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chem 22 > organic > Flashcards

organic Flashcards

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1
Q

hydrocarbon

A

organic compound that contains only carbon & hydrogen

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2
Q

saturated molecule

A

molecule that contains only C-C bonds

(substitution reactions)

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3
Q

unsaturated molecule

A

molecule that contains C=C or C≡C bonds

(addition reactions)

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4
Q

structural isomerism

A

molecules with identical molecular formulae, but different atomic structures

i.e. chain & positional isomers

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5
Q

geometric isomerism (stereoisomerism)

A

molecules with identical molecular formulae, but different spatial arrangements of atoms

i.e. when both carbons in a C=C bond (alkene) are attached to two different groups

cis-isomer : vertical symmetry

trans-isomer : vertical asymmetry

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6
Q

relationship between mass & dispersion forces

A

↑mass = ↑electrons = ↑dispersion forces

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7
Q

relationship between carbon chain length & dispersion forces

A

↑length = ↑surface area = ↑dispersion forces

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8
Q

even-numbered vs odd-numbered carbon chains

A

even-numbered carbon chains pack more tightly than odd-numbered carbon chains

∴ stronger dispersion forces

∴ greater boiling/melting point

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9
Q

straight vs branched carbon chains

A

straight carbon chains pack more tightly than branched carbon chains

∴ stronger dispersion forces

∴ greater boiling/melting point

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10
Q

markovnikov’s rule

A

when alkenes undergo addition reactions with H₂O or hydrogen halides, hydrogen joins the carbon of the C=C bond with more hydrogen (major product)

small proportion of products may oppose this rule (minor product)

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11
Q

primary, secondary & tertiary alcohols

A

primary : OH attached to a carbon with at least two hydrogen

secondary : OH attached to a carbon with one hydrogen

tertiary : OH attached to a carbon with no hydrogen

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12
Q

relationship between carbon chain length & hydrogen bonding

A

↑length = ↓hydrogen bonding attraction

∵ ↑overall non-polar nature

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13
Q

relationship between alcohol type & physical properties

A

boiling point : primary > secondary > tertiary

solubility : tertiary > secondary > primary

∵ branching - OH becomes less accessible to form hydrogen bonds

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14
Q

relationship between chain length & alcohol solubility

A

↑length = ↓solubility

∵ non-polar hydrocarbon chain becomes stronger

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15
Q

why are carboxylic acids more acidic than alcohols ?

A

hydrogen atom is more exposed

∴ greater ability to donate a proton (↑Kₐ )

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16
Q

intermolecular forces of carboxylic acids

A

two molecules of carboxylic acid can form a dimer connected by two hydrogen bonds

∴ stronger hydrogen bonding

∴ stronger dispersion forces (doubled mass)

17
Q

why are carboxylic acids more soluble than alcohols ?

A

COOH is more hydrophilic than OH

∵ both CO & OH can hydrogen bond with H₂O

18
Q

intermolecular forces of haloalkanes

A

dispersion forces & dipole-dipole attractions

∵ C-halogen bonds have high differences in electronegativity

19
Q

aldehydes

A

C=O in a terminal position

20
Q

ketones

A

C=O in a non-terminal position

21
Q

intermolecular forces of aldehydes & ketones

A

dispersion forces & dipole-dipole attractions

∵ ↑electronegative oxygen (polar C=O bond)

22
Q

intermolecular forces of esters (COO)

A

dispersion forces & dipole-dipole attractions

esters can accept hydrogen bonds from H₂O, but itself cannot hydrogen bond with H₂O

∵ no hydrogen atom

∴ slightly soluble from polarity, but less soluble than carboxylic acids

23
Q

basicity of amines

A

amines accept H⁺ if reacted in solution (brønsted-lowry base)

e.g. ethylamine + H⁺ → ethylammonium ion

24
Q

intermolecular forces of amines

A

dispersion forces & hydrogen bonding

highly polar amino group capable of forming multiple hydrogen bonds

∴ high boiling point

∴ high solubility

25
Q

functional group priorities

A

carboxyl > ester > amide > nitrile > carbonyl (aldehyde) > carbonyl (ketone) > hydroxyl > amino > alkene > alkyne > halo

26
Q

alkane reactivity

A

unreactive

∵ strong sigma bond

substitution reactions with halogens (UV) to form haloalkanes

combustion reactions with O₂ to produce CO₂, H₂O & heat

27
Q

alkene reactivity

A

↑reactivity than alkanes

∵ weak pi bond

reduction reactions with H₂ (Ni/heat) to form alkanes

addition reactions with H₂O (H₃PO₄/heat) to form alcohols

addition reactions with halogens (e.g. Br₂) to form dihaloalkanes

addition reactions with hydrogen halides (e.g. HBr) to form haloalkanes

28
Q

addition polymerization

A

monomers undergo addition reactions (catalyst/heat) to form polymers

e.g. ethene → polyethene

29
Q

combustion of alcohols

A

alcohol + O₂ → CO₂ + H₂O + energy

30
Q

oxidation of alcohols

A

oxidation reactions with K₂Cr₂O₇/KMnO₄ (H⁺/heat) to form :

primary : aldehyde

secondary : ketone

tertiary : inert (no replaceable hydrogen)

31
Q

esterification of alcohols

A

alcohol + carboxylic acid → ester + H₂O

(H₂SO₄)

e. g. methanol + propanoic acid → methyl propanoate + H₂O
- - -

hydrolysis : opposite of condensation

ester + H₂O → alcohol + carboxylic acid

(dilute H₂SO₄/heat)

32
Q

haloalkane reactivity

A

elimination reactions with NaOH (heat) to form alkenes

substitution reactions with NaOH to form alcohols

substitution reactions with KCN (ethanol/heat) to form nitriles (C≡N)

substitution reactions with NH₃ to form amines (NH₂)

substitution reactions with halogens to form dihaloalkanes

33
Q

aldehyde & ketone reactivity

A

aldehyde :

oxidation reactions with K₂Cr₂O₇/KMnO₄ (H⁺/heat) to form carboxylic acids

∵ terminal C=O (replaceable hydrogen)

ketones cannot oxidize

∵ non-terminal C=O (no replaceable hydrogen)

34
Q

nitrile reactivity

A

reduction reactions with H₂ (Ni/heat) to form amines (NH₂)

e.g. ethanenitrile + H₂ → ethanamine

35
Q

amine reactivity

A

condensation reactions with carboxylic acids to form amides (CONH₂)

e.g. methanamine + ethanoic acid → methylethanamide + H₂O

36
Q

bromine water test

A

alkene : brown → colorless

alkane : brown → brown

37
Q

acidified potassium dichromate test

A

1° & 2° alcohol : orange → green

3° alcohol : orange → orange

38
Q

acidified potassium permanganate

A

1° & 2° alcohol : purple → colorless

3° alcohol : purple → purple

chem 22 (7 decks)

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