55 Flashcards by Hannah Hausmann

Q

Ketone to enolate

A

Base

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Q

Cold reaction

A

Less substituted

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Q

Hot reaction

A

More sub

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Q

How to retrosynthesize aldol

A

Break 2x bond, both pieces have O

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Q

Does XCuLi add at alpha or beta

A

beta

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Q

What does h3O+ and heat do to ester?

A

Removes one COOR

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Q

How to retrosynthesize ester

A

Cut between base and alpha

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Q

Br to Alpha

A

Br, H3O+ (mark)

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Q

How do you remove Br?

A

Base

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Q

How do you brominate carboxylic acid

A

Br, PBr3
H2O

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Q

Brominating under basic conditions

A

NaOH, Br2

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Q

Aldol condensation

A

Aldehyde treated with base and water

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Q

Cold condensation

A

Leaves OH on

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Q

Hot condensation

A

Takes OH off

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Q

Intramolecular aldol

A

NaOH, Heat

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Q

Claisen condensation fuses

A

Ester, taking off one r group

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Q

Claisen condensation reagents

A

NaOEt
H3O+

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Q

Intramolecular claisen

A

NaOEt
H3O+

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Q

Adding R group to ketone

A

LDA 2. RX

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Q

Thermodynamic

A

DB in more sub place

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Q

Kinetic

A

DB in less sub place

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Q

Adding R to ester

A

NaOET
RX

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Q

Michael Acceptor

A

Has DB

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Q

Adding R group to dienolate

A

LDA
Alkene
H30+

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Adding R to enolate

1. R2NH, H+ (-H2O)

Fusing dienol and aklene with 2 bonds

1. NaOH 2. NaOH, heat

To form a 1, 3 dicarbonyl compound

Use claisen (1. NaOET 2. H3O+)

To form a 1, 5 dicarbonyl

Use a michael (R2NH, H+, -H2O 2. Alkene 3. H2O)

Polyalkylating a keton

1. 2x NaOEt 2. 2 RX 3. H3O+

Enolate

Extra LP

Enolate with H2O

Enol

Enolate with RX

Adds R

DIacid suffic

Dioic acid

Cut carbox acid

1. O3 2. H2O

Oxidize alcohol to make

Carbox acid

Ox alkylbenzene

Carbox acid

Nitrile (CN) to carbox acid

H3O+, heat

Grignard to carbox acid

1. CO2 2. H3O+

Acids are reduced to

Alcohol (LAH or 1. BH3, THF 2. H2O2, NaOH)

Acid halide suffix

yl halide

Acid anhydride (RCOOCOR

Anhydride

Ester suffix

ate

Amide suffix

Amide

Carbox acid attached to a ring suffix

Carboxamide

CN siffix

Onitrile

Adding Rs to RCOX

1. XS RMgBr 2. H2O

Adding R to RCOX

1. R2CuLi 2. H2O

Fusing acid anhydrides to make acetic anhydride ch3coococh3

CCOOH (Heat)

Fusing acid chloride

RCOO-, Na+

Make ester from carbox acid

1. NaOH 2. MeI

FISCHER MECHANISM

Acid chloride to ester

ROH, Pyr

Ester to carbox acid

1. NaOH 2. H3O+

Ester (RCOOMe- swap me for NH2)

NH3, Heat

Amide (RCONH2_ to carbox acid

H3O+, heat

Amide(RCONH2_ to amine

1. XS LAH 2. H2O

Amide (RCONH2) to nitrile (RCN)

SOCl2

Hydrolyzing nitriles gives you ___________. Hydrolyzing that gives you _________________.

Amide (NH2), carbox acid (OH

Nitrile to Acid

1. NaOH, H2O 2. H3O+

Nitrile to keton

1. RMgBr 2. H3O+