ORG CHEM LAB - EXP #7-9

soluble

solubility of small molecules in H2O

soluble

solubility of small molecules in H2O

soluble

solubility of polar molecules in H2O

insoluble

solubility of non-polar molecules in H2O

soluble

solubility of ionic form in H2O

insoluble

solubility of neutral form in H2O

alkene functional group oxygen nitrogen

organic compound containing ________________ are soluble in concentrated H2SO4

alkanes (single bonds) alkyl halides some aromatic compounds (benzene, naphthalene, anthracene)

only _________________ are insoluble in H2SO4

IGNITION TEST

indicates the presence of unsaturation / high carbon to hydrogen ratio; assessed by the presence of yellow flame and soot

SOOTY FLAME; INCOMPLETE COMBUSTION

aromatic compounds burn with ______________ due to the ______________ which causes the formation of an unburned carbon

COMPLETE COMBUSTION

hydrogen/sample will interact with oxygen; produce CO2 and H2O

INCOMPLETE COMBUSTION

poor oxygen/air supply; produce CO (carbon monoxide), carbon - released as soot (black), water

ADOLF VON BAEYER

Baeyer's test is named after

2% KMnO4 (potassium permanganate)

reagent for Baeyer's test

discolorization of purple colored solution and formation of brown precipitate

positive result for Baeyer's test

O.5% Br in CCl4 reagent

reagent for Bromine test

discolorization of an orange-colored solution

positive result for Bromine test

NITRATION

test for aromaticity; detects presence of aromatic compounds

HNO3; H2SO4

reagents for nitration

Yellow oily layer

positive result for nitration

OXIDATION TEST

detects presence of alkylated aromatics

2% KMnO4

reagent for oxidation test

Color change in the solution (green solution) brown precipitate

positive result for oxidation test

ORGANIC HALIDES

halogens that bear a negative charge

α carbon

first carbon atom that is attached to a functional group

PRIMARY

one alkyl group is attached to α carbon

SECONDARY

two alkyl groups are attached to α carbon

TERTIARY

three alkyl groups are attached to α carbon

NUCLEOPHILIC SUBSTITUTION

fundamental class of reactions in which an electron-rich nucleophile selectively bonds with or attacks the positive or partially positive-charge of an atom / a group of atoms to replace a leaving group

NUCLEOPHILE

nucleus-loving / positive charge loving; contain a lone pair of electrons

LEAVING GROUP

atom/molecule that leaves / that is displaced as more stable species replace it in a chemical reaction

GOOD LEAVING GROUP

can be stable on its own; ex: chlorides, bromides, iodides

EXTREMELY POOR LEAVING GROUPS

have the ability to form strong bonds; ex: fluorides

SN1

if the rate of reaction is dependent on the organic halide/leaving group only (one factor) -- unimolecular

SN2

if the rate of reaction is dependent on both the organic halide and the nucleophile (two factors) -- bimolecular

BEILSTEIN TEST

detect presence of halides

Friedrich Konrad Beilstein

He developed the beilstein test

green flame (only for chloride, bromide, iodide)

positive result for beilstein test

CARBOCATIONS

positively charged carbon ions that are usually formed when alkyl halides react

SN1 REACTIVITY TEST: REACTION WITH AgNO3

positive results depend on the stability of carbocations

SN2 REACTIVITY: REACTION WITH NaI in Acetone

results depend on steric hindrance

SUGARS

contain both hydroxyl and carbonyl group

D-GLUCOSE

the most common type of glucose

DEXTROTATORY GLUCOSE; DEXTROSE; ALDOHEXOSE

another names for glucose

PRIMARY ALCOHOLS

are those alcohols where the α carbon atom is attached to only one single alkyl group

SECONDARY ALCOHOLS

are those where the α carbon atom is attached to two alkyl groups on either side

TERTIARY ALCOHOLS

are those which feature hydroxyl group attached to the α carbon atom which is connected to three alkyl groups

LIKE DISSOLVES LIKE

general rule for solubility

PRIMARY ALCOHOL

alcohol that is most soluble

TERTIARY ALCOHOL

alcohol that is least soluble

BENZENE RING

alcohol that is immiscible in water due to the presence of benzene ring

LUCAS TEST

detects the type of alcohol present; with a positive result of turbid, cloudy, and hazy one

LUCAS REAGENT

anhydrous zinc chloride in concentrated hydrochloric acid

SIR EWART JONES

chromic acid test was named after him

CHROMIC ACID TEST

detects presence of primary, secondary, aldehyde

JONES OXIDATION

another name for chromic acid test

JONES REAGENT

chromium trioxide in concentrated sulfuric acid

POTASSIUM DICHROMATE IN CONCENTRATED SULFURIC ACID

alternative for jones reagent

GREEN COLOR OF Cr3+

positive result in chromic acid test

2,4-DNP TEST

detects presence of aldehyde / ketone (detects presence of carbonyl group)

DINITROPHENYLHYDRAZINE

DNP in 2,4-DNP TEST

BRADY'S TEST

another name for 2,4-DNP test

BRADY'S REAGENT

2,4-dinitrophenylhydrazine in a mixture of methanol and concentrated sulfuric acid

FORMATION OF A YELLOW TO ORANGE-RED PRECIPITATE

positive result for brady's test

H.C. Von Fehling

a German chemist who developed the Fehling's test

FEHLING'S TEST

distinguish aldehyde/ketone (positive result; aldehyde)

COPPER (II) SULFATE

Fehling's A

POTASSIUM SODIUM TARTRATE (ROCHELLE SALT) & NaOH

Fehling's B

Blue

color of Fehling's A

Clear liquid

color of Fehling's B

FORMATION OF REDDISH-BROWN PRECIPITATE

positive result for Fehling's test

Bernhard Tollens

Tollen's reagent named after

TOLLEN'S SILVER MIRROR TEST

another test used to distinguish aldehyde/ketone (positive result=aldehyde--H atom oxidized; silver ion reduced)

TOLLEN'S REAGENT

solution of silver nitrate with NaOH and ammonium hydroxide

METALLIC SILVER (formed by reduction of silver ions) forming a SILVER MIRROR

positive result of Tollen's Silver Mirror Test