PHOrgChem (Lecture) | Module 8 (Part 1: ALDEHYDE, and KETONE)

Carboxylic Acids, Acid Chlorides, Esters, Amides, and Anhydrides

Class 1 Carbonyl Compounds

Carboxylic Acid Derivatives

Class 1 Carbonyl Compounds are also known as?

Class 1 Carbonyl Compounds

These compounds are derived from the carboxylic acid and have a carbonyl group (C=O) attached to a special group that can leave easily in the reaction (leaving group).

Class 1 Carbonyl Compounds

Because of this leaving group, this class usually goes through reactions where something replaces the group attached to the carbonyl carbon.

Nucleophilic Acyl Substitution

Class 1 Carbonyl Compounds commonly undergo?

-OH

LEAVING GROUP (Z) of CARBOXYLIC ACIDS

-Cl

LEAVING GROUP (Z) of ACID CHLORIDES

-OR’

LEAVING GROUP (Z) of ESTERS

-NH2, -NHR, -NR2

LEAVING GROUP (Z) of AMIDES

-OCOR

LEAVING GROUP (Z) of ANHYDRIDES

Aldehyde, and Ketone

Class 2 Carbonyl Compounds

Class 2 Carbonyl Compounds

These class of compounds also have a carbonyl group (C=O) but instead of a leaving group, the carbon is bonded to hydrogen or carbon atoms only.

Class 2 Carbonyl Compounds

These compounds do not easily go substitution (since they lack the leaving group), instead they react by adding things to the carbonyl carbon known as NUCLEOPHILIC ADDITION

Nucleophilic Addition

Class 2 Carbonyl Compounds undergo?

Class 2 Carbonyl Compounds

These compounds are generally more reactive than the other class compounds because there is no stabilizing group attached

Class 1 Carbonyl Compounds

KEY DIFFERENCE BETWEEN CLASS 1 AND CLASS 2 COMPOUNDS: have a group that can leave, other atoms can take its place

Class 2 Carbonyl Compounds

KEY DIFFERENCE BETWEEN CLASS 1 AND CLASS 2 COMPOUNDS: don’t have a group that can leave, new atoms just add unto them.

Aldehyde, and Ketone

Organic compounds containing a carbonyl group (C=O)

Aldehyde

The carbon in the carbonyl group is bonded to at least one hydrogen atom

Aldehyde

General formula: R-CHO, where R is a hydrogen or an organic group. Found at the end of a carbon chain.

Aldehyde

Typically reactive and can be oxidized to carboxylic acids

Carboxylic Acid

Aldehyde typically reactive and can be oxidized to?

Aldehyde

Often have distinct odors and are found in nature (e.g., citrus oils, cinnamon)

Aldehyde

Used in industrial processes, perfumes, and pharmaceuticals

Aldehyde

Higher boiling points than alkanes of similar molecular weight

Alkanes

Aldehyde have higher boiling points than _______ of similar molecular weight

Aldehyde, and Ketone

Lower boiling points than alcohols (no hydrogen bonding between molecules)

Aldehyde

Soluble in water (especially small aldehydes) due to hydrogen bonding with water

Small Aldehydes

Aldehyde are soluble in water especially?

Aldehyde

Distinct odors – often sharp, or pleasant

Sharp to Sweet, or Pleasant

Odor of Aldehyde

Aldehyde

Undergo nucleophilic addition reactions (e.g., with water, alcohols, or amines)

Nucleophilic Addition Reaction

Aldehyde undergo this reaction wth water, alcohols, or amines

Aldehyde

Easily oxidized to form carboxylic acids

Aldehyde

Can be reduced to primary alcohols using reducing agents (e.g., NaBH₄)

Primary Alcohols

Aldehydes can be reduced to __________ using reducing agents like Sodium borohydride

Aldehyde

React with Tollens' and Fehling's reagents, giving positive test results

Tollen’s, and Fehling’s Reagent

Aldehyde react with these reagents, giving POSITIVE test results

Aldehyde

Act as electrophiles due to the partial positive charge on the carbonyl carbon

Elecrtrophiles

Aldehyde act as _______ due to the partial positve charge of the carbonyl carbon

C3H4O

Chemical Formula of Acrolein

Colorless to Pale Yellow Liquid

Appearance of Acrolein

Strong Unpleasant/Pungent

Odor of Acrolein

Aldehyde

Source: Produced by the oxidation of glycerol or by the combustion of organic materials

52.5 C

Boiling of Acrolein in Celcius

126.5 F

Boiling of Acrolein in Fahrenheit

Acrolein

Solubility: Miscible with water, ethanol, and ether

Water, ethanol, and ether

Acrolein is soluble with?

Acrolein

Uses:

● In the production of acrylic acid

● As a chemical intermediate

● As a pesticide and herbicide

● In the manufacture of various chemicals

Acrylic Acid

Acrolein is used in the production of?

Acrylic Acid

A key ingredient in making plastics

Acrolein

Health impact: Toxic and irritating to the respiratory system, eyes, and skin

Acrolein

Environmental impact: Can contribute to air pollution when released into the atmosphere

Air Pollution

Acrolein can contribute to this when released into the athmosphere

Citral

Chemical Name: 3,7-dimethyl-2,6-octadienal

C10H16O

Molecular Formula of Citral

Citral

Structure: Contains an aldehyde group and two double bonds in an 8-carbon chain

Geranial (Citral A), and Neral (Citral B)

Isomers of Citral

Strong lemon

Scent of Geranial (Citral A)

Softer, sweeter lemon

Scent of Neral (Citral B)

Pale Yellow Liquid

Appearance of Citral

Strong lemon-like

Odor of Citral (Generally)

Lemongrass, Citrus Peels, Lemon Myrtle, and Orange Rind

Citral is found in essential oils like?

Citral

Used in:

● Perfumes and fragrances

● Flavoring agents (citrus flavors)

● Making Vitamin A and ionone compounds

Vitamin A, and Ionone

Citral is for making these compounds

Citral

Reactivity: Can undergo oxidation, reduction, and addition reactions (due to aldehyde and double bonds)

Oxidation, Reduction, and Addition Reactions

Citral can undergo these reactions due to aldehyde and double bonds

Methanal

Formaldehyde is also known as?

CH2O

Molecular Formula of Formaldehyde

Formaldehyde

H–C(=O)–H (the simplest aldehyde)

Aldehyde

Functional Group/s in Formaldehyde

Formalin

Formaldehyde is colorless gas at room temperature, often stored as a 37% aqueous solution called?

37% Aqueous Solution

Formaldehyde is stored as?

Strong, Pungent

Odor of Formaldehyde

Formaldehyde

Highly reactive due to small size and carbonyl group

Formaldehyde

Uses:

• Disinfectants and preservatives (especially in biological specimens)

• Manufacturing plastics and resins (e.g., Bakelite)

• Tissue fixation in labs

Formaldehyde

Toxicity: Highly toxic and carcinogenic with prolonged exposure

Very Soluble

Solubility of Formaldehyde to Water

Protocatechualdehyde

Chemical Name: 3,4-dihydroxybenzaldehyde

C7H6O3

Molecular Formula of Protocatechualdehyde

Protocatechualdehyde

A benzene ring with:

• Two hydroxyl groups (–OH) at positions 3 and 4

• One aldehyde group (–CHO) at position 1

Protocatechualdehyde

This compound is often studied in medical and pharmaceutical research because of its natural origin and useful properties.

Protocatechualdehyde

In short this is a bioactive plant compound with a helpful mixed of phenol and aldehyde chemistry

3, and 4

Protocatechualdehyde has two hydroxyl groups (-OH) at positions?

1

Protocatechualdehyde has one aldehyde group (-CHO) at position?

Phenol, and Aldehyde

Functional Group/s in Protocatechualdehyde

Yellow to Brown Crystalline Solid

Appearance of Protocatechualdehyde

Slightly Soluble

Solubility of Protocatechualdehyde to Water

Soluble

Solubility of Protocatechualdehyde to Alcohol, and Ether

Protocatechualdehyde

Natural Occurrence: Found in plants, especially in certain medicinal herbs and in coffee

Medicinal Herbs, and Coffee

Protocatechualdehyde is found in plants, especially in?

Protocatechualdehyde

Biological Activity:

• Antioxidant

• Anti-inflammatory

• Antimicrobial

Cinnamaldehyde

Chemical Name: 3-phenyl-2-propenal

C9H8O

Molecular Formula of Cinnamaldehyde

Cinnamaldehyde

Structure:

• A benzene ring attached to a 3-carbon chain with a double bond and a terminal aldehyde group

• Formula: C₆H₅–CH=CH–CHO

Cinnamaldehyde

Studied for its ANTIMICROBIAL PROPERTIES that can be used in medicine and preservation

Aromatic Ring (Benzene), Alkene, and Aldehyde

Functional Group/s in Cinnamaldehyde

Yellowish Oily Liquid

Appearance of Cinnamaldehyde

Sweet, spicy cinnamon-like

Odor of Cinnamaldehyde

Cinnamon Bark Oil

Cinnamaldehyde is main component of?