDING ON R or S</p>
4
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Reagents for reduction of acid chlorides (2 diff sets, one for making 1° alcohol, one for making aldehyde)

[1] LiAlH4

[2] H2O for 1° alcohol

OR

[1]LiAlH[OC(CH3)3]3

[2] H2O for aldehyde

<p>[1] LiAlH4 </p><p>[2] H2O for 1° alcohol</p><p>OR</p><p>[1]LiAlH[OC(CH3)3]3</p><p>[2] H2O for aldehyde</p>
5
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Reagents for reduction of esters (one for reducing to 1° alcohol, other for reducing to aldehyde)

[1] LiAlH4

[2] H2O for 1° alcohol

OR

[1] DIBAL-H

[2] H2O for aldehyde

<p>[1] LiAlH4</p><p>[2] H2O for 1° alcohol</p><p>OR</p><p>[1] DIBAL-H</p><p>[2] H2O for aldehyde</p>
6
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Reagents for reduction of carboxylic acids to 1° alcohols

[1] LiAlH4

[2] H2O

<p>[1] LiAlH4</p><p>[2] H2O</p>
7
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reagents for Reduction of amides to amines

[1] LiAlH4

[2] H2O

(for turning amides to …)

<p>[1] LiAlH4</p><p>[2] H2O </p><p>(for turning amides to …)</p>
8
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Oxidation of aldehydes to carboxylic acids

** all Cr6+ reagents except PCC oxidize RCHO to RCOOH

** Tollens reagent (Ag2O = NH4OH) oxidizes RCHO only, and does NOT react with 1° or 2° alcohols

<p>** all Cr6+ reagents except PCC oxidize RCHO to RCOOH</p><p>** Tollens reagent (Ag2O = NH4OH) oxidizes RCHO only, and does NOT react with 1° or 2° alcohols</p><p></p>