Chapter 21 Flashcards by Hannah Hausmann

Carboxylic acid derivative

RC=OX

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X=-OR

Ester

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X=-NR2

Amide

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X=-X

Acid halide

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X=-COOR

Anhydride

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“Mono” acids

Take off E, add “oic acid”

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Mono acid with ring

Name it as ring, add carboxylic acid

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Formic acid r group

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Acetic acid r group

CH3

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Propionic acid r group

CH3CH2

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Butyric acid r group

CH3CH2CH2

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Benzoic acid R group

Phenol

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Diacids(with 2 carbocylic acid groups)

Use “dioic acid” as suffic

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Are carboxylic acids or similar alcohols more acidic? Why?

Carbox acids, conjugate bases are more stable

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What effect do electron withdrawing groups have?

Make conjugate bases more stable, make compounds more acidic

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Closer electron withdrawing groups

Increase acidity

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R triple bonded to R with 1. O3 2. H2O

2 RCOOH

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RCH3OH with Na2Cr2O7, H2SO4

RCOOH

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Phenol bound to isopropyl,Na2Cr2O7, H2SO4

Phenol bound to COOH

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R-C triple bound to N reacted with H3O+ and heat

RCOOH

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RMgBr reacted with CO2 and H3O+

RCOOH

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Reduction of acid yields an

Alcohol (LAH OR 1. BH3, THF 2. H2O2, NaOH can be used)

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To name an acid halide

Replace ic acid with yl halide

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Acid halide bound to ring

Carbonyl Xide

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Acid anhydride

Anhydride

Esters

Ate

Amide

amide

Amide bound to ring

Carboxamide

Nitrile

Onitrile

Least to most reactive

OH, NR2, OR, OCOR, Cl

The more stable the leaving group

The more reactive the compound is

If a reaction takes place in an acid

Don't form basic stuff

If a reaction takes place in a base

Don't form acidic stuff

What always happens?

NA, LLG

Is it easier to make things more or less reactive?

Less

What can make things more reactive?

SOCl2/COCl2 (replaces with Cl)

Acid halide with 1. LAH 2. H2O

RCH2OH

Acid halide with 1. LiA(o t butyl)3H 2. H2O

Aldehyde (H)

1. XS RMgBr

Replaces Everything with R

1. R2CuLi 2. H2O

Changes acid halide to ketone

Reactions with (RC(O))2)O- 1. 2 MECOOH with heat

Fuses them, water as byproduct

RCOCl with RCOO

Anhydride plus salt

Is (RC(O))2)O nucleophiles or electrophiles?

Electrophiles

RCOOR with 1. NaOH 2. MeI

Changes H to methyl group

HXO2 with ROH, py

RCOOR, pyr HCl

RCOOR with 1. NaOH 2. H3O+

RCOOH, ROH

RCOOR plus H3O+

RCOOH + MeOH

RCOOR plus NH3 and Heat

Amide

NC=O plus strong reducing agent

Alcohol

NC=O plus weak red agent

Aldehyde

RCOOR plus grignard

Trisub alcohol

Acid plus 1. 2 RLI 2. H3O+

Ketone

HXO2 plus 2 NH3

Amide

2CO joined by O plus 2RNH2

Amide

RCOOR plus RNH2 and heat

Amide

NC=O plus H3O+

Acid (RCOOH

NC=O plus 1. LAH 2. H2O

Amine

RCH2Br plus NACN

Switches Br with Cn

How do you turn an NC=O to a RCN

SOCl2

RCN plus acid

Amide

NC=O plus acid

Acid

RCN plus 1. NaOH, H2O 2. H3O+

Acid

RCN and grignard

Keton

RCN plus 1. XS LAH 2. H2O

Amine