Aldehydes & Ketones

Question 1

Suffix on aldehydes

Answer 1

-al

Question 2

What prefix is used when aldehydes are substituents

Answer 2

oxo-

Question 3

What suffix is used if the aldehyde is attached to a ring?

Answer 3

-carbaldehyde

Question 4

What suffix is used for ketones

Answer 4

-one

Question 5

What kind of bonding can aldehydes & ketones go though?

Answer 5

Dipole-dipole interactions

Question 6

What kind of reactant are aldehydes & ketones?

Answer 6

electrophiles

Question 7

Which are more polar, aldehydes/ketones or alcohols?

Answer 7

Aldehydes/ketones

Question 8

Nucleophilic Addition

Answer 8

Nucleophile attacks & opens carbonyl, if there is a good leaving group, the carbonyl can reform

Question 9

What can aldehydes & ketones form in the presence of water?

Answer 9

Geminal diols (1,1 / On the same carbon)

Question 10

What is the geminal diol formation called?

Answer 10

Hydration

Question 11

What is the nucleophile in hemiacetal/hemiketal formation?

Answer 11

1 equi of alcohol

Question 12

What is a hemiacetal/hemiketal

Answer 12

Formation of alcohol & acid from aledhyde/ketone

Question 13

What nucleophile is used for acetal/ketal formation?

Answer 13

2 equiv of alcohol

Question 14

What kind of reaction produces acetal/ketal

Answer 14

SN1

Question 15

Imine

Answer 15

A compound with a nitrogen atom double-bonded to a carbon atom

Question 16

What kind of reaction is imine formatiosonance n?

Answer 16

Condensation/Nucleophilic substitution

Question 17

What are common ammonia derivatives that react with aldehyde & ketones

Answer 17

Hydroxylamine, hydrazine, semicarbazide

Question 18

Enamines

Answer 18

Imines that undergo tautomerization (Double bond & a nitrogen-containing group

Question 19

Cyanohydrins

Answer 19

Reactions with aldehydes & ketones with hydrogen cyanide

Question 20

Can ketones form carboxylic acids?

Answer 20

NO

Question 21

Reducing agents for ketones & aldehydes

Answer 21

LiAlH4 & NaBH4

Question 22

a-carbon

Answer 22

Adjacent to carbonyl carbon & hydrogens connected to them are a-hydrogens

Question 23

Why are a-hydrogens so acidic?

Answer 23

Resonance stability of conjugate base

When hydrogen is removed, extra electons can resonate between a-carbon, carbonyl , carbonyl oxygen

Question 24

Carbanion

Answer 24

Negatively charged carbon atom that is helped to stabilize by electron-withdrawing oxygen

Question 25

Which alpha protons are more acidic, aldehydre or ketone?

Answer 25

Aldehyde (ketone has electron donating groups)

Question 26

What does the additional alkyl groups on the ketone cause?

Answer 26

Steric hindrance

Question 27

How do aldehydes & ketones exist in a solution?

Answer 27

Mixture of keto & enol forms due to the acidity of a- hydrogens

Question 28

Enol form

Answer 28

Carbon-carbon double bond & alcohol component

Question 29

Tautomers

Answer 29

Keto & enol forms that differ in placement of proton & double bond

Question 30

Enolization/tautomerization

Answer 30

Process of interconverting from keto-enol foms

Question 31

Which tautomer is thermodynamically favored?

Answer 31

Keto form

Question 32

a-racemization

Answer 32

Aldehyde or ketone with chiral a-carbon will rapidly become a racemic mixture as the forms interconvert

Question 33

What are common strong bases?

Answer 33

OH-, lithium disopropyl amide (LDA), Potassium hydride (KH)

Question 34

What can deprotonated enols be used as?

Answer 34

Nucleophiles if treated with strong base first

Question 35

Michael addition

Answer 35

Carbanion of dicarbonyl attacks an a,B-unsaturated carbonyl compound of a dicarbonyl

Question 36

Thermodynamic enolate

Answer 36

One connected to more substituted carbon

Question 37

Kinetic enolate

Answer 37

One connected to less substituted carbon

Question 38

Which product is favored in fast & irresversible?

Answer 38

Kinetic

Question 39

Which product is favored at low temperature?

Answer 39

Kinetic

Question 40

Which product is favored with strong, sterically hindered base?

Answer 40

Kinetic

Question 41

When is the thermodynamic product favored?

Answer 41

Slow, reversible, weaker & smaller bases

Question 42

Enamine

Answer 42

CC double bond attached to a amine

Question 43

Which is thermodynamically favored enamine or imine?

Answer 43

Imine

Question 44

Aldol condensation

Answer 44

Aldehyde/ketone acts as both an electrophile (keto form) and nucleophile (in enolate from) Ends in formation of CC bond

Question 45

Aldol

Answer 45

A carbonyl and OH groups combined bc of a combination of two acetaldehyde molecules with the enolate form attacking another carbonyl to form the alcohol group

Question 46

Dehydration of the aldol

Answer 46

Strong base & high temps will kick off a water molecule & form a double bond (E1 & E2) to make an a,B unsaturated

Question 47

What helps to specifically bind to one reactant?

Answer 47

Attack aldehyde or ketone that has no a-hydrogens (quatenary a-carbons like benzyladehyde)

Question 48

Retro aldol reaction

Answer 48

Aqueous base & heat to get back to aldehyde or ketone form