Content OC Flashcards by Roxana Boff

electron domain: 4

geometry: linear
bond angle: 180
hybrid.: sp

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electron domain: 3

geometry: trigonal planar
bond angle: 120
hybrid.: sp2

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electron domain: 2

geometry: tetrahedral
bond angle: 109.5
hybrid.: sp3

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single bond

one sigma

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double bond

one sigma
one pi

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triple bond

one sigma
two pi

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determining greatest resonance contributer

the most stable will have a full octet on every atom

the most stable will have the smallest number of charges

the most stable will have neg. charges on the most electroneg. atoms and positive charge on the least electroneg. atoms

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order of stability in newman projections

staggered > gauche > eclipsed axi

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axial vs equatorial

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equatorial bonds are more ________

stable ( lower energy ) than axial

place largest sub on equatorial to get greatest stability

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cis

two subs. in the same direction

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trans

two subs. in opposite direction

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a lewis acid ______ electrons

accepts

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a lewis base _______ electrons

donates

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the stronger the acid, ______

the weaker/ more stable the conjugate base

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the stronger the base, ________

the more stable/weaker the conjugate acid

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pks for organic compounds

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the more positively charged,

the more acidic

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the more negatively charged,

the more basic

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if all factors are about the same, then hydrogens acidity increases as the atom that it’s bonded to:

goes left to right across a row
goes down a column

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electron withdrawing groups increase

acidity

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electron donating groups decrease

acidity

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s-orbitals tend to be more electroneg., so the more “s” character :

the stronger the acid

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C
A
R
D
I
O

Charge: positively charged compounds are typically more acidic, negatively charged compounds are more basic

Atom: the more electroneg./ larger the atom with a negative charge, the more acidic the hydrogen is

Resonance: the more resonance stabilized the conjugate base, the stronger the acid

Dipole Induction: electron withdrawing groups increase acidity, electron donating groups decrease acidity

Orbitals: the more s-character an atom has, the more electroneg it is, and the more acidic hydrogens bonded to it will be sp3<sp2< sp

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as KA increases, pka ____, and acid strength ______

decreases increases

if the pH of the solution is lower than the pKa of the functional group,

the functional group will be protonated

if the pH of the solution is higher than the pKa of the functional group,

the functional group will be deprotonated

amino acid if protonated ( pH < pKa )

- NH3 +

amino acid if deprotonated ( pH > pKa )

-NH2

carboxylic acid group if protonated ( pH < pKa )

- COOH

carboxylic acid group if deprotonated ( pH > pKa )

- COO-

hydroxyl group if protonated ( pka > pH )

-OH

hydroxyl group if deprotonated ( pH > pKa)

-O-

when counting how many steroisomers one chiral molecule can have, use the equation:

2^n n is the number of chiral centers

chiral molecules have the ability to

rotate olan polarized light when placed in a special machine called a polarimeter

Molecules that do not rotate plane-polarized light are called

achiral or inactive

there are 3 types of optically inactive ( or achiral ) molecules:

1. 50/50 racemic mixture of two enantiomers ( racemic mixture ) 2. molecules that do not have stereochemistry in the them 3. meso compounds

meso compound

any molecule with 2 or more chirality centers, and a line of symmetry an enantiomer of a meso compound is exactly the same as the original molecule ( 2 are superimposable )

fisher projection

look up pls

a BIG point peak at 1700+/- 50 cm-1

C=O

a LARGE, broad trough far to the left for alcohols and on top of 3000 cm-1 for carboxylic acids

big, pointy peaks coming straight down around 3000 cm-1

C-H's

a sharp peak to the left of 3000 ( around 3200-3500)

N-H (one peak for -NH, two peaks for -NH2)

medium sized peak at -2200

C (tripled bond) N - a nitrile

vampire teeth at 1500-1600 and 1300-1400

NO2

carbon-carbon double bonds are found in which IR region?

1600 cm-1

carbon-nitrogen double bonds (imines) are found in which IR region?

1600 cm-1

UV-Vis spectroscopy

is used mostly to analyze compounds with conjugated double bonds

mass spectroscopy

technique used to determine a compounds mass

degree of unsaturation

(A-B) /2 a is the number of hydrogen atoms your compound would have if it didnt have any double bonds or rings b is the number of hydrogen atoms your compound in question actually has

degree of unsaturation

c- (h/2) - (x/2)+ (n/2) +1

more negatively charged a carbon

further down to the right of 13C-NMR spectroscopy

more positively charged a carbon

further down to the left of 13C-NMR

Carbonyl carbons - esters, amides, and carboxylic acids - aldehydes and ketones Kind of C-NMR?

160 - 180 ppm > 200 ppm

TMS (tetramethysilane) Kind of C-NMR?

0 ppm not part of your compound?

1 H - NMR spectroscopy carboxylic acid and amide H's

12,13,14

1 H - NMR spectroscopy phenols and aldehydes

1 H - NMR spectroscopy aromatic land ( H's stuck to benzene)

6,7,8

1 H - NMR spectroscopy double bonds land

4,5,6

1 H - NMR spectroscopy single bond land

1,2,3,4,5

1 H - NMR spectroscopy Alcohol and amine H's

0.5-5.5 ppm

1 H - NMR spectroscopy TMS

0 not apart of your compound!

1 H - NMR spectroscopy the more + charged =

more left, downfield

hydrogens get split by neighboring hydrogens. To figure out splitting,

count all the hydrogens next door in all directions and add (n+1 rule)

Intra-molecular Forces (within) Covalent

two non metals atoms bond together and share electrons

Intra-molecular Forces (within) Ionic bonds

metal bond to nonmetals and a transfer of electrons occurs

Intra-molecular Forces (within) metallic bonds

metal atoms bond together and electrons flow freely around their nuclei

Inter- molecular Forces ( between molecules ) ion dipole

ionic compounds interacting with polar compounds

Inter- molecular Forces ( between molecules ) hydrogen bonding

H-O H- N H-F

Inter- molecular Forces ( between molecules ) dipole dipole

H-Cl C-O S-H

Inter- molecular Forces ( between molecules ) dispersion forces

hydrocarbons single elements non polar molecules

tollens test

reagent: Ag,O/NH3 or Ag(NH3)2 function group tested: aldehydes positive result: sides of flask are coated with a silver mirror

iodoform test

reagent: I2/OH functional group tested: methyl ketones positive result: yellow percipitate forms (CHI3)

silver nitrate in alcohol

reagent: AgNO3 in alcohol function group tested: alkyl halide s positive result: precipitate of Ag compound formed

bromine test

reagent: Br2/CCl4 Functional group tested: alkenes and alkynes positive result: brown color of bromine disappears

baeyer test

reagent: dilute KMnO4 functional groups tested: alkenes and alkynes positive result: purple solution turns to brown precipitate

Jones Test

reagent: CrO3 / H2SO4 functional groups tested: 1 and 2 alcohols positive result: orange reagent turns blue-green

Lucas Test

reagent: ZnCl2/HCl Functional groups being tested: 2,3 and benzylic alcohols positive results: cloudy solution initially, then separate layer forms

metallic

Interaction: Metallic Bonding Properties: Variable hardness and melting point, conductive Examples: Fe, Mg

Ionic

Interaction: Ionic Properties: High melting point, brittle, hard Examples: NaCl, MgO

Network

Interaction: Covalent Network Properties: High melting point, hard, non conductive Examples: C (diamond, graphite) SiO2 (quartz)

Molecular

Interactions: H Bonding, dipole dipole, London dispersion Properties: Low melting point, non conductive Examples: H2, CO2

the stronger a molecules intermolecular forces:

higher the BP higher its MP lower its VP

melting points help determine a compounds

purity

for carboxylic acids, extract with

NaOH or NaHCO3

for phenols, extract with

NaOH

for amines, extract with

aqueous HCl

separates mixtures of 2 or more volatile liquids

distillation

used when 2 volatile liquids have boiling points that are closer together

fractional distillation

dissolves an impure compound in hot solvent and gradually precipitates the pure compound as the solution cools down

recrystallization

glass liquid chromatography

used to determine the relative abundance of each compound in a liquid mixture separates components in liquid mixture by boiling point lowest boiling point comes off the fastest

thin layer chromatography

separates compounds by their solubility in the solvent (polarity) most soluble compound travels the fastest and furthest up the plate usually uses polar plates and non polar solvent compound that travels the furthest with non polar solvent is the most non polar compound retention factor (Rf) is the number we use to tell how far up the TLC plate a compound travels

Content OC Flashcards

(92 cards)