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56 terms

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