ORGMED LAB ACT 1

ALKANES

CnH2n+2 

Aliphatic compounds 

Saturated hydrocarbons 

Carbon–carbon single bonds (C-C)

insoluble

Alkanes and cycloalkanes are_______in water. 

increase in carbon–chain length or ring size

The boiling points of continuous chain alkanes and cycloalkanes increase with an_______________. 

5 to 17 carbon atoms

Continuous-chain alkanes containing________are liquids.

17 carbon atoms

Alkanes that have_______are solids at room temperature

COMBUSTION

Chemical reaction between a substance and oxygen (usually from air) that proceeds with the evolution of heat and light (usually as a flame).

Oxidation reaction

HALOGENATION

Chemical reaction between a substance and a halogen in which one or more halogen atoms are incorporated into molecules of the substance.

ALKENES

CnH2n

an acyclic unsaturated hydrocarbon that contains one or more carbon– carbon double bonds. 

has fewer hydrogen atoms than alkane.

olefins

alkenes are also called as?

ALKYNES

CnH2n-2

Carbon with multiple bond 

carbon–carbon triple bonds (C≡C) 

acyclic unsaturated hydrocarbon that contains one or more carbon–carbon triple bonds. 

insoluble in water , less than that of water , with molecular mas

Alkynes are_________but soluble in organic solvents, have densities________, and have boiling points that increases______. 

- triple bonds move , - carbon chains move

Constitutional isomers are possible for alkynes, in Positional isomers the while in Skeletal isomer the________.

ADDITION REACTION

chemical reaction in which atoms or groups of atoms are added to each carbon atom of a carbon–carbon multiple bonds in a hydrocarbon or hydrocarbon derivative

Alkene, Alkane

product of addition reaction?

 HYDROGENATION

addition reaction in which hydrogen atoms are incorporated into molecules of an organic compound. 

presence of a catalyst (usually Ni or Pt). 

To speed up chemical reaction

HALOGENATION

addition reaction in which two halogen atoms are incorporated into molecules of an organic compound. 

no catalyst is needed.

chlorination and bromination.

Usually halogenation occurs in_______.

HYDROHALOGENATION

addition reaction in which a hydrogen halide (hydrogen + halogen=HCl, HBr, or HI) is incorporated into molecules of an organic compound.

No catalyst is needed.

One carbon atom receives halogen and the other carbon atom receives hydrogen.

 HYDRATION REACTION

addition reaction in which H2O is incorporated into molecules of an organic compound 

Completely miscible with water

Unsubstituted C1 to C4 monocarboxylic acids are?

1.) water soluble

2.) not water soluble

Short-chain dicarboxylic acids are also________.

Aromatic acids are___________________.

liquids that have strong, sharp odors

Unsubstituted saturated monocarboxylic acid containing up to nine carbon atoms are?

are waxy solids that are odorless

carboxylic acids that have 10 or more carbon atoms in an unbranched chain are?

nitriles

Carboxylic acids can be prepared from_________on heating with aqueous acid or base

SN2 reaction

Nitriles are made by_______ of a primary or secondary alkyl halide with CN2

metal carboxylate,

The reaction of a Grignard reagent with CO2 yields a_____________followed by protonation to give a carboxylic acid.

 DEPROTONATION

Oxygen takes the electron of hydrogen which breaks the bond of hydrogen to the carboxylic acid leaving a free lone pair of electrons.

 REDUCTION

 Alpha Substitution Reaction aka Hell-Volhard-Zelinsky (HVZ)

Carboxylic acid to Ketone.

Keto-Enol tautomerism.

Enol Tautomer reaction with Dihalide

Reaction with Water.

Hell-Volhard-Zelinsky reaction in for steps?

ESTERS

have lower boiling points than carboxylic acids, and they are also volatile

very insoluble in water

Large esters are____________ but soluble in organic solvents

Alcoholysis

When acid chloride is reacted with alcohol, its OR group of alcohol will displace Cl group since the OR group has higher affinity.

Then the chloride group will be cleaved and will bond to the remaining hydrogen in the alcohol. This will form an ester.

Fischer Esterification

So when benzoic acid is reacted with the OR group of ethanol, the OR group will displace the hydroxyl group of benzoic acid and replace it. And the hydroxyl group will bind to the hydrogen atom left of ethanol when the OR group leaves.

 HYDROLYSIS

• Conversion of Esters into Carboxylic Acids

In basic solution is called saponification

 REDUCTION

Conversion of Esters into Alcohols

AMINOLYSIS

• Conversion of Esters into Amides

• Esters react with ammonia and amines to yield amides 

GRIGNARD REACTION

Conversion of Esters into Alcohol

ALDEHYDES

an organic compound in which the carbonyl group is attached to a carbon atom at the end of a carbon chain.

The R group may be a hydrogen atom or any length carbon chain.

C3 to C11

aldehydes that has C1 and C2 are gasses at room temperature. ______saturated aldehydes are liquid at room temperature.

carbonyl oxygen atom.

Aldehydes can form weak hydrogen bonds with water through the_______.

have pleasant odors

Lower carbon atoms have pungent odors, while many higher aldehydes (C8 and above)_______.

FORMALDEHYDE (METHANAL)

Sold as formalin

Manufacture of Bakelite, a hard plastic with high chemical and electrical resistance.

ACETALDEHYDE (ETHANAL)

Widely found in nature

Fuel combustion emissions, immediate product of alcohol fermentation, and metabolism of sugar in the body.

PROPIONALDEHYDE OR PROPANAL

Clear colorless liquid 

Overpowering fruity-like odor 

Less dense than water 

Metabolite found in or produced by Escherichia coli (strain K12, MG1655)

KETONES

• have a carbonyl group (C=O) bonded to two carbon atoms.

• The carbonyl carbon has trigonal planar geometry.

• It forms sigma bonds with adjacent carbons and a pi bond with oxygen.

higher boiling points

Ketones have_______and are polar, making them soluble in water to a degree

carboxylic acids , secondary alcohols

Ketones can be oxidized to____________or reduced to____________.

ACETONE (Dimethyl ketone)

•  it is used in chemical peeling and for acne treatments. 

  • Note: The presence of ______ in urine is a sign of diabetes.

• In household, it is used as a major component of some nail polish removers and paint thinner

METHYL ETHYL KETONE

A colorless, flammable liquid with a sharp, sweet odor, soluble in water and alcohol 

Boils at a higher temperature and has a slower evaporation rate than acetone

CYCLOHEXANONE

A  clear, colorless to pale yellow liquid with a mint or Acetone-like odor

Less dense than water but its vapors are heavier than air 

Miscible in both ethanol and ether

antihistamines.

Cyclohexanone in pharmaceutical industry, its derivatives are used in the synthesis of?

adipic acid and caprolactam,

Cyclohexanone in nylon industry, its derivatives are oxidized to produce________precursors for nylon 6.

ALCOHOL

Organic compound with a hydroxyl (OH) functional group on an aliphatic carbon atom.

increase in the number of carbon atoms

The boiling point of alcohol increases with the____________, as stronger van der waals forces start acting in between the molecules.

 Primary Alcohol (RCH2OH) 

are those alcohols where the carbon atom of the hydroxyl group (OH) is attached to only one alkyl group.

Secondary Alcohol (R2CHOH) 

are those where the carbon atom of the hydroxyl group is attached to two alkyl groups on either side.

Tertiary Alcohol (R3COH) 

are those which feature a hydroxyl group attached to the carbon atom which is connected to 3- alkyl groups.

DEHYDRATION REACTION

The reaction removes the OH group from the alcohol carbon atom and a hydrogen atom from an adjacent carbon atom in the same molecule

Catalysts: 180 degrees Celsius & Sulfuric acid (H2SO4)

catalyst of dehydration reaction?

aldehydes and carboxylic acids

Primary alcohols can be oxidized to form

ketones.

Secondary alcohols can be oxidized to give

Oxidation of Alcohols

These are catalysts for what reaction?

Catalysts: Potassium dichromate (K₂Cr₂O₇), Chromic acid (H₂CrO₄), Chromium trioxide (CrO3)

good bases and nucleophile

sodium alkoxides are both

weak acids

___________ don’t protonate alcohols to any significant extent

ETHER

• Organic compound that consists of oxygen atom bonded to two aryl or alkyl groups.

• Two carbon atoms bonded to an oxygen

• alkanes.

• Boiling points of ethers are similar to those of?

Higher boiling point

Ether has__________of the alcohol.

unstable hydroperoxides and peroxides

Ethers react slowly with oxygen from the air to form____________.

SN1 mechanism

When using HBr or HI, the acidic cleavage of ethers with tertiary, benzylic, or allylic substituents tend to occur by an__________.

SN2 reaction

It is important to note that a phenyl substituent on an ether is not capable of participating in the______of an acidic cleavage.

false, alcohol is denser than ether

t or f

alcohol is less dense than ether?

APROTIC SOLVENTS

ETHER IS USED IN

AMIDE

 is an organic molecule with a functional group made up of an acyl group (R–C=O) linked to a nitrogen atom.

soluble

AMIDES are typically________in polar solvents like water due to their capacity to establish hydrogen bonds with water molecules

hydrolysis reactions

AMIDES can undergo______under acidic or basic conditions

Primary amide

 in which the only substituent on the amide’s nitrogen atom is hydrogen.

Secondary amide

In which the amide’s nitrogen atom is linked to a hydrocarbon substituent

Tertiary amide

 one in which the amide nitrogen atom is linked to three carbon atoms

FORMAMIDE

Simplest carboxylic acid amide

Formed by heating CO2 and NH3 under pressure

Uses: feedstock in manufacture of formate esters, ionizing solvent, and tissue preservation

ACETAMIDE

Acetic acid amide or Ethanamide

Simplest amide derived from acetic acid & naturally found in red beetroot

Uses: plasticizer, explosive, and penetrating agent 

BENZAMIDE

Simplest amide derivative of benzoic acid

Found in the herbs of Berberis pruinosa.

Uses: organic synthesis, manufacture of benzonitrile

AMINES

Organic derivative of ammonia (NH3) in which one or more alkyl, cycloalkyl or aryl groups have replaced ammonia hydrogen atoms

are liquids at room temperature

Primary amines with 3 OR 4 carbon atoms_____________.

soluble in water

Lower aliphatic amines are

ANILINE

• primary amine in which the nitrogen atom is attached directly to a benzene ring

BENZYLAMINE

primary amine compound having benzyl as the N-substituent

DOPAMINE

Drug of choice for Cardiogenic shock

• Parkinson’s disease

• ex: Sinemet

NOREPINEPHRINE

• Drug of choice for Septic shock

• Constricts blood vessels

• ex: Levophed

SEROTONIN

• Involved in sleep, sensory perception and regulation of body temperature

• Based on tryptamine core

EPINEPHRINE

Drug of choice for anaphylactic shock

•  Produced by adrenal glands from norepinephrine 

ARENES

• are a type of aromatic hydrocarbons. 

  • These are hydrocarbons with sigma bonds and delocalized pi electrons between carbon atoms forming rings. 

eight carbon atoms

• Arenes up to_____________are colourless liquids with characteristic odor.

• Arenes are insoluble in water

•  Fairly soluble in organic solvents

active pharmaceutical ingredients

arenes are used as________in new drug synthesis since the stability of the aromatic ring provides resistance against metabolic degradation

specific histamine receptors,

Arene block works by binding to________thereby preventing histamine from attaching to these receptors and triggering an allergic response

ELECTROPHILIC SUBSTITUTION REACTION

a chemical reaction in which the hydrogen atom attached to a compound is replaced by an electrophile.

EPOXIDES

• It is a cyclic ether that contains three atom rings.

• Exist as a colorless, non polar, and volatile compound.

ethylene oxide and propylene oxide

Some of the most common examples of epoxides are

Regioselectivity

bond forming in a specific location of a molecule

Alcoholysis

reaction where alcohol is the reactant which later on, becomes part of the reaction