CARBONYL GROUP vs ACYL GROUP - structure? - hybridization of each atom?

CARBONYL: C=O - sp2 carbon - sp2 oxygen oxygen has 4 lone pairs -- ACYL: R - C = O - sp2 carbon - sp2 oxygen oxygen has 4 lone pairs basically bigger picture si acyl group

CARBONYL COMPOUNDS - 2 categories that are based on ___? + how are they different according to this classification

based on kinds of chemistry they undergo: 1. aldehydes and ketones - nucleophilic addition rxns - bonded to H or C atoms that CANT stabilize (-) charge 2. carboxylic acids and derivatives - nucleophilic substitution rxns - bonded to O or N or X atoms that CAN stabilize (-) charge thus, O;N;X can act as a leaving group in substitution rxns

ALDEHYDE - NOMENCLATURE 1. common name 2. IUPAC

1. named as derivatives of carboxylic acid however, change "-ic acid" to "-aldehyde" (formaldehyde) 2. - 1 COH: Alkanal / Alkenal / Alkynal - 2 COH: Alkanedial / Alkenedial / Alkynedial (methanal; butynedial)

ALDEHYDE - NOMENCLATURE - common names of linear carboxylic acid derivatives (5)

1. Formic Acid (Methanoic Acid) 2. Acetic Acid (Ethanoic Acid) 3. Propionic Acid (Propanoic Acid) 4. Butyric Acid (Butanoic Acid) 5. Valeric Acid (Pentanoic Acid)

KETONES - NOMENCLATURE 1. common name 2. IUPAC 3. cyclic ketones 4. special ketones

1. - mention the 2 alkyl groups attached to the O atom (alphabetical order) + "ketone" - if identical = add prefix (di-) (methyl propyl ketone; dimethyl ketone) 2. - 1 ketone group: Alkanone - 2 ketone groups: Alkanedione same with alkene, alkyne (3-hexanone ; 1-peneten-3-one) 3. - position 1 automatically assigned to carbonyl carbon atom (3-bromocyclohexenone) 4. using phenone group (acetophenone ; benzophenone)

ALDEHYDES & KETONES Preparation - 4 ways?

1. Ozonolysis of Alkenes 2. Hydration of Alkynes 3. Oxidation of 1° and 2° alcohols 4. Friedel-Crafts Acylation

ALDEHYDES & KETONES Reactions - 5 (main)

1. Oxidation of Aldehydes 2. Reduction 3. Nucleophilic Addition 4. Haloform Reaction 5. Aldol Condensation

ALDEHYDES, KETONES, CARBOHYDRATES Flashcards by Fiara Arnaldo

CARBONYL GROUP

ACYL GROUP

structure?
hybridization of each atom?

CARBONYL:
C=O

sp2 carbon
sp2 oxygen
*oxygen has 4 lone pairs

–

ACYL:
R - C = O
- sp2 carbon
- sp2 oxygen
*oxygen has 4 lone pairs

*basically bigger picture si acyl group

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CARBONYL COMPOUNDS

2 categories that are based on ___?

+ how are they different according to this classification

based on kinds of chemistry they undergo:

aldehydes and ketones
- nucleophilic addition rxns
- bonded to H or C atoms that CANT stabilize (-) charge
carboxylic acids and derivatives
- nucleophilic substitution rxns
- bonded to O or N or X atoms that CAN stabilize (-) charge

thus, O;N;X can act as a leaving group in substitution rxns

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ALDEHYDE - NOMENCLATURE

common name
IUPAC

named as derivatives of carboxylic acid
*however, change “-ic acid” to “-aldehyde”

(formaldehyde)

- 1 COH: Alkanal / Alkenal / Alkynal
- 2 COH: Alkanedial / Alkenedial / Alkynedial

(methanal; butynedial)

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ALDEHYDE - NOMENCLATURE

common names of linear carboxylic acid derivatives (5)

Formic Acid (Methanoic Acid)
Acetic Acid (Ethanoic Acid)
Propionic Acid (Propanoic Acid)
Butyric Acid (Butanoic Acid)
Valeric Acid (Pentanoic Acid)

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KETONES - NOMENCLATURE

common name
IUPAC
cyclic ketones
special ketones

- mention the 2 alkyl groups attached to the O atom (alphabetical order) + “ketone”
- if identical = add prefix (di-)

(methyl propyl ketone; dimethyl ketone)

- 1 ketone group: Alkanone
- 2 ketone groups: Alkanedione
  *same with alkene, alkyne

(3-hexanone ; 1-peneten-3-one)

- position 1 automatically assigned to carbonyl carbon atom

(3-bromocyclohexenone)

using phenone group

(acetophenone ; benzophenone)

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in nomenclature, do u need to mention the position number of the functional groups for aldehydes and ketones?

for ketones, yes

for aldehydes no kasi aldehyde has an H atom connected to the carbonyl C so automatic it would be located at the end

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in nomenclature, how is the parent chain numbered?

always include the carbonyl C in numbering

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ALDEHYDES & KETONES

Physical Properties - Polarity

polar due to carbonyl group
more polar than ethers

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ALDEHYDES & KETONES

Physical Properties - Bonds & Interactions

dipole-dipole interaction in pure state
hydrogen bonds with water

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ALDEHYDES & KETONES

Physical Properties - Boiling Point

Higher BP than non polar compounds
lower BP than alcohols / carboxylic acids

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Arrange the ff in INCREASING BP

Alkenes, Ethers
Alcohols
Aldehydes, Ketones

Alkenes, Ethers < Aldehydes, Ketones < Alcohols

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ALDEHYDES & KETONES

Physical Properties - Solubility

soluble in H2O (only for carbonyl compounds with <5 C atoms)
soluble in organic solvents

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ALDEHYDES & KETONES

Preparation

4 ways?

Ozonolysis of Alkenes
Hydration of Alkynes
Oxidation of 1° and 2° alcohols
Friedel-Crafts Acylation

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ALDEHYDES & KETONES

Reactions

5 (main)

Oxidation of Aldehydes
Reduction
Nucleophilic Addition
Haloform Reaction
Aldol Condensation

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ALDEHYDES & KETONES

Reactions - Nucleophilic Addition
- 4 types?

Addition of HCN
Addition of Alcohols
Addition of Grignard’s Reagent
Addition of derivatives of NH3

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do ketones undergo oxidation?

Study These Flashcards

no, they are resistant for some reason

ALDEHYDES & KETONES

Reactions - Oxidation of Aldehydes

2 sets of reagents?
examples for each (3)?
difference in terms of products? + general reaction

Study These Flashcards

1ST SET: common oxidizing reagents

1.) CrO3, H2SO4 (Jone’s Reagent)
2.) K2Cr2O7, H+
3.) hot acidic KMnO4

aldehyde -> carboxylic acid

R-C-H -> R-C-OH

2ND SET: basic reagents

1.) Ag(NH3)2+ = Tollen’s Reagent
2.) [Cu(citrate)2] ^ 2- , -OH = Benedict’s Reagent
3.) [Cu(tartrate)2] ^ 2- , -OH = Fehling’s Reagent

NO.1:
aldehyde -> ammonium carboxylate

R-C-H -> R-C-O-+NH4

NO.2-3:
aldehyde -> carboxylate

R-C-H -> R-C-O-

4 tests for aldehydes

+ positive reaction

Study These Flashcards

Tollen’s Test
- silver mirror formation
Benedict’s Test
- brick red ppt
Fehling’s Test
- brick red ppt (redder)
Jones’ Test
- opaque green ppt

ALDEHYDES & KETONES

Reactions - Reduction Reactions

2 sets of reagents?
examples for each (3 ; 2)?
difference in terms of products (for both aldehyde & ketone)? + general reaction

+ palatandaan?

Study These Flashcards

1ST SET: common reagents

1.) H2, Pd/Pt/Ru/Raney Ni -> High P

2.) NaBH4, H2O

3.) 1. LiAlH4, dry ether -> 2. H3O+

*aldehyde -> 1° alcohol
RHC = O -> RHC-OH

*ketone -> 2° alcohol
R2C = O -> R2C-OH

2ND SET: basic reagents
- carbonyl group becomes methylene group

1.) NH2NH2, -OH, heat
2.) Zn(Hg), conc. HCl

*aldehyde -> alkane
RHC = O -> RH3C

*ketone -> alkane
R2C = O -> R2H2C

ALWAYS SHOW ALL THE HYDROGEN ATOMS SINCE KASAMA SIYA SA REACTION

reagents for

wolff-kishner reaction
clemmensen reaction

+ what reaction can this be found?
+ difference

Study These Flashcards

1.) NH2NH2, KOH, heat
- for compounds sensitive to acid

2.) Zn(Hg), conc. HCl
- for compounds sensitive to base

*reduction reactions

ALDEHYDES & KETONES

Reactions - Nucleophilic Addition

ADDITION OF HCN
- other term?
- reagents (2)?
- when will slow reaction occur?
- general reaction? + products (2)

Study These Flashcards

cyanohydrin formation

NaCN, HCl
KCN, HCl

slow reaction when pure HCN is used (weak acid)

carbonyl group -> cyanohydrin

C=O -> NC-C-OH + -:CN

ALDEHYDES & KETONES

Reactions - Nucleophilic Addition

ADDITION OF ALCOHOLS
- other term?
- reagent (1)?
- general reaction? + products (2)

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hemiacetal/hemiketal and acetal/ketal formation
alcohol, dry HCl

carbonyl ->* hemiacetal/ketal -* acetal/ketal

*all -> undergo alcohol, dry HCl reagent

C=O -> R’OH, dry HCl -> R’O-C-OH (hemiacetal/ketal)

-> R’OH, dry HCl -> R’O-C-OR’ (acetal/ketal)

all the OR’ that will attach to carbonyl carbon will be based on the alcohol reagent

acetal vs ketal

Study These Flashcards

acetal = from aldehyde

ketal = from ketone

ALDEHYDES & KETONES

Reactions - Nucleophilic Addition

ADDITION OF GRIGNARD REAGENT

what serves as the Nu?
net addition of ___ via the strong NU
reagents (2)?
general reaction? + products (2)

Study These Flashcards

carbanion (R-) from grignard reagent (RMgX)
net addition of R-H

REAGENTS
*consecutive (2 arrows)
R’MgX -> dry ether
THEN H3O+

C=O -> R’ - C - OH + MgX

*so basically mawawala lang si double bond O and kakabit yung R’ from grignard and OH

ALDEHYDES & KETONES Reactions - Nucleophilic Addition ADDITION OF DERIVATIVES OF NH3 - reagents (4)? - general reaction? + products (2)

REAGENTS: G-NH2 1.) NH2-R 2.) NH2-OH 3.) NH2-NH2 4.) NH2-NH-Carbonyl-NH2 C=O -> C=N-G +H2O *remove 2 hydrogen atoms from G-NH2 so ang matitirang kakabit ay N-G

ALDEHYDES & KETONES Reactions - Nucleophilic Addition ADDITION OF DERIVATIVES OF NH3 - DETERMINE the name of the reagent and product after being substituted to the carbonyl group 1.) NH2-R 2.) NH2-OH 3.) NH2-NH2 4.) NH2-NH-Carbonyl-NH2

1. Amine - imine 2. Hydroxylamine - oxime 3. Hydrazine - hydrazone 4. Semicarbazide - semicarbazone

DETERMINE THE TEST - for all aldehydes and ketones? - reagent? - positive result?

2,4-DNP Test - 2,4-dinitrophenylhydrazine in H2SO4 - formation of yellow-orange ppt

DETERMINE THE TEST - for methyl ketones, acetaldehyde, and 2° methyl alcohols? - reagent? - positive result?

IODOFORM TEST - I2/KI, NaOH - Formation of yellow ppt (iodoform)

ALDEHYDES & KETONES Reactions - Haloform Reaction - oxidation of a ____ ___ by a _____ to form a ____ and ______ - other term? - reagents (2)? - general reaction?

- methyl ketone - hypohalite - carboxylate - haloform - iodoform test 1.) excess X20> NaOH 2.) I2/KI, NaOH methyl ketone -> carboxylate + haloform RCH3-C=O -> RO(-) - C = O + CHX3

Palatandaan in Haloform RXNS?

- must be a methyl ketone

what is alpha carbon?

carbon attached to the carbonyl carbon (carbon connected to the O thru double bond)

Acidity of Alpha Hydrogens - occurs due to? - thus... the alpha hydrogens can be?? - once abstracted, the resulting carbonyl compound becomes? - ^^ which can?

- carbonyl carbons - can be abstracted by bases - an enolate ion - can acts as Nu in nucleophilic addition reactions

how to know if a compound is enolizable or not?

has at least ONE alpha- hydrogen

ALDEHYDES & KETONES Reactions - Aldol Condensation - general steps (2) - shortcut to overall reaction (3)? - how many products overall?

1. Enolate ion attacks another carbonyl group to form an ALDOL (β-hydroxy carbonyl compound) 2. Aldol undergoes DEHYDRATION to produce (α,β-unsaturated carbonyl compound) *basically: 1. a carbonyl group will lose an alpha hydrogen to become an enolate ion 2. the C(-) in the enolate ion will lose 2 HYDROGEN ATOMS in total 3. the enolate ion (losing 2 H atoms) will substitute the =O of the carbonyl group --- CASE: 1.) 2 molecules of the same carbonyl group = 2 products 2.) enolizable carbonyl group + another enolizable carbonyl group = 4 products 3.) enolizable carbonyl group + UN-enolizable carbonyl group = 1 product

ALDEHYDES, KETONES, CARBOHYDRATES Flashcards

(34 cards)