+ ESTERIFICATION O C C C C C O C C C C C H H H H H OH H O H H H H H H

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+ ESTERIFICATION O C C C C C O C C C C C H H H H H OH H O H H H H H H

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+ ESTERIFICATION O C C C C C O C C C C C H H H H H OH H O H H H H H H THE DOTTED WHITE LINE SHOWS WHERE THE NEW BOND FORMS H H H H H C C C OH H O C C H H H H H PROPANOIC ACID ETHANOL O H H H H H C C C O C C H + HOH H H H H ESTER LINKAGE ESTERIFICATION IS AN EXAMPLE OF DEHYDRATION SYNTHESIS, WATER IS REMOVED, IS A PRODUCT ACID PART ALCOHOL PART ALCOHOL PART ACID PART ETHYL PROPANOATE

! ! + ADDITION (ALKENE) C C C C C C C C C C C C H H H H Br2 H H H H H 2-BUTENE (CNH2N) BROMINE H H H H REMEMBER EACH C HAS 4 BONDS, EACH H ONLY 1, EACH HALOGEN ONLY 1 + Br2 H C C C C H ! H H REMEMBER: The halogen MUST bond to carbons where the double bond was located 2,3 DIBROMO BUTANE H H Br H H H H H SAME AS H C C C C H H C C C C H ! H Br H H H Br Br H 2,3 DIBROMO BUTANE, THESE STRUCTURES ARE NOT ISOMERS, THEY ARE THE SAME, THE SINGLE BOND ROTATES.

+ + ADDITION (ALKYNE) C C C C C C C C C C C C H H Br2 H H H H H Br H H 2-BUTYNE(CNH2N-2) BROMINE H H + Br2 H C C C C H H H THE CIS AND TRANS ISOMERS ARE NOT INTERCHANGEABLE, THERE IS NO ROTATION OF DOUBLE BONDS 2,3 DIBROMO BUTENE H Br H H H + H C C C C H H C C C C H H Br H H Br Br H CIS ISOMER TRANS ISOMER

! + SUBSTITUTION (ALKANE) C C C C C C C C C C C C H H H H Br2 H H H H BUTANE(CNH2N+2) BROMINE H H H H + Br2 H C C C C H H H H H REMEMBER A MIXTURE OF ISOMERS MAY BE OBTAINED IN SUBSTITUTION. 2 BROMO BUTANE 1 BROMO BUTANE ! H H H H H H H H AND H C C C C H H C C C C H H H H Br H Br H H HBr

C4H10O ISOMERS OF C4H10O C C C C C C O C C C C C C H H H H H OH H H H 1-BUTANOL C4H10O H H H H H H H H C C O C C H H C C C C H H H H H H H OH H H DIETHYL ETHER 2-BUTANOL

C4H10O ISOMERS OF C4H10O C C C C H CH3 C C C C CH3 C CH3 PRIMARY H H H OH H H H H 1-BUTANOL C4H10O TERTIARY H H 1 CH3 1 C H H H 4 C 3 C 2 C 3 CH3 C OH H OH 2 H H SECONDARY CH3 2-BUTANOL 2-METHYL-2 PROPANOL