Organic Chem Final Purdue 255

Alcohol

-OH (hydroxy group)

Alkyne

triple bond

Amide

-CONH2, -CONHR, -CONR2

Amine

-NH2 (amino group)

Anhydride

Arene

aromatic ring

Carboxylic acid

-COOH

Ester

-COOR

Ether

-OR (alkoxy group)

Ketone

-C=O (carbonyl group)

hydroxyl

R-OH

Ketone

RCOR

Thiol

R-SH

Sulfide

R-S-R

number of carbons and higher surface area

______ increases the boiling point

constitutional isomers

same molecular formula but different connectivity

stereoisomers

same molecular formula, same connectivity, different orientation

enantiomers

stereoisomers that are non-superimposable mirror images

diastereomers

stereoisomers that are not mirror images

meso compounds

superimposable mirror images

acidity trends

down and to the right of periodic table ; stronger acid

hydrohalogenation reaction

adds HI, HBr or HCl across double bond

acid catalyzed hydration reaction

adds water across double bond

halogenation reaction

Br2 or Cl2 , creates enantiomers

halohydrin formation reaction

Br2 or Cl2 + H2O or ROH

substitution of alkanes reaction

Br2 or Cl2 and light or heat

allylic substitution reaction

Br2 or Cl2 or NBS or NCS and light or heat

antimarkovnikov halogenation

HBr + peroxides + light

SN2 reaction

requires good Nucleophile, no carbocation rearrangement, best w primary alkyl halides

SN1

best with tertiary alkyl halides, NEVER with primary, poor nucleuphile,

E2

requires good base, best w secondary and tertiary

E1

best with tertiary, poor base

deprotonation of alkynes

NaH2, NaH or LDA

acetylene + base +

making alkynes from acetylene

making alkynes from dibromides

dibromide + NaNH2

vicinal

on carbons next to each other

germinal

on the same carbon

halogenation

Br2 or Cl2

hydrohalogenation

HBr or HCl

hydroboration-oxidation of alkynes

terminal alkynes need (sia)2BH or 9BBN , internal alkynes need BH3

Conversion of alcohols to alkyl halides

HCl, HBr, HI

conversion of alcohols to alkyl chlorides

SOCl2, pyridine or Et3N

conversion of alcohols to sulfonates

MsCl or TsCl with pyridine or Et3N. converts OH to good LV group

acid catalyzed dehydration

H2SO4 , heat

pinacol rearrangement

H2SO4, need vicinal diol starting material

williamson ether synthesis

best with methyl or primary halides

acid-catalyzed addition of alcohols to alkenes

epoxide formation from alkenes

epoxide formation from halohydrins

nucleophilic epoxide ring opening

acid-catalyzed epoxide ring opening

regioselective

when the two possible products are constitutional isomers

stereoselective

two possible products are stereoisomers