Carboxylic Acid Derivatives: Names + Rxns

functional group, prefix, suffix

• alcohol

• prefix: hydroxy-

• suffix: -ol

functional group, prefix, suffix

• Alkane

• prefix: alkyl-

• suffix: -ane

functional group, prefix, suffix

• amide

• prefix: carboxyl, amido-

• suffix: -amide

functional group, prefix, suffix

• anhydride

• prefix: alkanoyloxycarbonyl-

• suffix: anhydride

functional group, prefix, suffix

• carboxylic acid

• prefix: carbox-

• suffix: -oic acid

functional group, prefix, suffix

• alkene

• prefix: alkenyl-

• suffix: -ene

functional group, prefix, suffix

• alkyne

• prefix: alkynyl-

• suffix: -yne

functional group, prefix, suffix

• ester

• prefix: alkoxycarbonyl-

• suffix: -oate

functional group, prefix, suffix

• aldehyde

• prefix: -oxo

• suffix: -al

functional group, prefix, suffix

• ketone

• prefix: oxo-, keto-

• suffix: -one

steps to naming

1. ID highest priority functional group by ox state (total bonds to O or N); compound will be named by suffix of this group

2. # the longest consecutive carbon chain that contain’s highest priority group. highest priority group should receive lowest # possible

3. name the carbon chain

4. name constituents (non- priority functional groups) that are part of carbon chain with prefix

5. name compound by listing #’s in alphabetical order

rank reactivity of carboxylic acid derivatives (highest to lowest). what determines this order?

acid halides > anhydrides > carboxylic acid > esters > amides

• based on leaving group stability and charge

naming carbon chains based on # of carbons (1-8)

• 1 = meth-

• 2 = eth-

• 3 = prop-

• 4 = but-

• 5 = pent-

• 6 = hex-

• 7 = hept-

• 8 = oct-

REDOX

oxidation = increase in oxidation state = loss of e-

• increase in # of bonds to O, N, halides, + C

• decrease in # of bonds to H

reduction = decrease in oxidation state = gain of e-

• increase in # of bonds to H

• decrease in # of bonds O, N, halides, + C

ox or red: primary alcohol to aldehyde using PCC

oxidation

ox or red: secondary alcohol to ketone using CrO3/pryamidine

oxidation

ox or red: aldehyde to carboxylic acid using H2CrO4

oxidation

ox or red: aldehyde to primary alcohol using LiAlH4/NaBH4

reduction

ox or red: ketone to secondary alcohol using LiAlH4/NaBH4

reduction

ox or red: carboxylic acid to primary alcohol using 1.LiAlH4, ether/2. H2O

reduction

adding one equivalent of alcohol to an aldehyde produces? two equivalents?

1 equiv: hemiacetal

2 equiv: acetal

adding one equivalent of alcohol to a ketone produces? two equivalents?

1 equiv: hemiketal

2 equiv: ketal