Kaplan MCAT OChem Ch. 1 Nomenclature

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straight-chain alkanes/alkanes

simplest of organic molecules

chain of carbons connected by single bonds w/ H atoms attached

C(n)H(2n+2)

ending in "-ane"

branched-chain alkanes

smaller carbon chains branching off main chain

substituents

suffix "-yl"

"n" = normal = sub is straight-chain alkane attached to backbone at one end of its chain

assume molecule is normal unless stated otherwise

multiple => di, tri, tetra (ignored in alpha)

name is alpha order (also iso, neo, cyclo)

separate numbers from number w/ commas; separate numbers from words w/ hyphens

cycloalkane

rings

C(n)H(2n) (like alkene)

degree of unsaturation - loss of hydrogens when C makes an additional bond (ex: two fewer -> 1)


ring numbered starting w/ carbon w/ most substituents

goal is give lowest series of numbers possible

more complicated molecules

when counting long chain, MUST have highest-priority functional group included, receiving lowest number and suffix of group

higher functional group compound just need to be more oxidized

alkenes

AKA olefins

end in "ene"

C(n)H(2n) (DOU)

if multiple DBs, chains contains greatest # of them

config isomer (cis/trans, E,Z)

alkenes as sub

vinyl- (ethenyl), allyl-, methylene-

vinyl-

monosub ethylenes (ethenyl)


http://0.tqn.com/d/chemistry/1/0/Y/o/Vinyl-chloride-2D.jpg

allyl-

propylenes attached to backbone at C-3 position

http://upload.wikimedia.org/wikipedia/commons/3/33/AllylBromide.png

methylene-

only one carbon DB to rest of molecule

http://upload.wikimedia.org/wikipedia/commons/1/1e/Methylenecyclohexane.png

cycloalkenes

if only one DB and no sub => no number needed

conjugated system

alternating single and DB

alkynes

suffix "yne"

# indicate position

always linear

common name: acetylene

C(n)H(2n-2)

two degree of unsat since has 2 pi bonds

when both DB and TB -< DB given lowest #

acetylene

common name of two triple bonded carbons

ethyne

IUPAC name of two triple bonded carbons, never used

Sub Alkanes

haloalkane

alcohol,

ethers,

aldehydes and ketones,

carb acids

amines

haloalkane

sub = halogen

lowest number

also named as alkyl halide (chloroethane or ethyl chloride)

alkyl halide

another way to name haloalkanes

alcohols

ending w/ -ol

lowest number possible

> DB and TB

also named as alkyl alcohol (ethanol or ethyl alcohol)

diols

AKA glycols

two OH

suffix diol

ethyl chloride

alkyl halide name for chloroethane

ethyl alcohol

common name of ethanol

isopropyl alcohol

common name 2 propanol

http://upload.wikimedia.org/wikipedia/commons/e/e1/2-Propanol.png

ethylene glycol

ethane-1,2-diol

http://upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Ethane-1,2-diol.svg/200px-Ethane-1,2-diol.svg.png

vicinal (vicinity)

diols w/ OH on adjacent

geminal (gemini)

OH on the same carbon

AKA hydrates

spon. lose water (dehydrate) => carbonyl compounds

ether

specified by alkoxy => presence of one (oxy) and corresponding smaller alkyl group (ex: oxy and alk-)

both connected to small O

ex: methoxyethane

common name of ether

two alkyl in alpha order + ether (ex: ethyl methyl ether)

cyclic ether common name

numbering of ring begin at oxygen following w/ lowest number for sub.

oxirane (ether)

3 membered ring (IUPAC)

epoxides

ethers as rings, common name

aldehyde

carbonyl

terminal, no numbering

end in "-al"

formaldehydge

common name for methanal

acetaldehyde

common name for ethanal

propionaldehyde

common name for propanal

ketone

end in '-one'

alkyl + ketone

as sub => oxo-

carbons away from carbonyl ordering

alpha, beta, gamma, delta

carboxylic acid

receives # 1

3 bonds to oxygen

most oxidized functional group (more than this is CO2, since 4 bonds to oxygen)

amines

N containing compounds, longest chain attached to N atom used as backbone

suffix is -amine

prefix is amino-

add. group attached to N => N-

P = carboxy

S = -oic acid

carboxylic acid P and S

P = alkoxycarbonyl

S= oate

ester P and S

P = halocarbonyl

S= -oyl halide


http://upload.wikimedia.org/wikipedia/commons/a/a6/Acyl_Halide.PNG

acyl halide P and S

P = amido

S= amide


http://upload.wikimedia.org/wikipedia/commons/8/8a/Amide-(primary)-skeletal.png

amide P and S

P = cyano

S= -nitrile

nitrile/cyanide P and S

P = oxo-

S= -al

aldehyde P and S

P = oxo-
S= -one

ketone P and S

P = hydroxy-

S= -ol

alcohol P and S

P = sulfhydrl-

S= -thiol


RSH

thiol P and S

P = amino-

S= -amine



RNH2

amine P and S

P = imino-

S= -imine


R2C=NR'

imine P and S

P = alkoxy-

S= -ether


ROR

ether P and S

P = alkylthio-


R2S

sulfide P and S

P = halo-

-I,-Br, -Cl,-F

halide P and S

P = nitro-

RNO2

nitro P and S

P = azido-

RN3

azide P and S

P = diazo -

RN2

diazo P and S

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