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CHM 2210C Lesson 5 September 12, 2022

Brianna D b
Group Members _____________________________________________________________________
i n
1. Circle all of the following Newman Projection Figures that represent the staggered conformation.

T
000
isomers that are in a gauche conformation and box all that are in an anti conformation.
Circle gauche Box anti
O
2. All of the following structures are in a staggered conformation. Circle all of the following rotational

0
00 08
3. Identify the longest continuous carbon chain length in each of the following Newman Projection
figures.

9
a) __________ 4
b) __________
6
c) __________ d) __________
6 e) __________
i
4. Convert each of the following Newman Projection figures to a Line Structure.
U
L

R
R
L R
I R

L
D
a) b) c) d)

mm

att iq 7 am

I
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5. Draw the precise Newman projection figure for each of the rotational isomers of the compounds
described below.
highest
a) The least stable
energyeclipse
conformer of heptane on the C2 – C3 bond.
b) The anti conformer of pentane.
c)

a) b) c)

T
I

MMA H
catgut
H I
Chato citzett
6. Draw the precise Newman projection figure for each of the rotational isomers of the compounds
described below.
staggered

Tineidae
a) The most stable conformer of octane on the C4 – C5 bond.
b) A gauche conformer of hexane.
c)

a) b) c)
it
Hy catty B
fat tats

It cheats't F
pl H

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7. Given below are the 6 rotational isomers of the C3 – C4 bond rotation of 2,3,4-trimethylhexane. Draw
the energy diagram for the complete 360o rotation.

staggered
Et Et Et
Et Pr Et
eclipse H Et

staggered 60o 60o

in
60o
high
H
Me Me Me PrMe Me Me
H Pr
0o; 360o Et
60o 120o
Et Et
Pr Pr H H

60o eaten60 o 60o

eat
Et Pr
Me H Me Me Me Me Et Me
o Et
300 o
240o 180
stagg
Energy

0 60 120 180 240 300 360

Angle of Bond Rotation

8. Draw the structure of:

a) a compound with a total of seven carbons with a ring that is significantly strained.
b) a compound with a total of seven carbons with a ring that has no ring strain.

E
9. Circle any structures in the following set that would be expected to show significant ring strain in
any portion of the molecule.

O o
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10. Provide a complete IUPAC name for each of the following compounds.
maymoral

i
as
s's Q 8
i O
Q dimetylery

É o
i tho

metblets
Ii amine

a) _______________________________________________________________________
1 methyl propylcyclohexane
b) _______________________________________________________________________
3 hexane
cyclopentane
c) _______________________________________________________________________
2 methylethyl 4 2 methylpropyl cyclopentanamire
d) _______________________________________________________________________
6 ethyl 3 dimethylethyl cycloheptano
G
e) _______________________________________________________________________
bromo 2 chloro S methyl cyclooctanore
f) _______________________________________________________________________
CIS l bromo 2 methyl cyclopropane
g) _______________________________________________________________________
trans l methoxy 2methylethylcyclobutare
h) _______________________________________________________________________
2,6 dimethyl cycloheptanamin
11. Calculate the unsaturation for each of the following chemical formulas. SHOW ALL WORK
I
a) C8H14O2 b) C7H7ClO c) C9H11N d) C26H20N4O4 e) C22H33N3O6

a) __________
2 b) __________
4 5
c) __________ d) __________
19 18
e) __________

Show Calculations Here U candLEH 0 221 E E

0 97 11 2
U D 01711
a 10 122
11 a
27 10 2
19
I3 is

12. Determine the unsaturation for each of the following structures.

3Is
a) _____________
10 Yt's
b) _____________ c) _____________
8 d) _____________
9rings

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13. Draw an acceptable structure for each of the following compounds.

a) butylcyclopentane b) cycloheptylmethanal
c) 2-chloro-3-methylcyclobutanol d) 4-bromo-2-ethylcyclohexanone
e) trans-4-methyl-1-(2-methylpropyl)cyclohexane f) cis-3-methylethylcyclooctanamine
g) cis, trans-2,4-dimethylcyclopentanol h) trans, trans, cis-3-chloro-2,5-dimethylcyclohexanol

a) b)

E
E

c) d)
OH

e) af a
f)
Bff
g)
III h)
Eta i
Éatector
CH CH

Eyman
Cfo É Eat

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14. Draw the two possible chair structures for the following substituted cyclohexane compounds.

a)

É'T
CH3

CH2CH3

dwn
b) q
chccitzz

H3C CH(CH3)2

IF
CH3
F
atcha
F
15. Provided below are the two possible chair structures of cyclohexane compounds. Circle the
structure that would be expected to be the most stable and provide a brief explanation for your
choice.
a)
H

o
H

CH3 H
H

Br Br CH3

no non hydrogens in axial position

b)
CH3
H

0
Cl
CH3 CH3
H
Br Cl
H H
CH3
H H
H
Br H

Bothhave 4 axial and a equatorial

opposite side In
but this one the axial pops are on
axial plate
the other structure the methyl groups in the interact
are on the same side and sterically
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