[PDF] Unit One Part 2: naming and functional groups

Chapter 6 Amines and Amides - Angelo State University

o recognize the amine and amide functional groups • Learn the Nitrogen-Containing Functional Groups • Nitrogen is in Draw structural formulas for the following molecules:

PHYSICOCHEMICAL PROPERTIES OF ORGANIC MEDICINAL

Cité 25 fois — Most importantly, amides are characterized by a "conjugated system" in which the NBEs of nitrogen can delocalized into the adjacent carbonyl (C=O) group

Unit One Part 2: naming and functional groups

nal group Structure Suffix Prefix General form acid R OH O –oic acid –carboxylic acid

In this handout, all of our functional groups are presented as

- try to draw 3D structures in a zig-zag shape C R C R H H H H C C C NH2 Br Functional groups 1 carboxylic acid 2 amide 3 bromo 4 alkene 5 amine 6 nitrile c

Drug Design: Functional groups / Pharmacological - UiO

ructure Activity Relationships Acetylcholine agonists: Identification of acidic / basic functional groups Amide 6 2 - 3 Ex monofuctional comp methanol - pentanol/hexanol

Structure - Activity Relationships

Cité 3 fois — which functional groups are important for binding and for binding and activity • 1o and 2o amines are converted to 2o and 3o amides respectively • amides cannot 

Functional Groups

nal Groups functional group: an atom, or group of atoms (with specific connectivity), exhibiting

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r percentage of amide functional groups in nylon molecules' structures leads to stronger hydrogen 

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Unit One Part 2: naming and functional groups

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• To write and interpret IUPAC names for small, simple molecules• Identify some common functional groups found in organic molecules

1 viagra™ (trade name) sildenafil (trivial name) pyrazolo[4,3-d] pyrimidin-7(6H)-one N N N N S N N H 3 C H 3 C O O CH 3 H 3 C O O H dr gareth rowlands; g.j.rowlands@massey.ac.nz; science tower a4.12 http://www.massey.ac.nz/~gjrowlan

Systematic (IUPAC) naming

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• Comprises of three main parts• Note: multiple bond index is always incorporated in parent section

2 substituents / minor functional groups number of C

AND multiple bond

index principal functional group

SUFFIXPREFIXPARENT

No. CarbonsRootNo. CarbonsRoot1meth6hex

2eth7hept3prop8oct4but9non5pent10dec

Bond

Multiple-bond

index

C-Can(e)C=Cen(e)C㲇Cyn(e)

Systematic (IUPAC) naming: functional groups

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Functional groupStructureSuffixPrefixGeneral form

acid ROH O -oic acid -carboxylic acid carboxyR-COOHanhydride ROR OO -oic anhydride -carboxylic anhydride

R-C(O)OC(O)-Racyl chloride

RCl O -oyl chloride -carbonyl chloride chlorocarbonylR-COClester ROR O -oate -carboxylate alkoxycarbonylR-COORamide RNH 2 O -amide -carboxamide carbamoylR-CONH 2 nitrile NR -nitrilecyanoR-C㲇N aldehyde RH O -al -carbaldehyde oxoR-CHOketone RR O -oneoxoR-CO-R alcohol ROH -olhydroxyR-OHamine RNH 2 -amineaminoR-NH 2 ether R O R -etheralkoxyR-O-R alkyl bromide (alkyl halide) RBr bromo (halo) R-Br (R-X)

Nomenclature rules

gjr--- H 3 CCH 3 CH 3

4-methylheptane

H 3 C CH 3 OH

2-propyl-1-pentanol

1 2 3 4 5 H 3 COH O butanoic acid H 3 CNH 2 OCH 3

3-methylbutanamide

H 3 CCH 3 O

2-pentanone

pentan-2-one

NOT 4-pentanone

1. Parent - root derived from number of carbon in longest unbranched chain

.containing functional group 4

2. Suffix - basic name derived by adding ending of major functional group (FG)3. Position - position of FG denoted by Arabic numeral placed before whole

....name or just before ending. Numbering achieves lowest number for FG

Nomenclature rules II

gjr--- H 3 CCH 3 H 3 CCH 3 CH 3

2,2,5-trimethylheptane

NOT 3,6,6-trimethylheptane

H 3 CCH 3 CH 3 CH 3 Cl

8-chloro-2,3-dimethylnonane

NOT 2-chloro-7,8-dimethylnonane

5

4. Prefix - substituents are designated by prefix & Arabic number indicating

....position (lowest possible numbering)

5. FG - if more than one FG name & number based on principle FG. List of

....priorities given in course notes. Multiple bonds are added to parent (end), ....all others are prefixes

6. Minor FG - halo-, nitro- (-NO

2 ), nitroso- (-NO) & azo- (-N 2 -) are considered ....substituents & not FG for nomenclature only

7. Order - substituents are written in alphabetical order

HOOH O H 3 CCH 3

5-hydroxy-2,2-dimethylpentanoic acid

CH 3 OH O O H 3 C

2-methyl-4-oxohex-2-enoic acid

Examples: structure to name

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Step 1: rootStep 3: multiple-

bond index H 3 CN H O CH 3 OH H 3 CN H O CH 3 OH hept H 3 CN H O CH 3 OH hept-6-enamide 1 2 3 4 5 6 H 3 CN H O CH 3 OH 1 2 3

3-hydroxyhept-6-enamide

H 3 CN H O CH 3 OH hept amide

Step 2: suffixStep 4: functional

groups (prefix) H 3 CN H O CH 3 OH 1 2 3 4 5

3-hydroxy-5-methylhept-6-enamide

Step 5: substituents

(prefix) H 3 CN H O CH 3 OH

N-ethyl-3-hydroxy-5-methylhept-6-enamide

Step 7: complete

Examples: name to structure

gjr--- • Draw the structure for 4-ethyl-3-hydroxycyclohexanone (please) 7 OO H 3 C O H 3 C OH draw the root

4-ethyl-3-hydroxycyclohexanone

add major functional group

4-ethyl-3-hydroxycyclohexanone

add substituent

4-ethyl-3-hydroxycyclohexanone

add minor functional group

4-ethyl-3-hydroxycyclohexanone

Functional groups: alkanes

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• Saturated hydrocarbons - contain only C & H and no multiple bonds• Non-cyclic alkanes have the formula C

n H 2n+2 8 H C H H H methane CH 4 propane C 3 H 8 pentane C 5 H 12 cyclopentane C 5 H 10

• Alkanes are a little dull - used as solvents or burnt as fuel • Methane is a fuel, a chemical feedstock & a green house gas

propane CH 4

Functional groups: alkanes II

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• Isooctane is used in petrol - branched structure means it burns smoothly• Octane is a long change and burns explosively• Octane number of petrol is based on isooctane = 100 & heptane = 1

Unleaded 91 petrol = 91% isooctane & 9% heptane

• Structural isomers have same formula but different atoms joined differently• Isomers can have very different properties

9 isooctane

2,2,4-trimethylpentane

C 8 H 18

2,2-dimethylpropane

2-methylbutane

pentane

Functional groups: alkenes

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• Ethene - simplest alkene. Very important industrially• Carbon is trigonal planar - flat and triangular!

10 H HH H ethene CH 3 H 3 C H 3 C CH 3 CH 3 H 3 C

α-pinene

trans-2-butene H 3 C CH 3 H 3 C CH 3 cis-2-butene

1-butene

C 4 H 8

2-methylpropene

C 4 H 8 cyclobutane C 4 H 8

2-butene

C 4 H 8 • New form of isomerism - configurational isomers • All atoms bonded in the same manner but different orientation in space

Functional groups: alkynes & cyclic structures

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• Ethyne is an explosive gas• Triple bond makes molecular linear (cylinder)• Examples found in nature (example cleaves DNA)

11 HH ethyne C 2 H 2 O O O O O O O H 3 C OME OH O OH HO CH 3 MeHN neocarzinostatin chromophore A H 3 C OH pent-3-yn-1-ol

NOT pent-2-yn-5-ol

Cycloalkanes and cycloalkenes

cyclopropane

1,3-dimethylcyclohexane

H 3 CCH 3 cyclohexenebenzene • Cyclic hydrocarbons are common - note that most are not flat

Cyclic structures in nature

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• Ring systems are common in natural products & pharmaceuticals• Example below shows the importance of another form of isomerism -

stereoisomers 12 CH 3 CH 3 H 3 C H 3 C CHquotesdbs_dbs17.pdfusesText_23