PHA615 LAB: Classification Test for HC, Organic Halides, and Amines

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97 Terms

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Solublity in H2SO4

tests for alkenes

positive: reacts with alkenes thru Ae rxn

negative: all HC

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Ignition Test

more soot = aromatic

less soot = aliphatic

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Baeyer’s Test

does not colorized/brown ppt = active saturation

no rxn = alkanes, aromatic

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Baeyer’s Test

uses 2% KMnO4

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Bromine Test

orange-brown = alkene/alkyne (due to Ae)

no rxn = alkane/aromatic

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Bromine Test

Br2 in CCl4

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Iodine Test

I2 solution

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Iodine Test

tan-colored solid; to confirm presence of alkene/alkyne

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Nitration Test

yellow oily layer = aromatic

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Nitration Test

H2SO4 and HNO3

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Basic oxidation

decolorized = alkenes and alkyl side chain

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Basic oxidation

2% KMnO4

10% NaOH

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Beilstein/Copper Halide Test

green flame test = presence of halide

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Rxn with Ethanolic AgNO3

classifies type of RX

faster in tertiary RX

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Rxn with NaI in Acetone

classifies type of RX

faster in primary RX

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Rxn with Ethanolic AgNO3

2% alcoholic AgNO3

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Rxn with NaI in Acetone

15% NaI in anhydrous acetone

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Hinsberg Test

tests for type of amine
1 - soluble

2- insoluble

3- no rxn

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Hinsberg Test

10% NaOH and benzene sulfonyl Cl

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Solubility w/ HCl and NaOH

HCl + Amine = Soluble

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Solubility w/ HCl and NaOH

NaOH + Amine = insoluble

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Hydrocarbons

is a one of the two general classifications of organic compounds. These compounds are composed entirely of C and H atoms that are arranged and bonded in specific ways.

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Hydroxy

ROH and ArOH

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Mercapto

thiol and sulfides

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Amino

for amines

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Amido

amindes

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Halo

organic halides

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Carbonyl

aldehydes and ketones

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Carboxyl

carboxylic acid and derivatives

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Branching

decreases HC length making the HC more compact and dense.

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The # of carbon atoms

increases hydrophobicity = less polar.

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H-bonding

-C=O, -COOH, -OH, -NH2

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Dipole-Dipole

OH, -NH2, -X, -SH, -C=O, -COOH

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London Dispersion / Hydrophobic

HC

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Aromaticity

is based on distinct characteristics present in a hydrocarbon as well as its conformance to the Huckel’s rule.

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Aromatic

is a hydrocarbon that contains one or more benzenelike rings and can be described as: • Cyclic • Planar • Possess conjugated double bonds (ex. C=C—C=C) • Possess 4n+2 π electrons (Huckel’s rule).

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HC

are generally soluble in organic solvent / insoluble in water.

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Solubility

is inversely related to melting point (↑ MP = ↓ solubility)

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Combustibility

is a measure of how easily a substance bursts into flame through fire or combustion

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Flammability

is the ease with which a combustible substance can be ignited causing fire, combustion, or even explosion.

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Test of Unsaturation

It can be used to determine the presence of a double/triple bond (unsaturation) in a compound.

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Test of Unsaturation

It can differentiate active unsaturation from aromatic compounds.

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Test of Unsaturation

Baeyer’s test, Bromine test, and Iodine test

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Baeyer’s test

uses KMnO4 and is a form of oxidation reaction which forms a brown suspension/sludge. It detects the presence of active unsaturation like in alkenes and alkynes

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Bromine test

uses Br2 in CCl4 to confirm the presence of double/triple bonds. It is an addition reaction in which the Br2 solution is decolorized when mixed with unsaturated compounds.

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Iodine test

uses I2 solution and is also an addition reaction used to confirm the presence of alkene/alkynes. The positive result for this test is the formation of a tan-colored solid while retaining the color of the I2 solution.

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Nitration Test

is a common substitution reaction for aromatic molecules. It is used to detect the presence of benzene rings in a compound.

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Nitration Test

The formation of a yellow oily layer confirms the presence of a benzene ring.

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Basic Oxidation

This test uses KMnO4 in NaOH solution and is often referred to as mild oxidation.

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Basic Oxidation

It can be used to detect the presence of alkene and benzylic carbon (must have benzylic hydrogen) that are both susceptible to oxidation.

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Basic Oxidation

A brown precipitation or suspension confirm the presence of the target organic compounds.

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Organic halides

or haloalkanes (RX) are organic compounds that contains a halogen moiety (-X = F, Cl, Br, and I).

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RX

is soluble in organic solvent but are insoluble in water despite being polar.

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RX

can exhibit dipole-dipole interactions because of the C-X bond where the polarity is shifted -X causing it to be polar.

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RX

reacts via substitution and elimination reactions.

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decreases

The bond strength of C-X _ as the size of the halogen increases. Iodine is a better leaving group during reactions compared to fluorine.

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Beilstein Test

This is a flame test that detects the presence of halogens from samples.

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Beilstein Test

It uses CuO that reacts with the halogen forming copper-halide compounds which is visible via the formation of blue-green flame.

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SN1

  • unimolecular; reaction is dependent only on the RX

    • Tertiary RX with “stable” carbocation formed from their alpha carbons uses this mechanism.

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SN2

bimolecular; reaction is dependent on the RX and the Nü. • This mechanism is common for primary and secondary RX.

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SN1

Reaction with Alcoholic AgNO3. • The Ag in AgNO3 acts as a Lewis acid and promotes the formation of the carbocation. AgX is formed as a by-product together with the R+ .

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SN2

Reaction with NaI in Acetone • The I- in NaI in acetone displaces the X in not sterically hindered RX (primary or secondary RX) resulting in R-I (alkyl iodide) and a NaX (Br or Cl) salt. • NaI is soluble in acetone but NaBr/NaCl are not and will form a precipitate indicating the occurrence of an SN2 reaction.

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Amines

are nitrogen-containing organic compounds which can be classified as primary, secondary, or tertiary based on the number of alkyl (R-) groups attached to the nitrogen atom.

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RNH2

are basic and have a characteristic fishy odor and can exist as liquids (low carbon) or solids (higher carbon) depending on the number of carbons.

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hydrogen bonding

The presence of H atoms results into _ which cause higher boiling for primary amines (BP primary > secondary > tertiary).

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Amines

_ are soluble in water due to its ability to undergo H-bonding. However, as the size of the alkyl group increases, water solubility decreases.

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Aromatic

_ amines (ex. Aniline) readily undergoes atmospheric oxidation can gets colored as a result

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Hinsberg Test

This uses benzene sulfonyl chloride to differentiate between primary, secondary, and tertiary amines

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soluble

Primary amines forms alkali _ sulfonamide product.

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insoluble

Secondary amines forms alkali _ sulfonamide product.

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do not

Tertiary amines _ react.

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blue-green

A _colored flame indicates the presence of Br, Cl, & I

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Solubility with HCl and NaOH

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Hinsberg Test

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Reaction with NaI in Acetone

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Reaction with Ethanolic AgNO3

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Beilstein Test or Copper Halide Test

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Basic Oxidation Test

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Nitration Test

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Baeyer’s test

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Ignition Test

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Solubility in H2SO4

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Ignition Test

It can be used to classify aliphatic from aromatic hydrocarbons.

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Aliphatic

HC burns with yellow flame that are less sooty

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Aromatic

HC burns with yellow flame that are more soot

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active unsaturation

A (+) decolorized result and (+) brown suspension/sludge in Baeyer’s test, confirms the presence of _ in cyclohexene.

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Baeyer’s Test

KMnO4 with alkenes produces a vicinal diol or glycol. This is mild oxidation reaction.

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Baeyer’s Test

KMnO4 does not affect alkanes (unreactive) and aromatic compounds (too stable, inactive unsaturation).

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Bromine Test

will start as orange-brownish solution and will decolorize if the test is positive for the presence of alkenes or alkynes. • Br2 can undergo AE reaction mechanism to add itself to the double or triple bond. • Br2 can mix with aromatic compound in the presence of the appropriate catalysts, but will not react with alkanes upon mixing.

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Nitration Test

The reaction occurs via SE mechanism which is specific for aromatic compounds. The nitrating mixture composed of H2SO4 and HNO3 creates the electrophile -NO2+ .

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Basic Oxidation

Alkenes are able to undergo mild oxidation with KMnO4 resulting to a decolorized solution (similar to Baeyer’s test).

Alkyl side-chain on a benzene ring (benzylic position) is fairly resistant to oxidation but in an alkaline solution with KMnO4, the benyzlic hydrogen is easily oxidized into a -COOH moiety.

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Chlorobenzene

_ did not react to either SN1 or SN2 because it is an aromatic halides.

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SN1

Alkyl halide (RX) - faster reaction is observed with more stable carbocation. • Solvent - any polar solvent that increases the stability of the carbocation will also speed up the reaction rate. • Leaving group - best leaving groups are those that can stabilize the anion (eg., weakest bases).

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SN2

Steric congestion - the more steric present, the slower the reaction. • Solvent - exposing the Nü to a more polar solvate = more reactive iodide. • Nucleophile - atoms from same family in periodic table, the larger members of the family are better Nü. • Leaving group - best leaving groups are those that can stabilize the anion (eg., weakest bases).

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Hinsberg test

will differentiate primary, secondary, and tertiary amines based on the products they form.

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HCl

In _ solutions, amine are soluble due to the ability to form H-bonding with the -Cl moiety. Amines + _ is a form of a neutralization reaction.

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NaOH

In _ solutions, amines are insoluble due to lack of intermolecular attraction (amine only have weak H-bonding and dipole-dipole) to break the ionic bond within NaOH and the presence of hydrophobic moieties.