VIDEO EXAMPLE OF SUBSTITUTION The hydrolysis of t-butyl halides They’re often easy/fast (facile) Done at room temperature Details of solvent optimize rates Qualitative nature of RX Substitutions…

Reactions of RX round robin What class of reaction is shown below ?: ELIMINATION The general reaction form below is what class of reactions ? R-X + Y - ---> R-Y + X - (nucleophilic) SUBSTITUTION

CH 3 CH 2 Br + HS - freons CH 3 CH 2 SH +Br- Is an example of what class of reactions? substitutions What class of compound is the one on the right, just above ? An ether (R-O-R’) What class of compound is the one on the right, just above ? An ester (RCOOR’)

What class of compound is the one on the right, above ? An amine (tertiary type) What is the class of reactions illustrated in the reaction just above ? Elimination Only product

Name two organometallic reactions that lead to bigger molecules Corey-House and Grignard Which of the two reactions above leads to alcohols ? Grignard Which of the two reactions above uses Li ? Corey-House What other metal compound is used in a Corey-House? CuI Grignard Reagent Mg In dry ether What is product of this reaction ? What class of compounds does Corey-House create ? Larger alkanes

Be specific !! + KOH/ ethanol HCl/H 2 SO 4 Peroxides reflux Kind of addition ?? Anti-Markovnikoff

Fill in from right to left (retrograde synthesis) Mg o Dry ether NBS CCL 4 /uv light Name this site Allylic site My class name? halohydrin

Alkyl halides commonly undergo substitution, organometallic addition and _________________ reactions Elimination (boom) H2OH2O What class of compounds am I ?? Thiol (also called a mercaptan) What class of reaction is this undesirable event ? Reduction reaction (makes H 2 or removes O from substrate)

Using the `hints’ …list the common classes (by name) of compounds that can be made from alkyl halides. *Made from alkoxide salts ethers *RX + + Na - O-C=O | R esters *Makes essence of skunk; uses H 2 S and relatives thiols (mercaptans) *With NH 3, NH 2 R, NHR 2 amines *Add KOH and ethanol to make… alkenes *Add KOH/aqueous to make Alcohols (same size)

…list the common classes (by name) of compounds that can be made from alkyl halides (continued) *with Mg/ dry ether, then carbonyls, then H+/H 2 O (bigger) alcohols *Li, then CuI and another RX all in dry ether (bigger) alkanes *Starts with a poisonous sodium salt + RX Cyanides (R-CN) *What two classes of substrates are used to make alkyl halides ? Alcohols & Alkenes *Any day doing organic chemistry … SUCKS SNOT!!  Is a good day

Is it too late to drop this class ??