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Atom Connectivity
aldehyde
RCHO
(R = H, formaldehyde)
O
C
carboxylic acid
RCO2H
(R = CH3; acetic acid)
O
H
H C
H
H
H
Alkyl Halide
RX
Cl
H
Br
C
H
H H
Cl
Br
C
C
C
H
H
H
H
H
C
Sulfide
S-C-S
amine
RNH2
(R = C6H6; aniline)
H
H
C
C
Ester
RC(O)OR
O
H
H
ketone
R(CO)R
(R = CH3; acetone)
ether
ROR
(R = CH3CH2; diethyl ether)
C
N
C
C
H
C
C
H
H
O
H
H
H
H
H C
H
C
H
N
H
O
H
C H
H
H H H H
H
C
C
C
O
C
H
H
H
H
H
O H H
H
H C C O C C H
H
H H
O
H
H
H
H
C H
H
H
H H H H
H
C
H
C
C
C
O
H
H
H H
alcohol
ROH
(R = CH3CH2; ethanol)
H H
C
H
O
H C
H
H
H H
C
O
H
H
Aromatic hydrocarbons
(arene)
C6H6
For each compound below, draw the Lewis dot structure and the bond-line drawing.
Then build the compound using your model kit and draw the 3-d representation of the
structure.
1) Alkanes: When naming alkanes we need to indicate how many carbons are in the
longest carbon chain and indicate if there are any substituents. For alkane and halogen
substituents we start with the longest chain, and then give the number of the carbon to
which each substituent is attached.
a) 4-ethyl-3,4-dimethylnonane
b) 3-bromo-2-fluoro-5,6-dimethylheptane
2) Cyclic compounds cyclo indicate the presence of a ring. The suffix ene indicate
the presence of a double bond.
a) cyclohexane
chair conformation (we will talk about the different
conformations of cyclohexane next week).
cyclo-hexane
b) cyclo-hexatriene - What do you notice about the geometry of benzene versus
cyclohexane?
since all the carbons in benzene are sp2 hybridized, the ring is planar
(completely flat) whereas the sp3 hybridization in cyclohexane creates
nearly 109 angles at each carbon.
cyclo-hexatriene
c) 1,3-diethylcyclopentane
b) pentanal (notice that with aldehydes ( indicated by al suffix) the oxygen must be
terminal by definition, whereas you have to specifically indicate the position of most
other functional groups)
OH
(E)-3-phenylprop-2-enoic acid
The E or trans prefix on cinnamic acid tells us the orientation of the substituents
around the double bond that starts at the 2nd carbon. Trans means the highest priority
substituents are on opposite sides. We will talk much more about this once we get into
isomers.
sp
sp3
NH2
sp3
(note: each carbon in the phenyl ring is sp2 hybridized)