11/2/2009

Overview

Survey of Key Functional Groups

Ch 8.1

Chem 201 – Functional Group Survey 11/2/2009

Overview Overview

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

1 11/2/2009

Concerns Functional Group Names

 Getting overwhelmed Alcohol  Strange new formulas  Strange new names  Strange new reagents Alkyl halide, Haloalkane  Many new relationships  leads to brain meltdown !!!

 Info builds ONE step at a Thiol time  Ch 8 surveys FG  Names, drawings, properties  No new reactions (almost) Ether Sulfide

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

RX Names Common or Substitutive (IUPAC)? Special Compounds Use Common Names  Alkyl halide  Haloalkane Haloforms  Alkyl group attached  Halogen substitutent methylene chloride  to Halogen  attached to Alkane chloroform ()(dichloromethane) bromoform  Methyl chloride  Chloromethane iodoform  Ethyl bromide  Bromoethane

Useful solvents  Special compounds carbon tetrachloride - hydrophobic  Special groups - moderately polar carbon tetrabromide - volatile  methylene, allyl, vinyl, benzyl but all linked to health problems  Special history allyl bromide these slides will be posted

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

2 11/2/2009

Give “haloalkane” (IUPAC) names Give “haloalkane” (IUPAC) names

2- fluoropropane

cis-121,2-dibromocycl o hexane

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

ROR’ Names ROR’ Names Common & Substitutive Additional considerations

  Dialkyl ether Alkoxyalkane 1,2-dimethoxyethane  2 Alkyl groups attached  Alkoxy (RO) substitutent  to oxygen make Ether  attached to Alkane (R’) Tetrahydrofuran Many special rings (THF) furan  Diethyl ether (“ether”)  Alkoxy = alkyl (R) + oxy  Methyl tert-butyl ether  Alkane = alkyl (R’) + ane (MTBE) oxirane  EhEthoxyet hane epoxide “alkene” oxide  2-Methoxy-2-methylpropane

1,4-dioxane anisole

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

3 11/2/2009

RSR’ Names Common & Substitutive RX, ROR’, RSR’ name similarities

 Dialkyl sulfide  (Alkylthio)alkane  Common names used widely  2 Alkyl groups attached  Alkylthio (RS) substitutent  Special compounds (names often break “common” rules)  to slfrsulfur make Sulfide  attached to Alkane (R’)  Ring s (ROR, RSR onl y)

 Alkylthio = alkyl (R) + thio  IUPAC  Alkane = alkyl (R’) + ane  Substituted alkane  Haloalkane  Alkoxyalkane ethyl methyl sulfide  (Alkylthio)alkane

(methylthio)ethane

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

ROH, RSH name similarities Alcohol names - common or IUPAC?

 Common names used  Common names are fading out  Special compounds  Special groups

 IUPAC  New suffix replaces “alkane” allyl alcohol benzyl alcohol  ROH, alkanol  RSH, alkanethiol  Special compounds

ethylene glycol glycerol Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

4 11/2/2009

IUPAC - Alkanol IUPAC - Alkanethiol

 Parent chain = longest chain bearing OH  Parent chain = longest chain bearing SH  Alkanol = alkane + ol  Keep ‘e’ from alkane Parent = alkanol Parent = alkanethiol  # = pos it ion of OH  Add ‘thio l’ (o ne wo rd)   give smallest # possible 2-chlorocyclopentanol # = position of SH  always #1 in ring cis-2-chlorocyclopentanol  give smallest # possible (1R,2S)-2-chlorocyclopentanol Common  always #1 in ring

4-methyl-3-penten-1-ol

tert-butyl mercaptan 2-pentanol 1,2-ethanediol 2-pentanethiol pentan-2-ol ethane-I, 2-diol pentane-2-thiol

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

When groups compete: alcohol vs. thiol IUPAC Rules (p. 327)

1. Identify the principal group  How would you name this? a. Rank candidates (OH beats SH) 2. Identif y the priilincipal chhiain  5 C chain. Could be… a. Chain contains principal group(s)  some kind of I-pentanol b. Chain contains max. number double & triple bonds, etc.  some kind of 2-pentanethiol 3. Number the principal chain  Who wins? OH or SH? a. Lowest # for C bearing principal group  And how do yygpou name other group as substituent? b. Lowest # for multiple bonds, etc. 4. Construct name  IUPAC Rules !!! a. Name principal chain, group, and # b. Name substituents and #’s

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

5 11/2/2009

But IUPAC rules are problematic Chem 201 simplification

 Complicated  I will only give you naming problems for compounds  Must fill in etc. (several rules) that contain ONE principal group  MstMust know princi rincialpal group rankings  YoYou u dond o n ’t need to learn principal group rankings  Must know substituent names  You don’t need to learn substituent names

OH O

SH 6-hydroxy-7-mercaptooctan-4-one  And IUPAC names are not even universally accepted  But … I will expect you to be able to work with more complicated names when I provide them

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

Typical naming problems Typical naming problems

 Draw 5-(ethylthio)-2-methylheptane  Draw 5-(ethylthio)-2-methylheptane

 Draw an oxirane  Draw an oxirane

Chem 201 – Functional Group Survey 11/2/2009 Chem 201 – Functional Group Survey 11/2/2009

6