DAT Organic Chem

amphiprotic

molecule that can act as either acid or base

higher pH

more basic, more -OH

lower pH

more acidic, more H+

pKa and Ka values

increase Ka = decrease pKa

low pKa = high acidity = low pH

Rank Acids and Bases with CARDIO

Charge: more positive charge, more acidic. more negative charge, more basic

Atom: acidity increases from left to right across row (EN), and doing down the columns (atom size)

Resonance: increases stability of charge

Dipole Induction: electrons sucked away by withdrawal group makes it easier for H+ to leave (increase acidity), donating groups push electrons (decrease acidity)

Orbitals: more s-orbitals an atom has, more EN, more acidic. sp orbitals from triple bonds make the H more acidic than sp³ orbitals from single bonds

pH and Amino Acids

have carboxylic acid and amine group

pKa < pH = depronated molecule (missing H+)

pKa > pH = pronated molecule (filled with H+)

lower pH = more pronated

Configurational Isomers

Z vs E

cis vs trans

conformational isomers

Newman projections

anti-staggered, eclipsed, gauche staggered, total eclipsed

Naming Alcohols

1) parent chain is longest chain with -OH group

2) add -ol to end of parent chain

Naming Ethers

1) parent chain is whichever is the longer side on the O

2) name substituent on other side and add - oxy

Naming Amines

primary amine: add the suffix -amine to the parent chain

symmetrical amine: add di- or tri- to alkyl group

asymmetrical secondary or tertiary amine: the longer side is the parent group, add -amine, name substituents with prefix N-

naming aldehydes

1) parent chain is longest group that has the carbon with the double bond to O

2) replace -e with -al

naming ketones

1) name the parent chain replace -e with -one

2) number which carbon the double bond to O is

Naming Carboxylic Acids

1) parent chain is longest containing carboxylic acid

2) replace -e with -oic acid

Naming Acid Halides

1) replace -e with -oyl “name of halide”

4-methylpentanoyl iodide

naming esters

1) alkyl group atatched to single bonded O is listed first with suffix -yl

2) parent chain follows counting away from double bonded O, replace -e with -oate

ethylbutanoate

Naming Amides

1) group attached to nitrogen gets prefix N-

2) parent chain attached to double-bonded O replace -e with -amide

N-propyl butanamide

Naming Acid anhydrides

1) list both sides in alphabetical order, replace -e with -oic

2) add anhydride at end

butanoic propanoic anhydride

Naming Nitriles

add suffix -nitrile

pentanenitrile

Naming aromatics

1) give lowest number to highest priority group

2) use common name for the benzene and then add other substituents

1-chloro-2-methyl benzene or 2chlorotoluane

Naming spiro alkanes

spiro [a,b] parent name

parent name: total number of carbon atoms

a,b: number of carbons to the left and right of the center carbon: list lowest to highest

Bicyclic Alkanes

bicyclo [a,b,c] parent name

parent name: total number of electrons

a,b,c: number of carbons to the left, right, and above the center carbon: list highest to lowest

constitutional isomers

same chemical formula but different connectivity and location of atoms

enantiomers

mirror image

diastereomers

Non-mirror images

1) cis/trans isomers of ringed compounds

2) cis/trans or E/Z isomers of alkenes

3) molecules with multiple stereocenters that do not have exact opposite R/S forms

chiral centers

R: clockwise

S: counterclockwise

counting stereoisomers

2ⁿ

chirality (optical activity)

uses polarimeter to rotate plane-polarized light

L molecules: clockwise

D molecules: counterclockwise

physical properties of enantiomers

are the same and cannot tell apart

meso compounds

two or more stereocenters with a line of symmetry

dirrections cancel each other out to become achiral

fischer projections