Prep 101 Booklet
Your
Conptiüve Edç
urlptlrÊ s'tuDrlt'ts stltf,r
ljr-Jl-,rüs
tp,qql
J::rjthj
Ghem2l2e*a McGill University* *Prepl01 is not affiliated with the university
---
,;y$ï*xÂard I
L+{
1""+-++
,r.+a++
u,Eucomuro PBEPlorr To maximize the benefits for everyone attending this prep session, we encourage you
to:
B€ ACnVE learners:
o
Pay close
.
Keep up a positive attitude. You con do thisl
o
.
Show
attention and concentrate.
Ask a question if anything is unclear. Don,t forget, however, that you,re at a prep session - not one-on-one tutoring. lf your question isn't directly related to what the instructor is covering, save it for an email after the p.ep session. Practice, practice, practicel Tackle the practice questions in the course Booklet and past Exams (if applicablel before you look at the online solutions. we'll get you off to a great start by showing you rots of herpfur probrem-solving methods, strategies, and tips. But it's ultimately up to you to grind it out and put in the hours of practice. RESPECT
to your instructor and classmates:
o
Turn off your cell-phone.
o
Don'ttalk among yourselves and disrupt the learning environment.
o
Put trash in garbage bins.
o
Don',t stampede the instructor at Breaks. The instructor needs space freshen up and get ready for the next lnstruction period.
Give CONSTRUCTTVE feedback:
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& §(x)D LUCK Ull[rr YouR srupmsr
at
Breaks to
chem212 Exam Booklet
OPrep101
PREP SESSION OUTLINE Part 1 (5:30pm-9:30pm) Mclntyre 504 lU9!9: We'll start 15 minutes late (and end 15 minutes late) to give everyone time to sign in and pick up course materials.l
5:30-5:45 5:45-7:00 7:OO-7iLO 7:10-8:30 8:30-8:40 8:40-9:30
lntroduction 1st lnstruction Period Break 2nd lnstruction Period Break 3rd lnstruction Period
Part 2 (9:00am-l:00pm) tEA 26
9:00-10:30 10:30-10:40 1O:40-12:0O t2:OO-12:tO 12:10-1:00
4th lnstruction Period Break
5th lnstruction period Break
6th lnstruction Period
Part 3 (9:00am-1:00pm) tEA 26
9:00-10:30 10:30-10:40 IO:4O-L2:OO !2:OO-72:LO 12:10-1:O0
7th lnstruction Period Break
8th lnstruction period Break
9th lnstruction Period
Solutions will be posted at www'preplOl.com/solutions
Chem212 Exam Booklet
@PreP101
PreP 101 PreP Session CHEM 212 Final Exam
Preface
copyright A Friendly Note about not please respect that by lwould ask that you work of hours represents many This Course Booklet
copyinganypartofthisb""k'Y;;;;welcometosharethisbookwithyourfriends'butpleasedon't coPY!
Thanks a lot' -Laura Dodge Ph D Candidate McMaster University
How to Reach Me Email address: laura'c'dodoe@omail'com
Don,thesitatetoe.mailmewithanyquestionsthatyouhaveaboutthisbooklet,thepreviousexams, or any other organic chemistry questions that you have!
Solutions will be posted at www.prepl0l.com/solutions
a
Chem212 Exam Booklet OPreP101
Table of Contents
2 7
Sheet 2012 CHEM 212 StudY and Bonding Theories
#t,";
12
;."''uo'"n"'"'u'"
12 14
'1.1
1.2
Bonding Theories
26
1.3
Formal Charges
27
Practice Problems 30 Analysis ot Alkanes 30 ChaPter Two: Conformational Alkanes of Conformational Analysis 32 2.1 of Cylcoalkanes analysis Conformational 35 2.2 1,3-diaxial interactions " " 36 2.3 lsomerism " " " " " " " " " Cis-Trans Disubstituted Cycloalkanes: 2.4 --37 ' " Practice Problems 2.5 42 Chapter Three: Stereochemistry 42 Chirality of Objects and Enantiomers 3.1 43 Chiral Carbon Atoms 3.2 1.4
Formulas
"""'44
3.3
Fisher Projection
3.4
Nomenclature of Stereoisomers - Naming Enantianomers.... 45
3.5
Rotation of Plane-Polarized Light
49
3.6 3.7
Meso Compounds
3.8
Basic summary
3.9
Absolute vs. Relative
3.10
Resolution
-
55
Configuration.
................ 56
the Separation of a Racemic Mixture into its
Enatiomers 3.'t1
Axial Chirality
3.'12
Practice Problems rvvr9rttù.,.rr,..!
58 .............59
ChapterFour:SubstitutionandEliminationReactions...... Solutions will be posted at www.preplOl.com/solutions
.........66
@Prep101
Chem212 Exam Booklet
!+.tb
practice problems.......
Chapter Five: Alkenes........
"""""""
.
............106
Alkenes.....
5.1
Preparation of
5.2
Alkene Stability and Heats of Hydrogenation:.......................
5.3 5.4
Alkenes Practice Problems.......
6.1
Naming
6.2 6.3 6.4
7.2 7.3
........ 106
Reactions of
1
06
...............1o1 ............. 113
Alkynes Preparation of Alkynes Reactions of Alkynes...... Practice Problems.......
......-.-.--...........123
Benzene""
"""""'130
Chapter Seven: Chemistry of 7.1
95
Benzene Nomenclature of aromatics Aromatic vs. Non-aromatic." """"""
The Structure of
Solutions will be posted at www'prep1O1'com/solutions
""""""'
'
123
"""""'|-25 .""""'128
"""'
"
130
' 13't
""""'132
Chem212 Exam Booklet
7.4 7 .5
substitution Electrophilic aromatic
"""' Terpenes Appendix: lsoprene and practice Problem: EXAMWRIrINGT|PS" """ Multiple Choicelips """ """'
(EAS)"""" """"""" ""
"""""
Practice Problems
134
" 149 .
lt8
160 ""' lun
"
"
Solutions will be posted at www.prep101.com/solutions
"""
160
5
@preplOl
Chem212 Exam Booklet
Welcome to prep 101 lot CHËM 212!
is inrended to provide an overview or the recrure ;t:#i::.:T:: :iï1,ïsis notrecrure, materiar possible in such a short period of
time to cover, in depth, every
topic discussed during the col
îîï::Jffi'tr;;:Hr1f:iili;Jliiîll^,î;ï:'ïîï:":ï#ï: hope thar
the recrure rhis is done
the,,"
\rynh
rhe famitiar studenrs wi become materiat, and wi be",.;r;";;;:ffi:i"::i:i"ïîi::1",i". with thar abte
,n,,^
on teachins student
"r-,^"^":l::,*" examination situation. rhe " "O*o j|:trI",T:H:.ï recrure ,,, ..u" r,o*,o ,r lo answêr questions "f'jf correcfly.
Good luck!
Solutions will be posted at www.prep101'com/solutions
b
Booklet chem212 Exam @PreP101
Sheet 2012 CHEiJI 212 Study Stereochemistry chiral I{lolecules: Achiral Molecules: Oltical rotatbn:
Non-superimposable svmmetry' Motecute witn
'plâne of other with no each of mirror images
, pl"n" of .ÿ.m"§*rrl[p rctaüon (deg
aütength @m)
x
IalD = Iobseved (ÿrnL)l concentraüon
opposite fomuta' same connectivîty' sdme motecutar
Enantiomers:
centres' f,tJn"n"'i"uv at ALL stereogan:tc
opposite stereochemistry
Diastereomers:
:is,,Ë[:ï :iï,:#::i":il8#:ÏdMtv'
Meso compounds
inaCtiVê A stereoisomer, with two or more stereocenires, tnat is optically due to a Plane of symmetry.
Racemicmixtures:Equat(50:50)mixturesottwoenantiomers;ofrendenotedby(+1.).
t
Don't confuse (+) or C) with R or
S.
(+) or G) designate the
direction of rotation of polarized light in the molecule. 7o
enantiomeric excess (e.e)
=
= Assi gning stereochem istry:
moles of one enantiomer - rnoles of other enantiomer X 100 Total moles of both enantiomer
rotation
observed specific X 100 Specific rotation of pure enantiomer
Rank substituents according to the cahn{ngord-prelog rules (higher the atomic number,
highertheprroritv),andrheaimlowestrankedàwayfrom-theviewèrli.e.irrotnepàjuj.-'--''
)
lf the remaining 1"i, 2"d and 3d ranked substituents are arranged: (i) Clockwise: (ii) Counter clockwise:
R Stereochemistry
S Stereochemistry
,.,",.-ï
"\ -o..
\ /"" '*"Y )
"">HO-R)
Relative Reactivity of Leaving Group (LG)
l- >
-oH >'NH2> R3c' Br > Cl> F and Polar aprotic solvents to cations but not anions, leaving Nu unsolvaled
Polar protic solvents to stabilize cations and anions
n the conesponding
coniugate acid -NHz>>NHs and HO>>HzO
NucleophilicitY
ln the same rovÿ, nucleophilicity parallels basicity RgC'>R2N'>RO->F' No carbocation intermediate = no
intermediate = caPable of rearrangement
Alkene stability:
*\
RR
\-,/
R.R
>
):(
\* 3 R gloups
R/
4 R grouPs
,r^
- ^\-,/n
\* 2 R groùPs trans
nl
rearrangement
*\-,/" ,t'
'H
2 R grouPs
crs
Zaitsey's rüle: form the most stable double bond
Solutions will be posted at www'prep101'com/solutions
I
Chem212 Exam Booklet
@PreP101
s§'/
s"1!sllE (l) wear uasevgood t-o sn2flnn Nu' E1 with good LG' weak
SN2 mainlY
iiotic
.
polar cariocatioÀ rearrangement'. near and Protic solvent
E2 with strong hindered bases ('Buo'), Polar
Addiüon Reactior,s
solvent, weak Nu/base (and heat lor E'l )
E, with strong base' Polar heal àProtic solvent and
F. with strong bases (RO')' Polar aprotic solvent and heat
aprotic solvent and heat
Dibromination
HYdrogenation i i
n
\:1 / \
Hy'Pd4>-r-\'
^\-'
No S"2
s..1 & E1 with good LG' Polar
*/--.--',
.H
Brz ccr4
ÉH
syn
.
Addition of HX
RHHBTR
,>
O ^
/.Vl'tO. ll
\2
I
RCr
R I
^"-O H2soa fi1'sosn +\2
o
4", Alcl3
c^.
Solutions will be posted at www.prepl0l'com/solutions
10
Chem212 Exam Booklet
OPrePlOl
Strongly activating
Side Chain Reactions:
KMnOa, HzO
t_
Oxidation:
\)
ù'o'*
d" Br
Halogenation:
NBS
ù* 3cl2'hvorheat
Ü
ry"o"
Solutions will be posted at www.prepl0l.com/solutions
1'l
@prep1O1
chem212 Exam Bookler
Chapter One: Nomenctature and Bonding Theories Nomenctature
1.1
1.1.1 Ctassification of Hydrogên & Carbon Atoms
.
Hydrogen atoms ar
,,:f il;i:ï:,ii:i1y':â;,,il:i^iî::::i,Éîi:ïii;i,ïiiTiï,itî?X',,,.i,î
. . .
primary
C (1")
)
secondary c (2.)
.
Tertiary
C:
with 1 c-c bond with 2 c-c bonds
)"bon
"'(3:il'"'r-::"on o,"t",",.vt',.:,î':::riiin'i"jl,lio.
1.1.2 Alkanês & Cycloalkanes 1.
2.
Select the longest continuous c t'tumoer tne
,rortit*ntJ;;:il'
3.
ro"ntrv
4.
,sam:
Locate
5.
Put substituents in
kind ,,
6.
of carbon atoms for the basic name.
ca-rr;n-sî;;#1'*,r ,,","n,,
,,l ,n"lJl,liT
he substituents by the nr
separate numbers ",,n"*r,"",
rrom;;
basic name at the end.
the end nearest the rirsr branch.
.'I*r
:ïil;:,ï:]
'
more than one substituent or the
of the carbon to which they are aftached.
ilii:l''fi'J,iïiîlî:^1"
""
one word with the
Note on Nomenclafure: Common Groups Found in Organic Molecutes
Y
\._ tl I _.,,I
ÿ\./\,r\./.
I
I
Isopropyl Group
.ÿec-butyl group
I _-----__-/y
:f I
'€rl-butyl
group
isobutyl group
Z-=,i Phenyl Group
Benzyl Croup
Allyl Group
Solutions will be posted at www'prep101'com/solutions
12
Booklet Chem212 Exam @PreP101
of Complex Substituents 1.1.3 Nomenclature identify to the main chain' X""ned caoon tn" with
r
stafling
substituent
the cârbon atoms in cha,n sivins the
,
i,,*,,ne
3'
of the longest chain
1' chain the number
carîî::l'Tiü:,::iiji*l*ruv€re
attached
ldentity substituents mai , .rostituent on the substl ", Treat the complex which it is to \^'hich it is carbon of the carbon to the of number $ re number by preceded subst[uent in brackets Place lhe complex
1Tnil
4.
attâdled'
5.
attached.
the brâckets The first letter inside
6.
lt' §ffï:":|'n""i:Ï:::
^^ :in âlphabetizati ^r^trarreiiztion coun§
prefix' even if it iS a multiplier
carbon bearins the which contains the atoms carbon or chain
hydroxÿ group'
alkane from the -€ne of the conesponding Change the ending to -ol the carbon bearing he 'OH' chain from the endnearest Number the carbons in the it is attached' the number of the cârbon to wTlich Locate the posiüon of the -oH by
2. 3. 4. 5. 1.1
Name substituents as with alkanes
.5
.1.
Nomenclature ot Alkenes and Cycloalkenes Select the longest continuous chain of carbon atoms which contains both carbons of the double bond for the bâsic name.
2. 3. 4
Change the ending to -ene from the -ane of the corresponding alkane Number the carbons in the châin from the end nearest the first carbon of the double bond. Locâle the position of the double bond by the number of the first carbon involved in the double bond.
5. 6. 7'
Name substituents es with alkanes ln a cyclic system number the cârbons of the double bond as 1 and 2. lf two identical groups are on the sâme side of the double bond, the alkene is designated cis. rf two identicar groups are on opposite sides of the doubre bond, the arkene is designated lrans:
H-
)":
Conptiüve Edç
urlptlrÊ s'tuDrlt'ts stltf,r
ljr-Jl-,rüs
tp,qql
J::rjthj
Ghem2l2e*a McGill University* *Prepl01 is not affiliated with the university
---
,;y$ï*xÂard I
L+{
1""+-++
,r.+a++
u,Eucomuro PBEPlorr To maximize the benefits for everyone attending this prep session, we encourage you
to:
B€ ACnVE learners:
o
Pay close
.
Keep up a positive attitude. You con do thisl
o
.
Show
attention and concentrate.
Ask a question if anything is unclear. Don,t forget, however, that you,re at a prep session - not one-on-one tutoring. lf your question isn't directly related to what the instructor is covering, save it for an email after the p.ep session. Practice, practice, practicel Tackle the practice questions in the course Booklet and past Exams (if applicablel before you look at the online solutions. we'll get you off to a great start by showing you rots of herpfur probrem-solving methods, strategies, and tips. But it's ultimately up to you to grind it out and put in the hours of practice. RESPECT
to your instructor and classmates:
o
Turn off your cell-phone.
o
Don'ttalk among yourselves and disrupt the learning environment.
o
Put trash in garbage bins.
o
Don',t stampede the instructor at Breaks. The instructor needs space freshen up and get ready for the next lnstruction period.
Give CONSTRUCTTVE feedback:
.
Add written comments on Evaluations to help us improve our service.
THÀNK YOU rON cII(x)§IN§ PNEPIOr
& §(x)D LUCK Ull[rr YouR srupmsr
at
Breaks to
chem212 Exam Booklet
OPrep101
PREP SESSION OUTLINE Part 1 (5:30pm-9:30pm) Mclntyre 504 lU9!9: We'll start 15 minutes late (and end 15 minutes late) to give everyone time to sign in and pick up course materials.l
5:30-5:45 5:45-7:00 7:OO-7iLO 7:10-8:30 8:30-8:40 8:40-9:30
lntroduction 1st lnstruction Period Break 2nd lnstruction Period Break 3rd lnstruction Period
Part 2 (9:00am-l:00pm) tEA 26
9:00-10:30 10:30-10:40 1O:40-12:0O t2:OO-12:tO 12:10-1:00
4th lnstruction Period Break
5th lnstruction period Break
6th lnstruction Period
Part 3 (9:00am-1:00pm) tEA 26
9:00-10:30 10:30-10:40 IO:4O-L2:OO !2:OO-72:LO 12:10-1:O0
7th lnstruction Period Break
8th lnstruction period Break
9th lnstruction Period
Solutions will be posted at www'preplOl.com/solutions
Chem212 Exam Booklet
@PreP101
PreP 101 PreP Session CHEM 212 Final Exam
Preface
copyright A Friendly Note about not please respect that by lwould ask that you work of hours represents many This Course Booklet
copyinganypartofthisb""k'Y;;;;welcometosharethisbookwithyourfriends'butpleasedon't coPY!
Thanks a lot' -Laura Dodge Ph D Candidate McMaster University
How to Reach Me Email address: laura'c'dodoe@omail'com
Don,thesitatetoe.mailmewithanyquestionsthatyouhaveaboutthisbooklet,thepreviousexams, or any other organic chemistry questions that you have!
Solutions will be posted at www.prepl0l.com/solutions
a
Chem212 Exam Booklet OPreP101
Table of Contents
2 7
Sheet 2012 CHEM 212 StudY and Bonding Theories
#t,";
12
;."''uo'"n"'"'u'"
12 14
'1.1
1.2
Bonding Theories
26
1.3
Formal Charges
27
Practice Problems 30 Analysis ot Alkanes 30 ChaPter Two: Conformational Alkanes of Conformational Analysis 32 2.1 of Cylcoalkanes analysis Conformational 35 2.2 1,3-diaxial interactions " " 36 2.3 lsomerism " " " " " " " " " Cis-Trans Disubstituted Cycloalkanes: 2.4 --37 ' " Practice Problems 2.5 42 Chapter Three: Stereochemistry 42 Chirality of Objects and Enantiomers 3.1 43 Chiral Carbon Atoms 3.2 1.4
Formulas
"""'44
3.3
Fisher Projection
3.4
Nomenclature of Stereoisomers - Naming Enantianomers.... 45
3.5
Rotation of Plane-Polarized Light
49
3.6 3.7
Meso Compounds
3.8
Basic summary
3.9
Absolute vs. Relative
3.10
Resolution
-
55
Configuration.
................ 56
the Separation of a Racemic Mixture into its
Enatiomers 3.'t1
Axial Chirality
3.'12
Practice Problems rvvr9rttù.,.rr,..!
58 .............59
ChapterFour:SubstitutionandEliminationReactions...... Solutions will be posted at www.preplOl.com/solutions
.........66
@Prep101
Chem212 Exam Booklet
!+.tb
practice problems.......
Chapter Five: Alkenes........
"""""""
.
............106
Alkenes.....
5.1
Preparation of
5.2
Alkene Stability and Heats of Hydrogenation:.......................
5.3 5.4
Alkenes Practice Problems.......
6.1
Naming
6.2 6.3 6.4
7.2 7.3
........ 106
Reactions of
1
06
...............1o1 ............. 113
Alkynes Preparation of Alkynes Reactions of Alkynes...... Practice Problems.......
......-.-.--...........123
Benzene""
"""""'130
Chapter Seven: Chemistry of 7.1
95
Benzene Nomenclature of aromatics Aromatic vs. Non-aromatic." """"""
The Structure of
Solutions will be posted at www'prep1O1'com/solutions
""""""'
'
123
"""""'|-25 .""""'128
"""'
"
130
' 13't
""""'132
Chem212 Exam Booklet
7.4 7 .5
substitution Electrophilic aromatic
"""' Terpenes Appendix: lsoprene and practice Problem: EXAMWRIrINGT|PS" """ Multiple Choicelips """ """'
(EAS)"""" """"""" ""
"""""
Practice Problems
134
" 149 .
lt8
160 ""' lun
"
"
Solutions will be posted at www.prep101.com/solutions
"""
160
5
@preplOl
Chem212 Exam Booklet
Welcome to prep 101 lot CHËM 212!
is inrended to provide an overview or the recrure ;t:#i::.:T:: :iï1,ïsis notrecrure, materiar possible in such a short period of
time to cover, in depth, every
topic discussed during the col
îîï::Jffi'tr;;:Hr1f:iili;Jliiîll^,î;ï:'ïîï:":ï#ï: hope thar
the recrure rhis is done
the,,"
\rynh
rhe famitiar studenrs wi become materiat, and wi be",.;r;";;;:ffi:i"::i:i"ïîi::1",i". with thar abte
,n,,^
on teachins student
"r-,^"^":l::,*" examination situation. rhe " "O*o j|:trI",T:H:.ï recrure ,,, ..u" r,o*,o ,r lo answêr questions "f'jf correcfly.
Good luck!
Solutions will be posted at www.prep101'com/solutions
b
Booklet chem212 Exam @PreP101
Sheet 2012 CHEiJI 212 Study Stereochemistry chiral I{lolecules: Achiral Molecules: Oltical rotatbn:
Non-superimposable svmmetry' Motecute witn
'plâne of other with no each of mirror images
, pl"n" of .ÿ.m"§*rrl[p rctaüon (deg
aütength @m)
x
IalD = Iobseved (ÿrnL)l concentraüon
opposite fomuta' same connectivîty' sdme motecutar
Enantiomers:
centres' f,tJn"n"'i"uv at ALL stereogan:tc
opposite stereochemistry
Diastereomers:
:is,,Ë[:ï :iï,:#::i":il8#:ÏdMtv'
Meso compounds
inaCtiVê A stereoisomer, with two or more stereocenires, tnat is optically due to a Plane of symmetry.
Racemicmixtures:Equat(50:50)mixturesottwoenantiomers;ofrendenotedby(+1.).
t
Don't confuse (+) or C) with R or
S.
(+) or G) designate the
direction of rotation of polarized light in the molecule. 7o
enantiomeric excess (e.e)
=
= Assi gning stereochem istry:
moles of one enantiomer - rnoles of other enantiomer X 100 Total moles of both enantiomer
rotation
observed specific X 100 Specific rotation of pure enantiomer
Rank substituents according to the cahn{ngord-prelog rules (higher the atomic number,
highertheprroritv),andrheaimlowestrankedàwayfrom-theviewèrli.e.irrotnepàjuj.-'--''
)
lf the remaining 1"i, 2"d and 3d ranked substituents are arranged: (i) Clockwise: (ii) Counter clockwise:
R Stereochemistry
S Stereochemistry
,.,",.-ï
"\ -o..
\ /"" '*"Y )
"">HO-R)
Relative Reactivity of Leaving Group (LG)
l- >
-oH >'NH2> R3c' Br > Cl> F and Polar aprotic solvents to cations but not anions, leaving Nu unsolvaled
Polar protic solvents to stabilize cations and anions
n the conesponding
coniugate acid -NHz>>NHs and HO>>HzO
NucleophilicitY
ln the same rovÿ, nucleophilicity parallels basicity RgC'>R2N'>RO->F' No carbocation intermediate = no
intermediate = caPable of rearrangement
Alkene stability:
*\
RR
\-,/
R.R
>
):(
\* 3 R gloups
R/
4 R grouPs
,r^
- ^\-,/n
\* 2 R groùPs trans
nl
rearrangement
*\-,/" ,t'
'H
2 R grouPs
crs
Zaitsey's rüle: form the most stable double bond
Solutions will be posted at www'prep101'com/solutions
I
Chem212 Exam Booklet
@PreP101
s§'/
s"1!sllE (l) wear uasevgood t-o sn2flnn Nu' E1 with good LG' weak
SN2 mainlY
iiotic
.
polar cariocatioÀ rearrangement'. near and Protic solvent
E2 with strong hindered bases ('Buo'), Polar
Addiüon Reactior,s
solvent, weak Nu/base (and heat lor E'l )
E, with strong base' Polar heal àProtic solvent and
F. with strong bases (RO')' Polar aprotic solvent and heat
aprotic solvent and heat
Dibromination
HYdrogenation i i
n
\:1 / \
Hy'Pd4>-r-\'
^\-'
No S"2
s..1 & E1 with good LG' Polar
*/--.--',
.H
Brz ccr4
ÉH
syn
.
Addition of HX
RHHBTR
,>
O ^
/.Vl'tO. ll
\2
I
RCr
R I
^"-O H2soa fi1'sosn +\2
o
4", Alcl3
c^.
Solutions will be posted at www.prepl0l'com/solutions
10
Chem212 Exam Booklet
OPrePlOl
Strongly activating
Side Chain Reactions:
KMnOa, HzO
t_
Oxidation:
\)
ù'o'*
d" Br
Halogenation:
NBS
ù* 3cl2'hvorheat
Ü
ry"o"
Solutions will be posted at www.prepl0l.com/solutions
1'l
@prep1O1
chem212 Exam Bookler
Chapter One: Nomenctature and Bonding Theories Nomenctature
1.1
1.1.1 Ctassification of Hydrogên & Carbon Atoms
.
Hydrogen atoms ar
,,:f il;i:ï:,ii:i1y':â;,,il:i^iî::::i,Éîi:ïii;i,ïiiTiï,itî?X',,,.i,î
. . .
primary
C (1")
)
secondary c (2.)
.
Tertiary
C:
with 1 c-c bond with 2 c-c bonds
)"bon
"'(3:il'"'r-::"on o,"t",",.vt',.:,î':::riiin'i"jl,lio.
1.1.2 Alkanês & Cycloalkanes 1.
2.
Select the longest continuous c t'tumoer tne
,rortit*ntJ;;:il'
3.
ro"ntrv
4.
,sam:
Locate
5.
Put substituents in
kind ,,
6.
of carbon atoms for the basic name.
ca-rr;n-sî;;#1'*,r ,,","n,,
,,l ,n"lJl,liT
he substituents by the nr
separate numbers ",,n"*r,"",
rrom;;
basic name at the end.
the end nearest the rirsr branch.
.'I*r
:ïil;:,ï:]
'
more than one substituent or the
of the carbon to which they are aftached.
ilii:l''fi'J,iïiîlî:^1"
""
one word with the
Note on Nomenclafure: Common Groups Found in Organic Molecutes
Y
\._ tl I _.,,I
ÿ\./\,r\./.
I
I
Isopropyl Group
.ÿec-butyl group
I _-----__-/y
:f I
'€rl-butyl
group
isobutyl group
Z-=,i Phenyl Group
Benzyl Croup
Allyl Group
Solutions will be posted at www'prep101'com/solutions
12
Booklet Chem212 Exam @PreP101
of Complex Substituents 1.1.3 Nomenclature identify to the main chain' X""ned caoon tn" with
r
stafling
substituent
the cârbon atoms in cha,n sivins the
,
i,,*,,ne
3'
of the longest chain
1' chain the number
carîî::l'Tiü:,::iiji*l*ruv€re
attached
ldentity substituents mai , .rostituent on the substl ", Treat the complex which it is to \^'hich it is carbon of the carbon to the of number $ re number by preceded subst[uent in brackets Place lhe complex
1Tnil
4.
attâdled'
5.
attached.
the brâckets The first letter inside
6.
lt' §ffï:":|'n""i:Ï:::
^^ :in âlphabetizati ^r^trarreiiztion coun§
prefix' even if it iS a multiplier
carbon bearins the which contains the atoms carbon or chain
hydroxÿ group'
alkane from the -€ne of the conesponding Change the ending to -ol the carbon bearing he 'OH' chain from the endnearest Number the carbons in the it is attached' the number of the cârbon to wTlich Locate the posiüon of the -oH by
2. 3. 4. 5. 1.1
Name substituents as with alkanes
.5
.1.
Nomenclature ot Alkenes and Cycloalkenes Select the longest continuous chain of carbon atoms which contains both carbons of the double bond for the bâsic name.
2. 3. 4
Change the ending to -ene from the -ane of the corresponding alkane Number the carbons in the châin from the end nearest the first carbon of the double bond. Locâle the position of the double bond by the number of the first carbon involved in the double bond.
5. 6. 7'
Name substituents es with alkanes ln a cyclic system number the cârbons of the double bond as 1 and 2. lf two identical groups are on the sâme side of the double bond, the alkene is designated cis. rf two identicar groups are on opposite sides of the doubre bond, the arkene is designated lrans:
H-
)":
