0120Ch16 - Chapter 16 Aldehydes and Ketones Ch-16 1 The...

Info iconThis preview shows pages 1–12. Sign up to view the full content.

View Full Document Right Arrow Icon
Chapter 16 Aldehydes and Ketones Ch-16 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
The Carbonyl Group Classes of compounds containing the carbonyl group , C=O. aldehydes and ketones (Chapter 16) 2 Ch-16 C O R" R' C O R H (H) R–CHO R'–CO–R"
Background image of page 2
The Carbonyl Group Classes of compounds containing the carbonyl group , C=O (contd.). Carboxylic acids (Chapter 17) 3 Ch-16 R C O OH RCOOH, RCO 2 H C C O C C O R C O Cl RCOCl (RCO) 2 O R C O C R O O R'COOR" R' C O OR" R 1 C O N R 3 R 2 (H) (H) RCON< Enolate anions (Chapter 19) Acid halides, acid anhydrides, esters, amides (Chapter 18)
Background image of page 3

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

View Full DocumentRight Arrow Icon
The Carbonyl Group The carbonyl group (>C=O) as in aldehydes and ketones consists of one σ (sigma) bond formed by the overlap of sp 2 hybrid orbitals and, in addition, one π (pi) bond formed by the overlap of parallel 2 p orbitals between carbon and oxygen (see Chapter 1.7, Fig. 1.21). 4 Ch-16 O O O O O O O "mix" 2p 2p E 2 electrons π π * vacant, no electron
Background image of page 4
The Carbonyl Group 5 Ch-16 Methanal (Formaldehyde): π bonding MO π antibonding MO Energy
Background image of page 5

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

View Full DocumentRight Arrow Icon
Structure The functional group of an aldehyde is a carbonyl group bonded to an H atom and a C atom: –CH=O (or –CHO). In methanal ( formaldehyde ) the carbonyl group is bonded to two H atoms: H 2 C=O. The functional group of a ketone is a carbonyl group bonded to two carbon atoms. 6 Ch-16
Background image of page 6
Nomenclature: Aldehydes The parent chain is the longest chain that contains the carbonyl group. For an aldehyde , change the alkan e suffix from -e to -al . For an unsaturated aldehyde , change the alk an e infix from - an- to -en- ; the location of the suffix determines the numbering pattern. 7 Ch-16 IUPAC names:
Background image of page 7

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

View Full DocumentRight Arrow Icon
Nomenclature: Aldehydes For a cyclic molecule , in which –CH=O (–CHO) is bonded to the ring, add the suffix -carbaldehyde . 8 Ch-16 The IUPAC naming retains some common names: formaldehyde (H 2 CO), acetaldehyde (CH 3 CHO), benzaldehyde (PhCHO), and cinnamaldehyde. IUPAC names (contd.):
Background image of page 8
Nomenclature: Ketones 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 IUPAC retains the common names acetone , acetophenone , and benzophenone . 9 Ch-16 IUPAC names:
Background image of page 9

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

View Full DocumentRight Arrow Icon
Order of Precedence For compounds that contain more than one functional group indicated by a suffix. 10 Ch-16 Functional Group Suffix if Higher Priority Prefix if Lower Priority Example (when the functional group has lower priority) Carboxyl -oic acid O CO 2 H 2-ethyl-5- oxo pentan oic acid Aldehyde -al oxo- Ketone -one oxo- O O 4- oxo hexan al Alcohol -ol hydroxy- 4- hydroxy hexan al O OH Amine -amine amino- 3- amino propan-1- ol H 2 N OH Sulfhydryl -thiol mercapto- 3- mercapto propan-1- ol HS OH
Background image of page 10
For an aldehyde , the common name is derived from the common name of the corresponding carboxylic acid. 11
Background image of page 11

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

View Full DocumentRight Arrow Icon
Image of page 12
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 04/17/2011 for the course ENY 3005 taught by Professor Staff during the Fall '08 term at University of Florida.

Page1 / 91

0120Ch16 - Chapter 16 Aldehydes and Ketones Ch-16 1 The...

This preview shows document pages 1 - 12. Sign up to view the full document.

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