Chem33 Extra Practice for Week 1

nomenclature, lewis dot structures, and bond-line notation

Functional Group Name

Atom Connectivity

aldehyde
RCHO
(R = H, formaldehyde)

Best Lewis Structure

O

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

d) cyclopropane What do you notice when building the model of cyclopropane

compared to larger rings? What conclusions could you draw about the potential
reactivity of these molecules?
When building a model you probably notice that you really have to force the atoms
together in order to make such a small ring this is the ring strain that Prof. Wender
mentioned in class, which makes these molecules very reactive.

3) Functional groups As the name implies, functional groups have a characteristic

reactivity. They are indicated by a suffix at the end of a parent chain, after any
unsaturation (ene or yne).
a) 1-pentanol

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)

c) 2-methylpropan-2-ol (also known as tert-butyl-alcohol)

bond-line notation
3-D representation
H
O

d) Cadaverine (which is a toxic and foul-smelling compound produced by protein

hydrolysis during putrefaction of animal tissue. The formula NH2(CH2)5NH2.
What is the formal name for Cadaverine?
1,5-pentanediamine or pentamethylenediamine.

e) Cinnamic acid (trans-3-phenylprop-2-enoic acid ) is used in flavors, synthetic indigo,

and certain pharmaceuticals, though its primary use is in the manufacturing of esters for
the perfume industry. Cinnamic acid has a "honey, floral odor" it is a flavor component in
the essential oil of cinnamon
O

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.

4) Phenylalanine is one of the essential amino acids - An essential amino acid is an

amino acid that cannot be synthesized de novo by the organism (usually referring to
humans), and therefore must be supplied in the diet. Phenylalanine is found naturally in
the breast milk of mammals. It is used in the manufacture of food and drink products and
sold as a nutritional supplement for its reputed analgesic and antidepressant effects.
The IUPAC name for Phenylalanine is 2-amino-3-phenylpropanoic acid.
Draw the bond-line drawing and then label the hybridization on each non-hydrogen atom
in Phenylalanine.
sp2
sp3
O
sp2
sp3
sp2
OH

sp

sp3

NH2

sp3
(note: each carbon in the phenyl ring is sp2 hybridized)