Ch 16 - Nomenclature Compounds with C=O Group IUPAC names:...

Info iconThis preview shows pages 1–9. Sign up to view the full content.

View Full Document Right Arrow Icon
Nomenclature – Compounds with C=O Group IUPAC names: the parent chain is the longest chain that contains the C=O functional group for an aldehyde, change the suffix from -e to -al for an unsaturated aldehyde, change the infix from -an- to -en- ; the location of the suffix determines the numbering pattern for a cyclic molecule in which -CHO is bonded to the ring, add the suffix - carbaldehyde 1
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Nomenclature: Aldehydes the common names benzaldehyde and cinnamaldehyde, as well formaldehyde and acetaldehyde are IUPAC-accepted names H O 3-Methylbutanal 2-Propenal (Acrolein) (2 E )-3,7-Dimethyl-2,6-octadienal (Geranial) 1 2 3 4 5 6 7 8 H O H O CHO HO CHO Cyclopentane- carbaldehyde trans -4-Hydroxycyclo- hexanecarbaldehyde 1 4  CHO C 6 H 5 CHO trans -3-Phenyl-2-propenal (Cinnamaldehyde) Benzaldehyde 2
Background image of page 2
Nomenclature: Ketones IUPAC names the parent alkane is the longest chain that contains the carbonyl group indicate the ketone by changing the suffix -e to - one number the chain to give C=O the smaller number the common names acetone, acetophenone, and benzophenone are IUPAC-accepted names Propanone (Acetone) Benzophenone 1-Phenyl-1-pentanone Acetophenone O O O O 3
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Common Names for an aldehyde, the common name is derived from the common name of the corresponding carboxylic acid for a ketone, name the two alkyl or aryl groups bonded to the carbonyl carbon and add the word ketone HCH O HCOH O CH 3 CH O CH 3 COH O Formaldehyde Formic acid Acetaldehyde Acetic acid Ethyl isopropyl ketone Diethyl ketone Dicyclohexyl ketone O O O 4
Background image of page 4
Order of Precedence For compounds that contain more than one functional group indicated by a suffix H COOH O COOH O COOH HO OH HS COOH NH 2 Functional  Group Carboxyl -oic acid Aldehyde -al oxo- Ketone -one oxo- Alcohol -ol hydroxy- Amino -amine amino- 3- Oxo propanoic  acid 3- Oxo butanoic a cid 4- Hydroxy butanoic  acid 3- Amino butanoic  acid Example when the  functional group has  a lower priority Sulfhydryl -thiol mercapto 2- M ercapto ethanol Suffix if  higher priority Prefix if lower priority   5
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Physical Properties Oxygen is more electronegative than carbon (3.5 vs 2.5) and, therefore, a C=O group is polar aldehydes and ketones are polar compounds and interact in the pure state by dipole-dipole interaction they have higher boiling points and are more soluble in water than nonpolar compounds of comparable molecular weight 6
Background image of page 6
Common C=O Reactions 1. Addition of a nucleophile to form a tetrahedral carbonyl addition compound 2. Acidic activation of carbonyl to form resonance-stabilized cation which is even more reactive with nucleophiles + C R R O C Nu O   - R R Nu   - Tetrahedral carbonyl addition compound - C O R R H-Nu H-B C O R R H - C O R R H C Nu O-H R R C O R R H H-B + fast + + + + slow + + + 7
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Stereochemistry often the tetrahedral product of addition to a carbonyl is a new chiral center if none of the starting materials is chiral and the
Background image of page 8
Image of page 9
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 03/31/2008 for the course HIST 136 taught by Professor Saiki during the Spring '08 term at UNC.

Page1 / 50

Ch 16 - Nomenclature Compounds with C=O Group IUPAC names:...

This preview shows document pages 1 - 9. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online