aldehyde and ketones with featured...
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![Page 1: Aldehyde and Ketones with Featured reactionsceng.tu.edu.iq/ched/images/lectures/chem-lec/st1/c1... · 2013-09-25 · 1.What is the general structure for an aldehyde? A ketone? * 2.How](https://reader031.vdocuments.site/reader031/viewer/2022040901/5e72434de452a0290a674d87/html5/thumbnails/1.jpg)
*
Aldehyde and Ketones with
*Featured reactions
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*
*1.What is the general structure for an aldehyde? A ketone?
*2.How are the common names of aldehydes and ketones
determined? How are aldehydes and ketones named using
IUPAC nomenclature?
*3.Why are the boiling points of aldehydes and ketones higher
than those of ethers and alkanes of similar molar masses, but
lower than those of comparable alcohols?
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*
*4.How do the solubilities of aldehydes and ketones of four
carbons or less compare to the solubilities of comparable
alkanes and alcohols in water?
*5.How are aldehydes and ketones prepared?
*6.What typical reactions take place with aldehydes and
ketones?
*7.What are some common aldehydes and ketones and their
uses?
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*
*Carbon atom joined to oxygen by a double
bond
*Ketones
*Aldehydes
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*
Comes from alcohol dehydrogenation
Obtained by removing of a hydrogen
from an alcohol
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**Both common and IUPAC names frequently used
*Common names from acids from which aldehydes can be
converted
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*
*IUPAC
*Longest chain with aldehyde
*Drop “e” and add “-al”
*Aldehyde takes precedence over all other
groups so far
*Examples
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*
*Naming:
*Drop “e”, add “-one”
*Many common names
*Simplest is 3 carbons
*C. name: acetone
*IUPAC: propanone
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*
*Carbonyl carbon gets lowest number
*See examples…
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** Formaldehyde
* Manufactured from methanol
* Used in many polymers
* Acetaldehyde
* Prepared from ethyl alcohol
* Formed in the detoxification of alcohol in the liver
* Acetone
* Formed in the human body as a by-product of lipid metabolism
* Excreted in the urine
* Hormones
* Steroid hormones
* Progesterone/Testosterone
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*
*Carbon-oxygen double bond is very polar
*Affects boiling points
*More than ethers (C-O bonds)
*Less than alcohols (C-OH bonds)
*Odors
*Low aldehydes very pungent
*High aldehydes pleasant odors (perfumes)
*Solubility
*Similar to alcohols and ethers
*Soluble up to about 4 carbons
* Insoluble after that
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**Oxidation
*Leads to carboxylic acid unless care is taken
*1° alcohols
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*
*Oxidation of a 2° alcohol
*Utilizes chromium compounds and sulfuric acid
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*
*Both under-go combustion reactions
*Oxidation
*Aldehydes can be oxidized, ketones can’t
*See Pg 403
*Tollen’s reagent
*Benedict’s reagent
*Fehling’s reagent
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*
*Reduction
*Variety of agents can reduce aldehydes and ketones to alcohols
*NaBH4 and H2 commonly used
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*
*Hydration
*Formaldehyde dissolves readily in water
*Acetaldehyde somewhat also
*Form hydrates
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*
*Addition of Alcohols to Carbonyl Groups
*Hemiacetal
*Aldehyde + alcohol
*Hemiketal
*Ketone + alcohol
*Not very stable
*Differs from
*1 mol to 2 mol
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*
*Hemiacetals + HCl = acetal
*Hemiketal + HCl = ketal
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*
*oxidation
* reduction
* nucleophilic addition
*Aldehydes are easily oxidized, ketones are not.
*Aldehydes are more reactive in nucleophilic
additions than ketones.
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*
*Reactions of aldehydes and ketones:
* oxidation
* reduction
* nucleophilic addition
*Aldehydes are easily oxidized, ketones are not.
*Aldehydes are more reactive in nucleophilic additions than ketones.
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reduction reduction
oxidation
nucleophilic
addition
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*
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*
1)
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*
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*Aldehydes & ketones, reactions:
*Oxidation
*Reduction
*Addition of cyanide
*Addition of derivatives of ammonia
*Addition of alcohols
*Cannizzaro reaction
*Addition of Grignard reagents
* (Alpha-halogenation of ketones)
* (Addition of carbanions)
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* 1) Oxidation
* Aldehydes (very easily oxidized!)
* CH3CH2CH2CH=O + KMnO4, etc. CH3CH2CH2COOH
* carboxylic acid
* CH3CH2CH2CH=O + Ag+ CH3CH2CH2COO- + Ag
* Silver mirror
* Tollen’s test for easily oxidized compounds like aldehydes.
* (AgNO3, NH4OH(aq))
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*
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*
test for methyl ketones Yellow ppt
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*
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Then + H+ alcohol
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*
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* melting points of derivatives
* ketones bp semi- 2,4-dinitro- oxime
* carbazone phenylhydrazone
* 2-nonanone 195 119 56
* acetophenone 202 199 240 60
* menthone 209 189 146 59
* 2-methylacetophenone 214 205 159 61
* 1-phenyl-2-propanone 216 200 156 70
* propiophenone 220 174 191 54
* 3-methylacetophenone 220 198 207 55
* isobutyrophenone 222 181 163 94
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*
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*
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Crossed Cannizzaro:
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*
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*Aldehydes & ketones, reactions:
*Oxidation
*Reduction
*Addition of cyanide
*Addition of derivatives of ammonia
*Addition of alcohols
*Cannizzaro reaction
*Addition of Grignard reagents
* (Alpha-halogenation of ketones)
* (Addition of carbanions)
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*Planning a Grignard synthesis of an alcohol:
*The alcohol carbon comes from the carbonyl
compound.
*The new carbon-carbon bond is to the alcohol
carbon.
New carbon-carbon bond
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*Planning a Grignard synthesis of an alcohol:
*The alcohol carbon comes from the carbonyl compound.
*The new carbon-carbon bond is to the alcohol carbon.
New carbon-carbon bond
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* “The Grignard Song” (sung to the tune of “America the Beautiful”)
* Harry Wasserman
* The carbonyl is polarized,
* the carbon end is plus.
* A nucleophile will thus attack
* the carbon nucleus.
* The Grignard yields an alcohol
* of types there are but three.
* It makes a bond that corresponds
* from “C” to shining “C.”
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