Organic Chemistry 6: Aldehydes and Ketones: Electrophilicity and Oxidation-Reduction

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39 Terms

1
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An aldehyde is a terminal functional group containing a/an [...] bonded to at least one [...]

carbonyl bonded to at least one hydrogen

<p>carbonyl bonded to at least one hydrogen </p>
2
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[...] have the suffix -al

aldehydes

  • aldehydes take their name from their parent alkane chains

  • - the -e is removed from the end and is replaced with -al

<p>aldehydes </p><ul><li><p>aldehydes take their name from their parent alkane chains </p></li><li><p>- the -e is removed from the end and is replaced with -al </p></li></ul><p></p>
3
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[...] use the suffix -one and the prefixes oxo- or keto-

ketones

  • ketones take their name from their parent alkane chains

  • the ending -e is removed and replaced with -one

<p>ketones </p><ul><li><p>ketones take their name from their parent alkane chains </p></li><li><p>the ending -e is removed and replaced with -one </p></li></ul><p></p>
4
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The aldehyde functional group is given the number [...] numbering location

1

<p>1 </p>
5
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A ketone is an internal functional group containing a/an [...] bonded to two [...]

carbonyl bonded to two alkyl chains

<p>carbonyl bonded to two alkyl chains </p>
6
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A [...] is a carbon-oxygen double bond

carbonyl group

<p>carbonyl group </p>
7
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Aldehydes and ketones are synthesized from alcohols through [...]

oxidation

<p>oxidation </p>
8
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A weak oxidizing agent like [...] must be used for synthesizing aldehydes from alcohols, or else the reaction will continue oxidizing and form a carboxylic acid

pyridinium chlorochromate (PCC)

<p>pyridinium chlorochromate (PCC)</p><img src="https://knowt-user-attachments.s3.amazonaws.com/a50bcaac-1183-49da-9f0d-e7d128f7088f.png" data-width="100%" data-align="center"><p></p>
9
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KMnOand H2Cr2O4 are [weak or strong] oxidizing agents

strong

  • they will oxidize an alcohol all the way into a ketone or carboxylic acid

<p>strong </p><ul><li><p>they will oxidize an alcohol all the way into a ketone or carboxylic acid </p></li></ul><p></p>
10
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11
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NaBH4 is a [weak or strong] reducing agent 

weak

  • it will reduce an aldehyde or a ketone into an alcohol, but will not reduce a carboxylic acid or an ester

<p>weak </p><ul><li><p>it will reduce an aldehyde or a ketone into an alcohol, but will not reduce a carboxylic acid or an ester </p></li></ul><p></p>
12
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A strong reducing agent like [...] is needed to reduce a carboxylic acid or an ester into an alcohol

LiAlH4 (LAH)

<p>LiAlH4 (LAH)</p>
13
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Nucleophilic addition reactions involve the attack of a nucleophile on the slightly positive [...] of a carbonyl group

carbon center

<p>carbon center </p>
14
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In a hydration reaction, water adds to a carbonyl and forms a/an [...]

geminal diol

<p>geminal diol </p>
15
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16
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When one equivalent of alcohol reacts with an aldehyde, a/an [...] is formed

hemiacetal

<p>hemiacetal </p>
17
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When one equivalent of alcohol reacts with a ketone, a/an [...] is formed

hemiketal

<p>hemiketal </p>
18
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When two equivalents of alcohol react with an aldehyde, a/an[...]is formed

acetal

<p>acetal </p>
19
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When two equivalents of alcohol react with a ketone, a/an [...] is formed

ketal

<p>ketal </p>
20
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Nitrogen and nitrogen derivatives react with carbonyls to form [...]

imines

<p>imines </p>
21
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Imines can tautomerize to form [...]

enamines

  • tautomerization is a reaction which involves simple proton transfer

<p>enamines </p><ul><li><p>tautomerization is a reaction which involves simple proton transfer </p></li></ul><p></p>
22
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Hydrogen cyanide reacts with carbonyls to form [...]

cyanohydrins

<p>cyanohydrins </p>
23
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<p><span>Identify the </span><strong>α-carbon</strong></p>

Identify the α-carbon

knowt flashcard image
24
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<p><span>Identify the </span><strong>α-carbon</strong></p>

Identify the α-carbon

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25
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<p><span>A/an </span><span style="color: mediumseagreen"><strong>[...]</strong></span><span> is formed when an&nbsp;</span><strong><u>α-hydrogen</u></strong><span>&nbsp;in the molecule of an </span><strong>aldehyde</strong><span> or a </span><strong>ketone</strong><span> is&nbsp;</span><strong><u>removed</u></strong></p>

A/an [...] is formed when an α-hydrogen in the molecule of an aldehyde or a ketone is removed

enolate anion

<p>enolate anion </p>
26
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Aldehydes are usually [more or less] reactive toward nucleophilic substitutions than ketones because of both steric and electronic effects

more

<p>more </p>
27
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<p><span>This is the </span><span style="color: mediumseagreen"><strong>[keto or enol]</strong></span><span> form of acetone</span></p>

This is the [keto or enol] form of acetone

keto

  • keto form has a regular ketone or an aldehyde

  • enol form contains an alcohol

<p>keto </p><ul><li><p>keto form has a regular ketone or an aldehyde</p></li><li><p>enol form contains an alcohol </p></li></ul><p></p>
28
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The term "enol" comes from the fact that it is a/an [...] that is also a/an [...]

alkene

alcohol

<p>alkene </p><p>alcohol </p>
29
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[...] refers to a chemical equilibrium between a keto form and an enol

keto-enol tautomerization

  • the keto and enol form are said to be tautomers of each other

  • they can be interconverted by moving a hydrogen and a double bond

<p>keto-enol tautomerization </p><ul><li><p>the keto and enol form are said to be tautomers of each other </p></li><li><p>they can be interconverted by moving a hydrogen and a double bond </p></li></ul><p></p>
30
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Keto form is much [more or less] common than enol form

more

  • can be attributed to the fact that a C+O double bond is significantly more stable (higher bond energy) then a C=C double bond

<p>more</p><ul><li><p>can be attributed to the fact that a C+O double bond is significantly more stable (higher bond energy) then a C=C double bond </p></li></ul><p></p>
31
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In a Michael addition, a/an [...] attacks a/an [...], creating a bond

enolate attacks a/an α,β-unsaturated carbonyl, creating a bond

 

<p>enolate attacks a/an <span style="color: mediumseagreen"><strong>α,β-unsaturated carbonyl</strong></span><span>,&nbsp;creating a bond</span></p><p>&nbsp;</p>
32
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<p><span>Removal of a proton from the</span><strong>&nbsp;less substituted</strong><span>&nbsp;(and less hindered) α-carbon gives the </span><span style="color: mediumseagreen"><strong>[kinetic or thermodynamic]</strong></span><span> enolate</span></p>

Removal of a proton from the less substituted (and less hindered) α-carbon gives the [kinetic or thermodynamic] enolate

kinetic

  • the kinetic enolate has the less substituted C=C double bond

<p>kinetic </p><ul><li><p>the kinetic enolate has the less substituted C=C double bond </p></li></ul><p></p>
33
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<p><span>Removal of a proton from the </span><strong><u>more substituted</u></strong><span> (and more hindered) α-carbon gives the </span><span style="color: mediumseagreen"><strong>[kinetic or thermodynamic]</strong></span><span> enolate&nbsp;</span></p>

Removal of a proton from the more substituted (and more hindered) α-carbon gives the [kinetic or thermodynamic] enolate 

thermodynamic

  • the thermodynamic enolate has the more substituted C=C double bond

<p>thermodynamic </p><ul><li><p>the thermodynamic enolate has the more substituted C=C double bond </p></li></ul><p></p>
34
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An aldol is a/an [...] plus a/an [...]

aldehyde plus a/an alcohol

<p>aldehyde plus a/an alcohol </p>
35
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Aldol addition is a powerful way to create a [...] bond

carbon-carbon

<p>carbon-carbon </p>
36
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An aldol condensation starts with a/an [...] to create a/an [...]

aldol addition to create a/an aldol

  • then it undergoes a dehydration to give a conjugated enone (α,β-unsaturated carbonyl)

  • very common in the production of pharmaceuticals and refumes

<p>aldol addition to create a/an aldol </p><ul><li><p>then it undergoes a dehydration to give a conjugated enone (α,β-unsaturated carbonyl)</p></li><li><p>very common in the production of pharmaceuticals and refumes </p></li></ul><p></p>
37
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An aldol nucleophile is the [...] formed from the deprotonation of the α-carbon

nucleophile

<p>nucleophile </p>
38
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The aldol electrophile is a/an [...] or [...]

aldehyde or ketone

<p>aldehyde or ketone </p>
39
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A/an [... reaction] is the reverse of an aldol reaction

reverse

  • the bond between the α- and β-carbon is cleaved Catalyzed by heat

<p>reverse</p><ul><li><p>the bond between the α- and β-carbon is <strong><u>cleaved </u></strong>Catalyzed by <strong>heat</strong></p></li></ul><p></p>