1-9
*pg 4-5-Nelson Chem 12
2
Naming alkanes:
practice 1&2
*pg 15-16- Nelson Chem 12
3.
5. Name the following organic compounds using the IUPAC system of nomenclature
a) C2H5–CCl2–CH=C(CH3)–CH2–CH3
a) 5,5-dichloro-3-methyl-3-heptene
b) CH2–CC–C(NO2)–CBr–CH3
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C3H7
CH3
CH3
b) 2-bromo-3-nitro-2,3-dimethyl-4-nonyne
CH3 C2H5
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c)
C2H5–C(NH2)–CI–CH3
d) CHI2–CBr2–CCl2–CH3
e) CF2=CF2
c) 3-amino-4-iodo-2,3-dimethyl
d) 2,2-dibromo-3,3-dichloro- e) 1,1,2,2-tetrafluoroethene
hexane
1,1-diIodobutane
f)
g) CH=C-CH(CH3)-CH3
CH3
NC-
Cl
h)
C3H7
Cl
CH-CH3
CH3
Br CH3
f) 3-cyano cis-1,2-di
g) cis-1,2-di(2-chlorocyclobutyl) h) 5-bromo-1-cyclopropyl-3-propylmethylcyclopentene
-3-methyl-1-butene
4-isopropylcyclohexene
i) CH3–CH(NO2)–CH(NO2)–CH(NO2)–C2H5 j) CH3–CH – CH–CH3 k) CH2=CH–CH=CH2
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.................................................................................................
CH3–CH2 CH2–C2H5
i) 2,3,4-trinitro-2-methylcyclohexane
l) H5C2 C2H5
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CF=CF
3,4 -difluoro.
hexane.
j)
k)
1,3-butadiene
n) NH2–(CH2)6– NH2
m)
CH3
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CH2=C–CH=CH2
2-methyl-1,3butadienne
3,4-dimethylheptane
1,6 diaminohexane........
*o) (CH3–CHI-CHCl)2–CH–CH3
.
3,5-dichloro-2,6-diIodo-4-methylheptane
.........................................................…...............................
6. Draw correct structural diagrams for the following molecules
a)
c)
e)
g)
i)
k)
m)
o)
q)
1-bromo-1-chloro-2-methylpropane
1-bromo-2-nitropentane
3,3-diethyl-4-methy-5-isopropylloctane
2-methyl-1,1-dicyclopropyl-1-propene
trans-3,4-dimethyl-3-hexene
3-cyclopropyl-1-pentene
1,2-dicyclopropylethane
cis-3,4-diamino-1,3,5-heptatriene
3,3,3-trichloropropene
a) CHBrCl–CH(CH3)–CH3
b)
d)
f)
h)
j)
l)
n)
p)
r)
3-ethyl-2-methylheptane
2,3,3,4-tetramethylhexane
cis-2,3-dimethyl-2-butene
4,4-di(2-butyl)nonane
3-methyl-1,4-pentadiene
1,2,3-trimethylcyclobutane
2,5-dichloro-2,5-difluoro-3-hexyne
trans-2-pentene
2,3-dinitro-1,3-butadiene
b) CH3-CH(CH3)-CH(C2H5)-CH2–CH2-CH2-CH3
c) CH2Br-CH(NO2)-CH2-CH2-CH3
d) CH3-CH2-CH(CH3)-C(CH3)2-CH(CH3)-CH3
CH3-CH-CH3
e) CH3-CH2-C(C2H5) 2-CH(CH3)-CH–CH2-CH2-CH3
CH3 CH3
f)
CH3-C = C–CH3
g) C = C(CH3)–CH3
CH3-CH-CH2-CH3
h) CH3-CH2--CH2–C–CH2-CH2–CH2-CH2-CH3
CH3-CH-CH2-CH3
CH3
i) CH3-CH2-C = C–CH2–CH3
j) CH2=CH–CH(CH3)–CH=CH2
CH3
k) CH2=CH–CH–CH2-CH3
n) CH3-CClF–Co
l) H3C
–CClF–CH3
CH3
m) CH2 – CH2
CH3
o) CH2=CH-C = C–CH=CH-CH3
NH2 NH2
CH3
p)
C=C
q) CH2=CH2-CCl3
r) CH2=C(NO2)–C(NO2)=CH2
C2H5
7.a) Draw and name the 5 different isomers of hexane b) Draw and name the 7 isomers of C3H4Cl2
a) CH3-CH2-CH2-CH2-CH2-CH3
n-hexane
b) CH3-CH(CH3)-CH2-CH2-CH3
2-methylpentane
c) CH3-CH2-CH(CH3)-CH2-CH3
3-methylpentane
d) CH3-CH(CH3)-CH(CH3)-CH3
2,3-dimethylbutane
e) CH3-C(CH3)2-CH2-CH3
2,2-dimethylbutane
7b)
1) 1,1-dichloropropene
3) 3,3-dichloropropene
5) 1,2-dichlorocyclopropane
7) 1,1-dichlorocyclopropane
2) 2,3-dichloropropene
4) trans-1,2-dichloropropene
6) cis-1,2-dichloropropene
8. Draw the structural diagram & name 2 different alkenes isomeric with cyclobutane
i) CH2=CH–CH2–CH3
1-butene
ii) CH3–CH=CH–CH3
2-butene
iii) CH2 = C – CH3
2-methylpropene
CH3
Group 2: CARBOHYDRATES - Composed of carbon chains where one or more carbons has been oxidized. These
oxygen atoms (and nitrogen atoms) make the carbon based molecule behave
differently the functional groups. Molecules that have the same groups of
Oxygens/Nitrogens all tend to behave similarly.
A) ALCOHOLS:
General formula R-OH where R = any group of carbons (pg 38-42-Nelson Chem 12)
NAME: name the group of carbons (R) then add the suffix "ol" instead of “e”
CH3OH  methanol
CH3–CH2–OH ethanol
CH3-CHOH-CH3
2-propanol
wood alcohol
Rubbing alcohol
grain alcohol -booze
CH2–CH2 –CH2
CH3-CH2-CH2–OH
1-propanol
(1° alcohol)
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CH3-CHOH-CH3
2-propanol
(2° alcohol)
OH OH OH
CH3-C(CH3)OH-CH3 2-methyl 2-propanol (3° alcohol)
1,2,3-propantriol  glycerol
9. Using the IUPAC rules name the following organic alcohols
a) CH3-CH2-CH2–OH
propanol
b) CH3-CHOH-CH3
2-propanol.
c) CH3-C(CH3)OH-CH3
2-methyl-2-propanol
d) CH3–CHOH–CH2CH3
e) CH3–C(CH3)2–CH2OH
2-butanol
2,2-dimethyl-propanol
f) CH2OH–CH2OH
1,2-ethandiol
10. Using the IUPAC rules draw the following organic alcohols
a) cyclobutanol
b) 2,3-dimethyl-2-hexanol
-OH
c) 4,4-dimethyl-1,2-pentandiol
CH3-COH-CH(CH3)-CH2
CH3
CH2OH-CHOH-CH2
CH2
C(CH3)2
CH3
CH3
11. i) Write the correct name for each alcohol & ii) Which alcohol is not an isomer of all the others ? & iii) Which alcohols are identical ?
a) CH3-C(CH3)2-CH2–OH
2,2-dimethyl-propanol
b) C2H5-C(CH3)2–OH
2-methyl-2-butanol.
c) C3H7-CHOH-CH3
2-pentanol
d) CH3-CH2-CH2-CH2-OH
butanol
e) C2H5-CH(C2H5)-OH
3-pentanol
f) C4H9-CH2-OH
1-pentanol
ident
g) CH3-CHOH-CH2-CH2-CH3
2-pentanol
ident
h) CH3-(CH2)3-CH2OH
1-pentanol
ident
ide
12. Draw the structure of the following benzene derivatives.
a) chlorobenzene
b) o-iodotoluene
c) 3-chlorophenol
d) m-nitrobenzaldehyde
e) 1,3,5-triethylbenzene
f) benzyl alcohol (C6H5CH2OH)
g) aminobenzene (aniline)
h) 1,4-dimethylbenzene (p-xylene) i) 2,4,6-trinitrotoluene
j) 1,3-dibromo-2-phenyl-2-pentene
k) 3,5-difluoro-4-isobutylbenzoic acid
l) 1-phenylethene (styrene)
m) 1,1-di(4-chlorophenyl)-2,2,2-trichloroethane
n) 1-phenyl-2-aminopropane ( benzedrine/speed)
13. Using the IUPAC rules name the following organic molecules each containing a functional group
a) CH3–CHOH–CH2CH3
b)
-OH
e) CH(OH)2-CCl3
F-
-F
d) CH3–C(CH3)2–CH2OH
O
f) C5H11–O–C4H9
g)
CH-CH3
CH3
c) CH2CHClCH2OH
h) CH3(CH2)2CHOHCH(C2H5)CH2OH
i) CH3CHBr–O–CH2CH2CH2Cl
j) CH2=CH-CH=CH-CH=CH-CH2–O–CH3
k) C3H7–O–CH2CH=CH–CHF-CH3
l)
-CH-CHO
CH3
m) CH3CH(CH3)–CH2CHO
p)
CH=C-CH2-CO-CH2-CH3
n) CH3CH2CH(C2H5)CH(CH3)CHO
o)
CH2-CO-CH2
q) CH3-CHF-CH2-CO-CH2-CH3
Br
r) CH2Br-CHBr-CH(C6H5)-CO-CH3
s) CH3-C(CH3)2-CH2-COOH
t) CH3CHFCH(CH3)CH2COOH u) HOOC–COOH v) H2N
COO-CH3 w) CH3-COO-I
x) CH3(CH2) 3–COO–(CH2) 3CH3
y) CH3-CH2-COO-CH2-CH(CH3)-CH2-CH3
z) C4H9–NH2
aa) C3H7–N(CH3)–C2H5
ab) CH(CH3)2–NH–CH2-CH2Cl
ac) CH3CH2CO–NH2
ad) CH3-CH2-CH2CO–NH–C5H11
ae) NH2CH2COOH (glycine)
13 a) 2-butanol
b) 2,3-difluorocyclopropanol
q) 5-fluoro-3-hexanone
e) 2,2,2-trichloro-1,1-ethandiol
r) 4,5-dibromo-3-phenyl-2-pentanone
s) 3,3-dimethylbutanoic acid
t) 4-fluoro-3-methylpentanoic acid
u) ethandioic acid
f) butylpentylether
v) methyl-3-aminobenzoate
g) phenylisopropylether
w) 3-iodocyclohexylethanoate
h) 2-ethyl-1,3-hexandiol
x) butylpentanoate
i) 1-bromoethyl-3-chloropropylether
y) 2-methylbutylpropanoate
j) 2,4,6-heptatrienylmethylether
z) butanamine or aminobutane
c) 2-chloro-3-cyclobutylpropanol
d) 2,2-dimethylpropanol
k) 4-fluoro-2-pentenylpropylether
aa) ethylmethylpropanamine
l) 2-cyclopentylpropanal
ab) 2-chloroethyl-2-propanamine
m) 3-methylbutanal
ac) propanamide
n) 3-ethyl-2-methylpentanal
ad) N-pentylbutanamide
ae) 2-aminoethanoic acid
o) 1,3-dicyclohexylpropanone
p) cis-2-cyclobutyl-1-(2bromophenyl)-1-hexen-4-one
- an amino acid for you biologists
14. Using the IUPAC rules draw the following organic molecules each containing a functional group
a) cyclopentanol
b) 3-isopropyl-2,3-dimethyl-2-hexanolc) 4,4-dimethyl-1,2-pentandiol
d) pentachlorophenol
e) 1,2,3-trichloro-4,5,6-trihydroxybenzene
f) 1-phenylethanol
g) dicyclobutylether
h) methyl-2-methylpentylether
i) methylphenylether
j) 2,4-difluoro-3,4-dimethylpentanal
k) 2-ethylhexanal
l) 4-hydroxy-3-methoxybenzaldehyde
m) 3-cyclopropyl-4-methyl-2-hexanone (vanillin)
n) 3-cyclopentenone
o) 4,5-dibromo-3-ethyl-2-heptanone
p) trichloroethanoic acid
q) 2-iodo-6-methyloctanoic acid
r) 2-hydroxypropanoic acid (lactic acid)
s) cis-butendioic acid
t) 3-butenoic acid
u) propyl-2-methylbutanoate
v) pentyl butanoate
w) 3-methylbutyl-3-methylbutanoate
x) ethyl-4-aminobenzoate (benzocaine)
y) 2-chloroethyl ethanoate
z) methyl-2-aminophenylmethanoate
aa) ethylbutanamine
ab) ethyl,propyl,pentanamine
ac) N,N-ethyl,butylpropanamide
ad) N,N-diethyl-metatoluamide (DEET)
ae) 2-aminopropanoic acid (alanine)
af) 2-amino-3-phenylpropanoic acid (phenylalanine)
ag) 2-hydroxy-1,2,3-propantricarboxylic acid (citric acid)
Reactions involving organic molecules
This section deals with the variety of chemical reactions that involve the organic molecules you have just learn to identify
1) They all combust- forming oxides ie C4H10 + 6.5 O2 → 4 CO2 + 5 H2O
or H2NC5H10COOH + 9¼ O2 → 6 CO2 + 6½ H2O + NO2
15.a) 3-ethyl-2-methylheptane + O2 (g)
b) 2,5-diammino-4-isopropylhexanoic + O2 (g)
a) C10H22 + 15.5 O2 → 10 CO2 + 11 H2O
b) (NH2)2C8H15COOH
+
15 O2 → 9 CO2 + 10 H2O + 2 NO2
2) The alkANEs (fully saturated) tend to undergo SUBSTITUTION reactions producing an alkyl halide ie
halogenation with Cl2 or Br2 etc (see pg 24 CHEM 12)
Energy
CH4 + Cl2 
 CH3Cl + HCl
Energy
C2H6 + Br2 
 C2H5Br + HBr
or
hf
hf
*The MECHANISM is“FREE RADICAL” (light sensitive). A “FREE RADICAL” is a high energy
unstable molecule because of an unpaired electron. ex: Cl. or .CH3
A)
Cl2 → 2 Cl.
initiation step
B) Cl. + CH4 → .CH3 + HCl
chain step 1
C) .CH3 + Cl2 → CH3Cl + Cl.
chain step 2
D)
2 Cl. → Cl2
termination step
Energy
CH4 + Cl2 
 CH3Cl + HCl
hf
overall reaction
**NOTE: Stability of the carbonyl free radicals is 3° > 2° > 1° . this means that if propane undergoes this
type of reaction the only product formed would be 2-chloropropane.
CH3– CH2– CH3 + Cl2 → CH3– CHCl – CH3 + HCl
16.(complete & name the product) a) butane + Br2 b) 2-methylbutane +Cl2 c) hexane + I2 d) 3-methylpentane + F2
1°
a)
2°
2°
1°
butane + Br2 → CH3-CHBr-CH2-CH3
+
HBr
2-bromobutane
1°
b)
3°
2°
1°
2-methylbutane + Cl2 → CH3-C(CH3)Cl-CH2-CH3
+
HCl
2-chloro-2-methylbutane
1°
c)
2°
2°
2°
2°
1°
hexane + I2 → CH3-CHI-CH2-CH2-CH2-CH3 +
→ CH3- CH2-CHI-CH2-CH2-CH3 +
HI
HI
50:50 mixture 2-iodohexane & 3-iodohexane
1°
2°
3°
2°
1°
d) 3-methylpentane + F2 → CH3-CH2-C(CH3)F-CH2-CH3 + HF
3-fluoro-3-methylpentane
3) The alkyl halides can undergo an elimination reaction forming an alkene (see pg 36 - CHEM 12)
CH3– CHCl – CH3 + OH- (a base) → CH2=CH– CH3 + H2O + Cl-
4) The alkENEs & alkYNEs (unsaturated) are much more reactive because of the π cloud of electrons on top of the
double bond and tend to undergo ADDITION reactions across this dble bond. (see pg 25 CHEM 12)
C3H6 + Br2 → C3H6Br2 halogenation
C3H6 + H2 → C3H8
hydrogenation
C3H6 + HCl → C3H7Cl hydrohalogenation
C3H6 + H2O → C3H7OH
hydration
*This MECHANISM is“ELECTROPHYLLIC” (hungry for electrons) – ΔG is very negative
H2C = CH2 + Cl:Cl  H2C -CH2 + Cl-  H2C-CH2 + Cl-  H2C -CH2
\ /
| +
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attacks the π cloud
Cl
Cl
Cl Cl
seeking the 2 electrons
**NOTE: Stability of the carbonium ion C+ is 3° > 2° > 1° . this means that if 1-propene undergoes this
type of reaction with a hydrogen halide like HCl the only product formed would be 2-chloropropane as
the 2° carbon(in the middle) would become C+ and that is where the negative Cl- will attach. This is
known as Markovnikov’s Rule (the H attaches to the carbon that already has the most H’s)
CH2=CH–CH3 + HCl → CH3– CHCl – CH3
17. i) Do practice exercise #1 (pg 27) , understanding concepts # 2,3,4,5 & 6 ( pg 31)
ii) (complete & name the product)
#1(pg 27)
#1(pg 27)
#1(pg 27)
#1(pg 27)
a) cyclohexene + Cl2
c) 2,2-dimethyl-4-octene + F2
b) 3-methyl-3-hexene +HBr
d) 2-methyl-3-pentene + HI
CH3-CH=C(C2H5)-CH2-CH3 + H2 → CH3-CHHCH(C2H5)-CH2-CH3
3-ethyl-2-pentene
3-ethylpentane
CH3-CH=C(CH3)-CH2-CH3 + HBr → CH3-CHHCBr(CH3)-CH2-CH3
3-methyl-2-pentene
3-bromo 3-methylpentane
CH3CH2CH(C2H5)CH=CH2 + H2O → CH3CH2CH(C2H5)CHOHCH3
3-ethyl-1-pentene
3-ethyl-2-pentanol
cyclohexene
+
Cl2
→ 1,2-dichlorocyclohexane