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Chem 223 > Chap 2 > Flashcards

Chap 2 Flashcards

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1
Q

Secondary alcohol with strong oxidants

A

Ketone

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2
Q

Primary alcohol with strong oxidants

A

Hydrate then carboxylic acid

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3
Q

Primary alcohol with Pcc and ch2cl2

A

Aldehyde

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4
Q

Ketone With mcpba

A

Ester

O on most stable (+ side)

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5
Q

Carboxylic acid with 1/2 alcohol

A

Fischer esterification
Ester

3 alcohols don’t work

Reversible

Acidic activation

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6
Q

2 carboxylic acids with p2o5, p4o10 in ch2cl2

A

Anhydride

Same r groups on either side, can be internal

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7
Q

Carboxylic acid with Pcl5

A

Acyl chloride

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8
Q

Carboxylic acid with pcl3

A

Acyl chloride

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9
Q

Carboxylic acid with socl2

A

Acyl chloride

Needs to be anhydrous

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10
Q

Can amides be formed from carboxylic acids?

A

No

Acid base reaction

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11
Q

Ester plus water (hydrophobic or hydrophilic)? H2so4 activation

A

Produces carboxylic acid and alcohol, acidic mechanism

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12
Q

Ester plus NaOH (with Etoh and h2o with heat)

A

Carboxylic acid and alcohol

Basic mechanism (hydrophobic esters)

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13
Q

Amide with NaOH (etoh/h20/heat)

A

Carboxylic acid and ammonia

Irreversible

Basic mechanism

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14
Q

Amide with h2o (h2so4/heat)

A

Carboxylic acid and r group ammonia (r on nh if applicable)

Acidic mechanism

Irreversible

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15
Q

R-cN with water (h2so4/heat)

A

Carboxylic acid (ammonium ion)

Reversible (nitrile hydrolysis)

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16
Q

Acyl chloride with carboxylic acid

A

Anhydride (can be dissymmetrical r groups)

17
Q

Acyl chloride with an alcohol with a Et3N or pyridine

A

Sacrificial base

Ester formation

Alcohol could react with h that’s why sacrificial base

Works for ALL ROH not just Fischer esterification

18
Q

Acyl chloride plus nh2 or nhr2

A

Amide

Dry/ch2cl2

Sacrificial base needed

19
Q

Anhydride with carboxylic alcohol

A

Ester

2 oh group

No need for sacrificial base

20
Q

Ester plus alcohol under acidic conditions

A

Trans esterification (swap r groups on 0-r side of ester)

21
Q

Reduction of any carboxylic acid derivative is with liah4 thf and h30 workup gives what

A

Primary alcohol

22
Q

Amide reduction with liah4 and h30+ workup gives what

A

R-CH2-N-r groups

23
Q

Ester reduction gives what

A

Alcohol from each side of ester ( 1 primary on c=o side)

24
Q

Acyl reduction gives what

A

Primary alcohol with cl

25
Q

How to stop at aldehyde stage of reduction

A

Must use acyl chloride

Cool temperature

Dry thf

Tuned down Version of liah4

26
Q

Ester with organomagnesium or organolitihium with thf and h3o work up

A

Tertiary alcohol with 2 identical r groups

Irreversible

27
Q

To stop at ketone stage with ester reduction by alkylation

A

option 1

Carboxylic acid with r-Li

Option 2

Acyl chloride with organocuperate (-78 degrees) thf

Option 3

Nitrile with organo magnesium

28
Q

Co2 In default

Organometallic in excess

A

3 alcohol with 3 identical r groups

Following acidic works up

29
Q

Organometallic in default

Excess co2

A

Carboxylic acid ( with r group from grignard) then acidic workup

Chem 223 (1 decks)

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