1) a) Define 'superimposable'. b) True or false: the structures at right are superimposable. CI Br H3C. CI Br CH3 H.

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1) a) Define 'superimposable'.
b) True or false: the
structures at right are
superimposable.
CI Br
H3C.
CI
Br
CH3
H.
2) When n-butane undergoes free-radical chlorination, THREE products are formed. ALL HAVE MF =
CAH»Cl and a 4-carbon straight chain! One is achiral and two are a pair of enantiomers.
i)
Draw their structures. You need only add the chlorine atom, but: any CHIRAL molecules MUST be
drawn with DASHES and/or WEDGES. CIRCLE THE PAIR OF ENANTIOMERS.
Cl
hv
1
23 4
123 4
123
Chiral or achiral?
Chiral or achiral?
Chiral or achiral?
3) Using DASHES and/or WEDGES for the bromines, draw the following:
A)
B)
a diastereomer of
cis-1,3-dibromocyclohexane
Now add the appropriate
Property Labels as you did
in Boxes A and B to this
structure.
cis-1,3-dibromocyclohexane
a constituional isomer of
cis-1,3-dibromocyclohexane
What Property Labels can you The Property Label step you want
here is to number the substituents
on the ring. This will tell you have
in fact draw a constitutional isomer.
Add the numbers to this structure.
add to this structure that tells
you the Br's are in fact cis?
Add them to this structure.
Draw the structures (ECSF) below, identify which is a 'resonance-stabilized O-minus' (RSOM) and which
is a 'non resonance-stabilized O-minus' ('NRSOM'). Which is a weak base and which is a strong base?
The rule for 'Exploded Condensed Structural Formula' (ECSF): Show ALL LONE PAIRS AND
FORMAL CHARGE. Leave sp' C-H groups condensed but DRAW OUT all OTHER functional groups.
4)
Ethoxide ion, CH,CH209
RSOM or NROSOM?
WB or SB?
Acetate ion, CH3CO2
RSOM or NROSOM?
WB or SB?
Transcribed Image Text:1) a) Define 'superimposable'. b) True or false: the structures at right are superimposable. CI Br H3C. CI Br CH3 H. 2) When n-butane undergoes free-radical chlorination, THREE products are formed. ALL HAVE MF = CAH»Cl and a 4-carbon straight chain! One is achiral and two are a pair of enantiomers. i) Draw their structures. You need only add the chlorine atom, but: any CHIRAL molecules MUST be drawn with DASHES and/or WEDGES. CIRCLE THE PAIR OF ENANTIOMERS. Cl hv 1 23 4 123 4 123 Chiral or achiral? Chiral or achiral? Chiral or achiral? 3) Using DASHES and/or WEDGES for the bromines, draw the following: A) B) a diastereomer of cis-1,3-dibromocyclohexane Now add the appropriate Property Labels as you did in Boxes A and B to this structure. cis-1,3-dibromocyclohexane a constituional isomer of cis-1,3-dibromocyclohexane What Property Labels can you The Property Label step you want here is to number the substituents on the ring. This will tell you have in fact draw a constitutional isomer. Add the numbers to this structure. add to this structure that tells you the Br's are in fact cis? Add them to this structure. Draw the structures (ECSF) below, identify which is a 'resonance-stabilized O-minus' (RSOM) and which is a 'non resonance-stabilized O-minus' ('NRSOM'). Which is a weak base and which is a strong base? The rule for 'Exploded Condensed Structural Formula' (ECSF): Show ALL LONE PAIRS AND FORMAL CHARGE. Leave sp' C-H groups condensed but DRAW OUT all OTHER functional groups. 4) Ethoxide ion, CH,CH209 RSOM or NROSOM? WB or SB? Acetate ion, CH3CO2 RSOM or NROSOM? WB or SB?
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