Date post: | 02-Apr-2018 |
Category: |
Documents |
Upload: | pradipta-debnath |
View: | 318 times |
Download: | 4 times |
of 48
7/27/2019 CHEM 1152 - Chem Workbook
1/48
7/27/2019 CHEM 1152 - Chem Workbook
2/48
2SCH4U0 CHEMISTRY Workbook
Page 2 of48
7/27/2019 CHEM 1152 - Chem Workbook
3/48
3SCH4U0 CHEMISTRY Workbook
Page 3 of48
7/27/2019 CHEM 1152 - Chem Workbook
4/48
4SCH4U0 CHEMISTRY Workbook
Page 4 of48
7/27/2019 CHEM 1152 - Chem Workbook
5/48
5SCH4U0 CHEMISTRY Workbook
PREPARATION OF ALKANES
1. Hydrogenation of alkenesH2
Pt
2. Hydrogenation of alkynes
H2
PtCH CH CH3 CH3
2
REACTION OF ALKANES
1. Halogenation
CH3 H + X2light
CH3 X
Reactivity: X2: Cl2 > Br2
H: 3>2>1>CH3-H
PREPARATION OF ALKYL HALIDES
1. From Alcohols
CH3 OH CH3 XHX or PX3
X = Cl, Br, or I
2. Halogenation of certain hydrocarbons
CH3 H + X2light
CH3 X
Reactivity: X2: Cl2 > Br2
H: 3>2>1>CH3-H
3. Addition of hydrogen halides to akenes
CH2 CH2HX
X H
H
H
H
H
H usually attaches to least substituted carbon atom in double bond (Markovnikov addition)
4. Addition of halogens to alkenes or alkynes
CH2 CH2X X
HH
H
H
X2CH CH
X22XX
X X
HH
Page 5 of48
7/27/2019 CHEM 1152 - Chem Workbook
6/48
6SCH4U0 CHEMISTRY Workbook
trans-addition across double bonds in rings
5. Halide exchange
CH3 X + NaI (or NaBr) CH3 I(or Br) + NaClacetone
X=Cl or Br
1>>2
NaCl ppts from acetone and drive the reaction to completion
REACTION OF ALKYL HALIDES
1. Nucleophile Substitution
CH3 X + OH- CH3 OH alcohol
+ H2O CH3 OH alcohol
+ C R CH3 R alkyne
+ R M CH3 R alkane couplingM = Li or Mg
+ I- CH3 I alkyl iodide
+ RCOO- CH3O
ORester
+ NH3 CH3 NH2 primary amineNH2R
NHR'R"
secondary amine
tertiary amine
2. Dehydrohalogenation: Elimation
H X
H
H
H
Hbase
CH2 CH2
3. Preparation of Grignard Reagent
CH3 X Mg+ether
CH3 MgX
PREPARATION OF ALCOHOLS
1. Hydration
CH2 CH2 + H2OOHH
H
H
H
H
Markovnikov addition
2. Grignard synthesis
CH3 CH3
O
+ R-Mg-X ether
CH3
CH3
R
OMgX H2O
R
CH3
CH3
OH
Page 6 of48
7/27/2019 CHEM 1152 - Chem Workbook
7/48
7SCH4U0 CHEMISTRY Workbook
Ketones or aldehydes
3. Hydrolysis of alkyl halides
CH3 X + OH- CH3 OH + X-
Usually requires a silver salt so can be very expensive
4. Reduction of ketones and aldehydes
CH3 H
OH2, Pt
CH3 H
OHH
CH3 CH3
OH2, Pt
CH3 CH3
OH
H
5. Hydrolysis of alkenes
CH2 CH2
KMnO4
OHOH
HHH
Hcis-addition
6. Hydrolysis of Esters
CH3
O
OR
H+
or
NaOH, H2O CH3
O
OH
+ OH R
REACTION OF ALCOHOLS
1. Reaction with hydrogen halides
CH3 OH + HX CH3 X
2. Dehydration
OHH
H
H
H
HH
+
CH2 CH2heat
More substituted alkenes is favoured: 3>2>1
3. Ester Formation
CH3OH
O
+ R OH H+
CH3
O
OR
4. Oxidation
Page 7 of48
7/27/2019 CHEM 1152 - Chem Workbook
8/48
8SCH4U0 CHEMISTRY Workbook
CH3 OHPCC, CH2Cl2
CH3H
O
CH3 CH3
OH
H
KMnO4
CH3
CH3
O
excess, KMnO4
CH3 OH
O
PREPARATION OF ETHERS
1. Condensation
CH3 OH OH R+ CH3 OR
PREPARATION OF ALKENES
1. Reduction of Alkynes
CH CH
H21
PtCH2 CH2
REACTION OF ALKENES
1. Addition of hydrogen. Catalytic hydrogenation
CH2 CH2
H2, Pt
CH3 CH3
2. Addition of halogens
CH2 CH2
X2
X X
HHH
H
3. addition of hydrogen halides
CH3
CH2
HXCH3
CH3
X
Markovnikov addition
4. addition of water
CH3
CH2
OH2CH3
CH3
OH
H+
Markovnikovs addition
5. Hydroxylation
CH2 CH2
KMnO4
OH OH
HHH
H
PREPARATION OF ALKYNES
Page 8 of48
7/27/2019 CHEM 1152 - Chem Workbook
9/48
9SCH4U0 CHEMISTRY Workbook
1. Reaction of metal acetylides with primary alkyl halides
CH3
CH
Na
CH3
C- Na+
R X
R must be primary
CH3
R
REACTION OF ALKYNES
1. Addition of hydrogenCH CH
1 H2, PtCH2 CH2
1 H2, PtCH3 CH3
2. Addition of halogens
CH CH2 X2
X
X X
XH H
3. Addition of hydrogen halides
CHCH3
2 HX
CH3
X
H
X
H Markovnikov Addition
4. Formation of metal acetylides
CH3
CH
Na
CH3
C- Na+
PREPARATION OF ALDEHYDES
1. Oxidation of primary alcohols
OH
CH3
KMnO4CH3
O
H
PREPARATION OF KETONES
1. Oxidation of secondary alcohols
CH3
CH3
OHKMnO4
CH3CH3
O
REACTION OF ALDEHYDES and KETONES
1. Oxidation of aldehydes carboxylic acid
CH3
O
H
KMnO4
CH3
O
OH
2. Reduction of aldehydes 1 alcohols
Page 9 of48
7/27/2019 CHEM 1152 - Chem Workbook
10/48
10SCH4U0 CHEMISTRY Workbook
CH3
O
H
H2, Pt
CH3
OH
H
H
3. Reduction of ketones 2 alcohol
CH3 CH3
O
H2, PtCH
3 CH3
OH H
PREPARATION OF CARBOXYLIC ACIDS
1. Oxidation of primary alcohols
OHCH3
KMnO4, excessCH3
O
OH
2. Hydrolysis of Esters
CH3
O
OR
H+
or
NaOH, H2O CH3
O
OH + OHR
REACTIONS OF CARBOXYLIC ACIDS
1. Acidity. Salt Formation
CH3 OH
O+
NaOHCH3
O-
O
Na+
2. Conversion into Ester
CH3OH
O
+ R OH H+
CH3
O
OR
3. Conversion into Amide
CH3OH
O
CH3NH2+ CH3 NH
O
CH3
REACTION OF BENZENE
HNO3
H2SO4
NO2CH3CH3
Cl
AlCl3
Page 10 of48
7/27/2019 CHEM 1152 - Chem Workbook
11/48
11SCH4U0 CHEMISTRY Workbook
Intramolecular and Intermolecular Forces
Intramolecular forces
Forces of electrostatic attraction within a molecule
Occur between the nuclei of the atoms and their electrons making up the molecule (i.e. covalent bonds)
Must be broken by chemical means
Form new substances when broken
Intermolecular forces
Forces of attraction between two molecules (i.e. London dispersion forces, dipole dipole interactions orhydrogen bonds)
These forces are much weaker than Intramolecular forces or bonds and are much easier to break
Physical changes ( changes of state) break or weaken these forces
Do not form new substances when broken
These forces affect the melting and boiling points of substances, the capillary action and surface tension, aswell as the volatility and solubility of substances
Types of Intermolecular forces
London dispersion forces
These forces are based on the simultaneous attraction of the electrons of one molecule by the positive nucleiof neighbouring molecules
The strength of the force is directly related to the number of electrons and protons in a given molecule
The greater the number of electrons and protons the greater the forceDipole - Dipole Interactions
Occur between polar molecules having dipoles
Molecules with dipoles are characterized by oppositely charged ends that are due to an unequal distribution ofcharge on the molecule
The polarity of a molecule is determined by both the polarity of the Intramolecular bond and the shape of themolecule
These forces are based on the simultaneous attraction of the electrons of one dipole by the dipoles ofneighbouring molecules
The strength of the force is related to the polarity of the given moleculeHydrogen Bonds
These forces are a type of dipole dipole interaction
Occur between Hydrogen atoms in one molecule and highly electronegative atoms [F, O, N, and S, P] where
there are usually unshared pairs of electrons present Hydrogen bond are the strongest of the Intramolecular forces and are about 1/10 the strength of a covalent
bond
Polarity and Boiling Point:
The polarity of the molecules determines the forces of attraction between the molecules in the liquid
state. Polar molecules are attracted by the opposite charge effect (the positive end of one molecule is
Page 11 of48
7/27/2019 CHEM 1152 - Chem Workbook
12/48
12SCH4U0 CHEMISTRY Workbook
attracted to the negative end of another molecule. Molecules have different degrees of polarity asdetermined by the functional group present.
Principle: The greater the forces of attraction the higher the boiling point or the greater the
polarity the higher the boiling point.
Molecules that are isoelectronic have the same strength of London dispersion forces
More polar molecules have stronger dipole dipole interaction and higher melting and boiling points The greater the number of electrons per molecule, the stronger the London forces and hence the higher
the melting and boiling point
Polarity Ranking of the Functional Groups:(most polar first)
Amide > Acid > Alcohol > Ketone ~ Aldehyde > Amine > Ester > Ether > Alkane
HW: Review of INTERMOLECULAR FORCES
2-13 For each of the following:
1. Record EN above each element2. EN difference predict type bond (polar covalent vs. non-polar covalent)3. SHOW presence of Dipole MOMENT (if any) Example:
H
H
Cl
Cl
H
H
H
F
F
F
F
F
H
O CH32.2
3.44 2.55
H
O
CH3 H
N
H
H
N
CH3CH3
CH3
HH
HCl
B
H
HH
Be ClCl
N+
H
H
H
H
Rank the following compounds in order of increasing boiling points. Explain the reason.
Page 12 of48
7/27/2019 CHEM 1152 - Chem Workbook
13/48
13SCH4U0 CHEMISTRY Workbook
CH3CH3
octane
CH3
CH3
CH3
CH3
CH3OH
butan-1-ol
2,3-dimethylbutane
CH3
CH3
OH
CH3
2-methylbutan-2-ol
2-16 For each pair of compounds circle the compound you expect to have the higher
boiling point. Explain your reasoning.
a) (CH3)3C-C(CH3)3 and (CH3)2CH-CH2CH2-CH(CH3)2
b) CH3(CH2)6CH3and CH3(CH2)5CH2OH
c) HOCH2-(CH2)4-CH2OH and (CH3)3CCH(OH)CH3
d) (CH3CH2CH2)2NH and (CH3CH2)3N
CH3
CH3
CH3
CH3
CH3CH3
CH3
CH3H
CH3
CH3
H
H
H
HH
CH3
H
HH
CH3OH
HH
OHOH
HH
H H
CH3
CH3CH3
H OH
CH3CH3
N
CH3
H
CH3
N
CH3
CH3
a)b)
c)
d)
2-17 Circle the member of each pair that is more soluble in water. Show the molecular
Page 13 of48
ANSWER
7/27/2019 CHEM 1152 - Chem Workbook
14/48
14SCH4U0 CHEMISTRY Workbook
representation
a) CH3CH2-O-CH2CH3 or CH3CH2CH2CH2CH3
b) CH3CH2NHCH3 or CH3CH2CH2CH3
c) CH3CH2OH or CH3CH2CH2CH2OH
CH3O CH3
CH3CH3
a)
CH3N
CH3
H
CH3 CH3
b)
CH3OH
CH3
OH
HH
c)
Page 14 of48
7/27/2019 CHEM 1152 - Chem Workbook
15/48
15SCH4U0 CHEMISTRY Workbook
Page 15 of48
ACTIVITY 1.2 THOUGHT LAB
7/27/2019 CHEM 1152 - Chem Workbook
16/48
16SCH4U0 CHEMISTRY Workbook
Page 16 of48
7/27/2019 CHEM 1152 - Chem Workbook
17/48
17SCH4U0 CHEMISTRY Workbook
Name Number of C atoms Molecular Formula
Methane 1 CH4
Ethane 2 C2H6
Propane 3 C3H8
Butane 4 C4H10
Pentane 5 C5H12
Hexane 6 C6H14
Heptane 7 C7H16
Octane 8 C8H18
Nonane 9 C9H20
Decane 10 C10H22
Naming ORGANIC COMPOUNDS Find the longest continuous carbon chain. Determine the root name for thisparent chain. In cyclic compounds, the ring is
usually considered the parent chain, unless it isattached to a longer chain of carbons; indicate a ring with the prefix cyclobefore the rootname. (When there are two longest chains of equal length, use the chain with the greater numberofsubstituents.).
Number the chain in the direction such that the position number of the firstsubstituent is the smaller number. If the firstsubstituents from either end have the same number,then number so that the second substituent has the smaller number, etc.
Determine the name and position number of each substituent. (A substituent ona nitrogen is designated with an N insteadof a number)
Indicate the number of identical groups by the prefixes di, tri, tetra, etc.
Place the position numbers and names of the substituent groups, in alphabetical order, before the root name. Inalphabetizing, ignore prefixes likesec-, tert-, di, tri, etc., butinclude iso and cyclo. Always include a position number foreach substituent, regardless ofredundancies.
Page 17 of48
7/27/2019 CHEM 1152 - Chem Workbook
18/48
18SCH4U0 CHEMISTRY Workbook
Worksheet #2
Page 18 of48
7/27/2019 CHEM 1152 - Chem Workbook
19/48
19SCH4U0 CHEMISTRY Workbook
Worksheet #3 - QUESTIONS: naming alkanes and cycloalkanesPractice Problems: name the following alkenes from their condensed structural formulas.
Page 19 of48
7/27/2019 CHEM 1152 - Chem Workbook
20/48
20SCH4U0 CHEMISTRY Workbook
Page 20 of48
STRUCTURE NAME STRUCTURE NAME
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
3-ethyl-3,4-
dimethylhexane
Hexane
3-ethyl-2,5-
dimethylheptane
3-methyl-2-
isopropyloctane
4-tert-butyl-3,8-
dimethyldecane
2,7-dimethyl-4,5-
dipropyloctane
CH3 CH3
CH3
CH3
CH3
1-isopropyl-3-
methylcyclopentane
CH3
CH3
CH3 1-ethyl-2,4-
dimethylcyclohexane
1-chloro-3-
ethylcyclooctane
cyclopropylcyclohexane
2,3,4-trimethylpentane 3,4-dichloro-2-
7/27/2019 CHEM 1152 - Chem Workbook
21/48
21SCH4U0 CHEMISTRY Workbook
Worksheet #4 - naming alkenes, cycloalkenes, alkynesNaming Alkenes and Alkynes The naming of alkenes is very similar to the naming of alkanes, with two exceptions.
In alkenes the double bonds take precedence over the substituted groups
The chain is numbered so that the double bonds have the lowest location numbers possible. If the double
bonds do not indicate a preferred numbering direction, look then to substituted atom
If more than one double bond is present, give the position of each and use one of the suffixes diene,-triene, and so on
For a cycloalkene, the double bond must be numbered 1,2
Note the double bond must be included in your longest chain.
Because of restricted rotation about a C=C double bond, groups on adjacent carbons are eithercis or
trans to each other
The cis-trans system: configuration is determined by the orientation of atoms of the main chain
We use the terms cis and trans to distinguish between alkenes which have identical groups on either side
of the double bond
NOTE: (alkene and alkyne) are considered to have equal priority: in a moleculewith both a double and a triple bond, whichever is closer to the end of the chaindetermines the direction of numbering. In the case where each would have the sameposition number, the double bond takes the lower number. In the name, ene comes
before yne because of alphabetization.
Page 21 of48
7/27/2019 CHEM 1152 - Chem Workbook
22/48
22SCH4U0 CHEMISTRY Workbook
Page 22 of48
STRUCTURE NAME STRUCTURE NAMECH3
CH2 CH3CH2
CH3
CH3
CH3
CH
CH3CH3
CH3
CH3
CH3
CH3
CH3
CH2
CH3
CH3
CH3
CH3
CH3
CH3 CH3
CH3CH3
CH3
Cl
CH3
CH3CH3
CH3 CH3
4-ethylcyclopentene CH3
CH3
CH3
CH3
CH3 2-isopropyl-4-
methylpenta-1,3-diene
cis-2,4,6-octatriene 2,5-dimethylhex-3-yne
1,3-dimethylcyclopenta-
1,3-diene
2-methylpent-1-ene
3,4-dimethylpent-1-yne
CH3
CH3
CH3
CH3
2,4-methylhex-2-ene 4-chloro-1-
cyclopentyl-2-
methyl-1,3-
cycloheptadiene4-methylhept-1-ene 2,4-methylhex-2-ene
7/27/2019 CHEM 1152 - Chem Workbook
23/48
23SCH4U0 CHEMISTRY Workbook
Page 23 of48
7/27/2019 CHEM 1152 - Chem Workbook
24/48
24SCH4U0 CHEMISTRY Workbook
Organic Chemistry Nomenclature Project
Hydrocarbons
CH3 CH3
CH3CH3
cyclopentane
1)____________________________ 2)__________________________________
CH3CH3CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
3)____________________________ 4)__________________________________
5-butyl-3,3,7,7-tetramethylnonane 2,3-dimethylbutane
5)____________________________ 6)__________________________________
dimethylcyclopropyne 5-cyclopropyl-trans-3-heptene
7)____________________________ 8)__________________________________
CH3
CH3
4-butyl-2-ethyl-1-pentyl-1,4-cycloheptadiene
9)____________________________ 10)__________________________________
Page 24 of48
7/27/2019 CHEM 1152 - Chem Workbook
25/48
25SCH4U0 CHEMISTRY Workbook
Name: Page 2
Page 25 of48
7/27/2019 CHEM 1152 - Chem Workbook
26/48
26SCH4U0 CHEMISTRY Workbook
Organic Chemistry Nomenclature Project
Aromatics
CH3CH3
3-phenylpentane
1)____________________________ 2)__________________________________
methyldiphenylmethane p cyclopropylethylbenzene3)____________________________ 4)__________________________________
CH3
CH3
5-butyl-3-ethyl-7-phenylnonane
5)____________________________ 6)__________________________________
NO2O2N
CH3
CH3 7)____________________________ 8)__________________________________
CH3CH
3
2,4-dimethyl-1-propylbenzene
9)____________________________ 10)__________________________________
Name: Page 3
Page 26 of48
7/27/2019 CHEM 1152 - Chem Workbook
27/48
27SCH4U0 CHEMISTRY Workbook
Organic Chemistry Nomenclature Project
Halides
CH3
Br
Cl
F
CH3 o 1,3-dichlorobenzene
1)____________________________ 2)__________________________________
3-bromo-2,4,4-trifluoro-6-iodoheptane 1,2,3,4,8-pentaiodo-1,3,5-cyclooctatriene3)____________________________ 4)__________________________________
Br
Br
CH3 CH3
NO2
Cl
5)____________________________ 6)__________________________________
Cl
FBr
F
6-chloro-1,1,1-trifluoro-2-phenyl-3-heptyne
7)____________________________ 8)__________________________________
ClF
I
Br
CH3
4,7,9-tribromo-3-fluoro-6,8-dimethyl-cis-2-decene
9)____________________________ 10)__________________________________
Page 27 of48
7/27/2019 CHEM 1152 - Chem Workbook
28/48
28SCH4U0 CHEMISTRY Workbook
Worksheet #8: REACTIONS OF HYDROCARBONS
1)
2) PREDICT PRODUCTS:
ADVANCED:
Page 28 of48
7/27/2019 CHEM 1152 - Chem Workbook
29/48
29SCH4U0 CHEMISTRY Workbook
ADVANCED
ADVANCED
3) For each of following reactions use structural diagram to show all reactants and products. Be sure to include al
names, reaction conditions and catalysts.a. 3-ethyl-2-heptene reacts with water in the presence of acidb. 2-methyl-2-pentene reacts with hydrochloric acidc. tertiary-butane reacts with bromine gas in the presence of lightd. halogenation of propanee. bromomethane is purged with NaIf. hydrogenation of 1,3-dimethylcyclopenta-1,3-dieneg. Hydration of 2-isopropyl-4-methylpenta-1,3-dieneh. Complete hydrohalogenation of 2,5-dimethylhex-3-ynei. Combustion (extreme oxidation) ofcis-2,4,6-octatrienej. Complete halogenation of 3-methylhept-1-ynek. Octane burns in oxygenl. 2-methylcyclohex-1-ene reacts with hydrobromic acid
4) Predict the products of each of the following reactions. (Name the reactants and products).
5) Synthesis the following molecules.
5)Explainwhy it isthat acidcatalyzedaddition ofwater to 1-
methylcyclobutene gives 1-methylcyclobutanol and not 2-methylcyclobutanol.
Page 29 of48
7/27/2019 CHEM 1152 - Chem Workbook
30/48
30SCH4U0 CHEMISTRY Workbook
Worksheet #9: Naming, Reactions, synthesis of Alcohols and Ethers
1. Indicate whether the following alcohols are primary, secondary, or tertiary.
a)CH3
OH
b)
CH3
CH3
CH3
OH
c)
CH3
OH
d)
OH e)2-methyl-2-pentanol
f)CH3
OH
2. Diethyl ether (commonly called ether) is a structural isomer of 1-butanol. Whichcompound would you expect to have the higher boiling point? Explain your answer.
3. For each of the following pairs of compounds give a simple, visual chemical test you coulduse to distinguish between the two molecules. Give chemical reagents and theobservation you would make.
a)CH3 OH
and
CH3 O
CH3
b)CH3
OH and
CH3
CH3
CH3
OH
c)
OH
and OH
4) Give the products of the following reactions. Use N.R. if no reaction occurs
a)CH3
OHHCl
b)CH3
CH3
OH
+ K2Cr2O7H+
c)CH3
OH+conc.H2SO4
Page 30 of48
7/27/2019 CHEM 1152 - Chem Workbook
31/48
31SCH4U0 CHEMISTRY Workbook
e)+CH3O
-Na+ CH3Br
f)CH3 OH + KMnO4 (excess)
g)+
OH
PCC/CH2Cl
2
H+
h)CH3
CH3
I
+ dilute NaOH25C
5) For each of the following, provide the reagent(s) required to convert the starting
compounds into the products. Some of these conversions may required more than a single
reaction step.
a)
CH3OH
CH3
b)CH3 CH3
CH3 CH3
O
2 steps
c)CH3
BrCH3
OH
d)
OH
2 steps
e)
CH3 OHCH3
O
OH
f)
BrO
2 steps
Name or draw structures for the following compounds.
(e) isobutyl alcohol(f) 2-buten-1-ol(g) 2,4-hexanediol(h) cis-3-ethylcyclobutanol
Name: Page B4Page 31 of48
7/27/2019 CHEM 1152 - Chem Workbook
32/48
32SCH4U0 CHEMISTRY Workbook
Organic Chemistry Nomenclature Project
Alcohols
OH
CH3CH3
2-bromo-3,4-dihydroxypentane
1)____________________________ 2)__________________________________
OH
2-hydroxy-1,3-cyclobutadiene
3)____________________________ 4)__________________________________
ICl Cl
OHOHCl
CH3CH3
4-hydroxy-trans-2-hexane
5)____________________________ 6)__________________________________
OH
OH
p1,2-dihydroxybenzene
7)____________________________ 8)__________________________________
OH
CH3
CH3
CH3
CH3
CH3
3,4,4-triphenyl-2-butanol
9)____________________________ 10)__________________________________
Page 32 of48
7/27/2019 CHEM 1152 - Chem Workbook
33/48
33SCH4U0 CHEMISTRY Workbook
Name: Page B5
Organic Chemistry Nomenclature Project
Ethers
CH3 O
CH3
4-methoxy-2-pentyne
1)____________________________ 2)__________________________________
O
OH
CH3
2-chloroxypropane3)____________________________ 4)__________________________________
CH3 O
CH3 O O
dipropylether
5)____________________________ 6)__________________________________
O
CH3
CH3
2,6-dibromo-5-fluoroxy-4-methyl-cis-2-heptene
7)____________________________ 8)__________________________________
O
3-iodo-3-methoxy-2-phenyl-1-propanol
9)____________________________ 10)__________________________________
Page 33 of48
7/27/2019 CHEM 1152 - Chem Workbook
34/48
34SCH4U0 CHEMISTRY Workbook
Worksheet #10
Naming, Synthesis, Reactions of Aldehydes, Ketones, Carboxylic
Acids
Page 34 of48
7/27/2019 CHEM 1152 - Chem Workbook
35/48
35SCH4U0 CHEMISTRY Workbook
PRACTICE: Name the following compounds
1.
2.
3
4
5
6
7
8
9
10Give the products of the following reactions. Use N.R. if no reaction occurs.
a)
CH3O
H
H2
Pt
Page 35 of48
7/27/2019 CHEM 1152 - Chem Workbook
36/48
36SCH4U0 CHEMISTRY Workbook
b)
CH3O
H
KMnO4, H+
c)
CH3
CH
CH3
Na+
+
O
ClH
d) CH3CH3
O K2Cr
2O
7, H+
e) CH3 OH
O
OH2+
f)CH3
OH
O
+Na OH
g)CH3
O
H
K2Cr
2O
7, H+
Page 36 of48
7/27/2019 CHEM 1152 - Chem Workbook
37/48
37SCH4U0 CHEMISTRY Workbook
Name: Page B6
Organic Chemistry Nomenclature Project
Aldehydes and Ketones
CH3
O
CH3 propanal
1)____________________________ 2)__________________________________
O
CH3
CH3
CH3
2,4-dichlorobenzaldehyde
3)____________________________ 4)__________________________________
CH3
OO
CH3
CH3
4-cyclobutyl-trans-2-pentenal
5)_____________________________ 6)__________________________________
O
CH2
2,6-difluoro-3,3,5-trihydroxycyclooctanone
7)___________________________ 8)__________________________________
Page 37 of48
7/27/2019 CHEM 1152 - Chem Workbook
38/48
38SCH4U0 CHEMISTRY Workbook
pent-4-yn-2-one 4-chloroxy-1,2-dibromo-2-methyl-4-nitro-butanal
9)____________________________ 10)__________________________________
Name: Page B7
Organic Chemistry Nomenclature ProjectCarboxylic Acids
OHOH
O
OH
CH3
pentanoic acid
1)____________________________ 2)__________________________________
CH3
CH3
CH3
CH3
CH3
O
OHCH3
2,5-dimethyl-cis-3-heptenoic acid
3)____________________________ 4)__________________________________
CH3
O
OH
4-cyclopropyl-2-nitro-3-butynoic acid
5)____________________________ 6)__________________________________
CHO
OH
CH33-methoxybenzoic acid
7)____________________________ 8)__________________________________
I
I
O
CH3
O
OH
CH3
Page 38 of48
7/27/2019 CHEM 1152 - Chem Workbook
39/48
39SCH4U0 CHEMISTRY Workbook
butanedioic acid
9)____________________________ 10)__________________________________
Page 39 of48
7/27/2019 CHEM 1152 - Chem Workbook
40/48
40SCH4U0 CHEMISTRY Workbook
Page 40 of48
7/27/2019 CHEM 1152 - Chem Workbook
41/48
41SCH4U0 CHEMISTRY Workbook
Name: Page B8
Organic Chemistry Nomenclature Project
Esters
CH3
O
O
CH3
propyl butanoate
1)____________________________ 2)__________________________________
Page 41 of48
7/27/2019 CHEM 1152 - Chem Workbook
42/48
42SCH4U0 CHEMISTRY Workbook
phenyl hexanoate dichloromethyl 2-ethoxypropanoate
3)____________________________ 4)__________________________________
CH3
Br O
O
CH3
CH3
methyl acetate
5)____________________________ 6)__________________________________
2-phenyl-trans-3-pentenyl 2-hydroxybenzoate 2-nitrocyclohexyl ethanoate
7)____________________________ 8)__________________________________
CH3
CH3
O
O CH3 O
O
O
CH3CH3
9)____________________________ 10)__________________________________
Page 42 of48
7/27/2019 CHEM 1152 - Chem Workbook
43/48
43SCH4U0 CHEMISTRY Workbook
Name: Page B9
Organic Chemistry Nomenclature Project
Amines
CH3
CH3
NCH3
ethylmethylamine
1)____________________________ 2)__________________________________
OHNH
CH3
CH33-amino-4,5,6,7-tetramethylnonane
3)____________________________ 4)__________________________________
2,3-diamino-N3-chloro-N2-methylpentane cyclopentyl 2-amino-N-methylbutanoate
5)____________________________ 6)__________________________________
N
5-aminohex-1-yn-3-one
7)____________________________ 8)__________________________________
CH3
OH
NH2
NH
CH3
N,N-dimethylaniline9)____________________________ 10)_________________________________
Page 43 of48
7/27/2019 CHEM 1152 - Chem Workbook
44/48
44SCH4U0 CHEMISTRY Workbook
Name: Page B10
Organic Chemistry Nomenclature Project
Amides
CH3O
NH2
2-bromo-N-ethylpropanamide
1)____________________________ 2)__________________________________
CH3
NH2
F
CH3 O
N
3-cyclopropyloxy-N-ethyl-N,6-dimethylheptanamide
3)____________________________ 4)__________________________________
NH
CH3 O
NO2
N-iodo-N-methyl-3-pentynamide 5)____________________________ 6)__________________________________
OBrBr
CH3
O NH2 CH3
N-cycloheptyl-N-phenylacetamide
7)____________________________ 8)__________________________________
CH3
OH
CH3
O
CH3O
CH3 O
NH2
N,N-dihydroxybenzamide
9)____________________________ 10)__________________________________
Page 44 of48
7/27/2019 CHEM 1152 - Chem Workbook
45/48
45SCH4U0 CHEMISTRY Workbook
Page 45 of48
Worksheet #11
7/27/2019 CHEM 1152 - Chem Workbook
46/48
46SCH4U0 CHEMISTRY Workbook
Page 46 of48
7/27/2019 CHEM 1152 - Chem Workbook
47/48
47SCH4U0 CHEMISTRY Workbook
Worksheet #12 REVIEW
1. Write structural formulas for all organic compounds. State the type of reaction. Complete and balance the reaction. Name the
products.
a) propene + hydrogen
b) cyclohexane + chlorine
c) benzene + iodine
d) ethanol + butanoic acid
e) 2-pentene + bromine
f) ethene + water
g) chloroethane + sodium hydroxide
h) propene + bromine
i) chlorobenzene + chlorine
j) ethanol + hexanoic acid
k) 3-pentanol + oxygen
l) propyne + (2 mol) iodine
m) cyclohexene + water
n) ethoxyhexane + oxygen
o) polymerization of chloroethene
p) polymerization of propene
2. Account for the variation in boiling points among the following two carbon molecules:
ethane -88.6C chloroethane 12.2C
ethanol 78.5C ethanoic acid 117.9C
3. Draw structural formulas for each of the following molecules. Predict and explain the order of their boiling points
from highest to lowest.
a) CH3F b) C2H6 c) CH3OH d) C2H4
4. Given one of the starting materials and end product for each of the following reactions, show all reactants, reaction
conditions in brackets (where known) and products.
1. fluoroethane from ethanol
2. 3-methylpentane from 3-methyl-3-pentanol
3. acetone from propene
4. acetic acid from chloroethane
5. 2-iodopropane from acetone
6. 1-butanol reacts in the presence of concentrated sulfuric acid
7. ethyl ethanoate from ethane
8. isopropylbenzene from benzene
Page 47 of48
7/27/2019 CHEM 1152 - Chem Workbook
48/48
48SCH4U0 CHEMISTRY Workbook
5. Draw the following hydrocarbons. Make sure you know how to do line diagrams,
condensed formulas and structural formulas.
1. dichloromethane 2. 3,5-dichloro-4-cyclobutylheptane
3. cis-2,4,6-octatriene 4. 4-chloro-1-cyclopentyl-2-methyl-1,3-
cycloheptadiene
5. cyclohexylcyclohexane 6. 3-ethyl-5,5-diisopropyl-2-methyloctane
7. 2-methyl-4nitroocta-2-ene-5-yne 8. 5-chloro-3-ethyl-1-nitro-1,4-cyclooctadiene
9. trans-2,3-dichloro-6-isopropyl-4,5,7-trimethyl-2,4,6-decatriene
10. 1,2-dibromo-3,8-dichloro-5-ethyl-4-nitrooctacis-1-trans-3,7-triene-5-yne
Name the following hydrocarbons.
3. 4.
5. 6.
7. 8.
Cl Cl
H3C
HC
CH
HC
CH
CH3
CH3CH2C(CH3)2CH2CH3CH3(CH2)6CHCH2
Cl NH2
C C C C C C C
H
Cl
H
Cl Cl
H
H
H
HH
Br