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SCH4U0

CHEMISTRY Workbook

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SCH4U0

CHEMISTRY Workbook

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SCH4U0

CHEMISTRY Workbook

PREPARATION OF ALKANES 1. Hydrogenation of alkenes

H2

Pt

2. Hydrogenation of alkynes
2 H2
HC CH

Pt

H3C

CH3

REACTION OF ALKANES 1. Halogenation

H3C H

X2

light

H3C

Reactivity: X2: Cl 2 > Br2 H: 3>2>1>CH3-H

PREPARATION OF ALKYL HALIDES 1. From Alcohols

H3C OH
HX or PX3

H3C

X = Cl, Br, or I

2. Halogenation of certain hydrocarbons

H3C H

X2

light

H3C

Reactivity: X2: Cl2 > Br2 H: 3>2>1>CH3-H

3. Addition of hydrogen halides to akenes

H2C CH2 HX

H H X H

H H

H usually attaches to least substituted carbon atom in double bond (Markovnikov addition)

4. Addition of halogens to alkenes or alkynes

H2C CH2 X2 H H H X X HC CH H

2 X2

X H X

X H X

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SCH4U0 trans-addition across double bonds in rings 5. Halide exchange

H3C X

CHEMISTRY Workbook

acetone NaI (or NaBr) H3C I(or Br)

NaCl

X=Cl or Br

1>>2

NaCl ppts from acetone and drive the reaction to completion REACTION OF ALKYL HALIDES 1. Nucleophile Substitution
H3C X

+ + + + + + +

OHH 2O C R M R

H3C H3C

OH alcohol OH alcohol H3C R alkane coupling alkyne

H3C

M = Li or Mg IRCOONH3 NH2R NHR'R" H3C I alkyl iodide O ester H3C OR NH2 primary amine secondary amine tertiary amine

H3C

2. Dehydrohalogenation: Elimation
H H H

H H X

base

H2C

CH2

3. Preparation of Grignard Reagent

H3C X

Mg

ether

H3C

MgX

PREPARATION OF ALCOHOLS 1. Hydration

H H2C CH2 H H OH H

H 2O

Markovnikov addition

2. Grignard synthesis
O H3C

+
CH3

R-Mg-X

ether

H3C H3C R

OMgX

H 2O

H3C H3C

OH R

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SCH4U0 Ketones or aldehydes 3. Hydrolysis of alkyl halides

H3C X

CHEMISTRY Workbook

OH-

H3C

OH

X-

Usually requires a silver salt so can be very expensive 4. Reduction of ketones and aldehydes
O H3C O H3C CH3 H H2, Pt H2, Pt H H3C OH H3C H CH3 OH H

5. Hydrolysis of alkenes
KMnO4 H2C CH2 H H HO

H cis-addition

OH

6. Hydrolysis of Esters

O H3C OR

H or NaOH, H2O H3C

O OH

HO

REACTION OF ALCOHOLS 1. Reaction with hydrogen halides

H3C OH

+
H H

HX

H3C

2. Dehydration
H H H H

heat

H2C

CH2

OH

More substituted alkenes is favoured: 3>2>1 3. Ester Formation

O O H3C O R

+
OH

OH

H3C

4. Oxidation

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SCH4U0
PCC, CH2Cl2 OH O H3C H

CHEMISTRY Workbook
HO H3C H O KMnO4 CH3 H3C CH3

H3C

excess, KMnO4 O H3C OH

PREPARATION OF ETHERS 1. Condensation

H3C OH R

HO

H3C

PREPARATION OF ALKENES 1. Reduction of Alkynes

HC CH 1 H2 Pt H2C CH2

REACTION OF ALKENES 1. Addition of hydrogen. Catalytic hydrogenation

H2C CH2 H2, Pt

H3C

CH3

2. Addition of halogens
H2C CH2 X2 H H X X H H

3. addition of hydrogen halides

H3C CH2 HX X H3C CH3

Markovnikov addition 4. addition of water

H3C H2O H CH2 OH
+

H3C CH3

Markovnikovs addition 5. Hydroxylation

H2C CH2 KMnO4 H HO H

OH

PREPARATION OF ALKYNES Page 8 of 48

SCH4U0
H3C CH Na

CHEMISTRY Workbook
R C- Na
+

1. Reaction of metal acetylides with primary alkyl halides

H3C X H3C R R must be primary

REACTION OF ALKYNES 1. Addition of hydrogen

HC CH 1 H2, Pt 1 H 2, Pt

H2C

CH2

H3C

CH3

2. Addition of halogens
HC CH 2 X2 X H X X H X

3. Addition of hydrogen halides

H3C CH

2 HX H3C X

X H H

Markovnikov Addition

4. Formation of metal acetylides

H3C CH

Na H3C C- Na
+

PREPARATION OF ALDEHYDES 1. Oxidation of primary alcohols

OH H3C KMnO4 O H3C H

PREPARATION OF KETONES 1. Oxidation of secondary alcohols

OH H3C CH3 KMnO 4 H3C O CH3

REACTION OF ALDEHYDES and KETONES 1. Oxidation of aldehydes carboxylic acid

O O H3C H KMnO 4 H3C OH

2. Reduction of aldehydes 1 alcohols Page 9 of 48

SCH4U0
O H3C H

CHEMISTRY Workbook
H2, Pt H3C HO H H

10

3. Reduction of ketones 2 alcohol

O H2, Pt H3C CH3 HO H3C H CH3

PREPARATION OF CARBOXYLIC ACIDS 1. Oxidation of primary alcohols

OH H3C KMnO4, excess H3C O OH

2. Hydrolysis of Esters

O H3C OR

H or NaOH, H2O H3C

O OH

HO

REACTIONS OF CARBOXYLIC ACIDS 1. Acidity. Salt Formation

O H3C O

+
OH

NaOH

H3C

O- Na+

2. Conversion into Ester

O

+
OH

OH

O H3C O R

H3C

3. Conversion into Amide

O O H3C

+
OH

H2N

CH3

H3C

NH

CH3

REACTION OF BENZENE
H3C H3C Cl NO2 HNO3 H2SO 4

AlCl3

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SCH4U0
Intramolecular and Intermolecular Forces

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11

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 or hydrogen 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, as well 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 nuclei of 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 force Dipole - Dipole Interactions Occur between polar molecules having dipoles Molecules with dipoles are characterized by oppositely charged ends that are due to an unequal distribution of charge on the molecule The polarity of a molecule is determined by both the polarity of the Intramolecular bond and the shape of the molecule These forces are based on the simultaneous attraction of the electrons of one dipole by the dipoles of neighbouring molecules The strength of the force is related to the polarity of the given molecule Hydrogen 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
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12

attracted to the negative end of another molecule. Molecules have different degrees of polarity as determined 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 element 2. EN difference predict type bond (polar covalent vs. non-polar covalent) 3. SHOW presence of Dipole MOMENT (if any) Example:
H Cl Cl H O N H H H N H CH3 H H H H B H H H N H
+

3.44

F F

F
2.2

CH3

2.55

H
H

H3C

CH3

H Cl H

CH3

Cl

Be

Cl

Rank the following compounds in order of increasing boiling points. Explain the reason.

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SCH4U0
H3C H3C octane CH3 H3C OH butan-1-ol H3C CH3 2-methylbutan-2-ol OH CH3 CH3 CH3

CHEMISTRY Workbook ANSWER

13

2,3-dimethylbutane H3C

2-16 For each pair of compounds circle the compound you expect to have the higher boiling point. Explain your reasoning.
CH3 H3C H3C CH3 CH3 CH3

H3C

H H

CH3 H CH3

H H3C H3C H H OH H H H OH H H H H3C H3C N CH3 H N CH3 H3C CH3 CH3 OH

H3C H H

a)

b)

a) (CH3)3C-C(CH CH-CH2CH2-CH(CH3)2 3)3 and (CH3) 2 b) CH3(CH2)6CH3 and C H3(CH2)5CH2OH c) HOCH2-(CH2)4-CH2OH and (CH3)3CCH (OH)CH3 d) (CH3CH2C H2)2NH and (CH )3N 3CH2
CH3

HO

c)

d)

CH3

2-17 Circle the member of each pair that is more soluble in water. Show the molecular Page 13 of 48

SCH4U0 representation a) CH3CH2-O-CH2CH3 or CH3CH2CH2CH2CH3 b) CH3CH2NHCH3 or CH3CH2CH2CH3 c) CH3CH2OH or CH3CH2CH2CH2OH

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14

H3C H3C O

CH3
H3C N H

CH3

CH3

a)

H 3C

CH 3

b)

OH H3C H H

H3C

OH

c)

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ACTIVITY 1.2 THOUGHT LAB

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17

Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane

Number of C atoms Molecular Formula 1 2 3 4 5 6 7 8 9 10 CH4 C 2H 6 C 3H 8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22

Naming ORGANIC COMPOUNDS

Find the longest continuous carbon chain. Determine the root name for this parent chain. In cyclic compounds, the ring is usually considered the parent chain, unless it is attached to a longer chain of carbons; indicate a ring with the prefix cyclo before the root name. (When there are two longest chains of equal length, use the chain with the greater number of substituents.). Number the chain in the direction such that the position number of the first substituent is the smaller number. If the first substituents 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 on a nitrogen is designated with an N instead of 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. In alphabetizing, ignore prefixes like sec-, tert-, di, tri, etc., but include iso and cyclo. Always include a position number for each substituent, regardless of redundancies.

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Worksheet #2

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Worksheet #3 - QUESTIONS: naming alkanes and cycloalkanes

Practice Problems: name the following alkenes from their condensed structural formulas.

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STRUCTURE
CH3 H3C

NAME

STRUCTURE
H3C

NAME 20

SCH4U0 CH
3

CH3 CHEMISTRY Workbook H3C

CH3

H3C

CH3

H3C

CH3

3-ethyl-3,4dimethylhexane

Hexane

3-ethyl-2,5dimethylheptane

3-methyl-2isopropyloctane

4-tert-butyl-3,8dimethyldecane

2,7-dimethyl-4,5dipropyloctane

CH3

H3C

CH3

CH3

1-isopropyl-3methylcyclopentane
CH3
CH3

H3C CH3

1-ethyl-2,4dimethylcyclohexane

1-chloro-3ethylcyclooctane Page

cyclopropylcyclohexane

20 of 48
3,4-dichloro-2-

2,3,4-trimethylpentane

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21

Worksheet #4 - naming alkenes, cycloalkenes, alkynes Naming 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 either cis 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 molecule with both a double and a triple bond, whichever is closer to the end of the chain determines the direction of numbering. In the case where each would have the same position number, the double bond takes the lower number. In the name, ene comes before yne because of alphabetization.

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SCH4U0 STRUCTURE
H3C CH2

CHEMISTRY Workbook NAME STRUCTURE

CH3 H3C CH3 CH2

22

NAME

H3C CH H3C
CH3
H3C H3C CH3

CH3 CH3

CH3

CH3

CH3 H3C

H2C

CH3

H3C

CH3

Cl CH3

H3C

CH3
CH3

H3C

CH3

H3C

CH3

4-ethylcyclopentene

CH3

CH3

CH3 CH3 H3C

2-isopropyl-4methylpenta-1,3-diene

cis-2,4,6-octatriene

2,5-dimethylhex-3-yne

1,3-dimethylcyclopenta1,3-diene

2-methylpent-1-ene

3,4-dimethylpent-1-yne
H3C H3C

CH3

CH3

2,4-methylhex-2-ene

Page 22 of 48
4-methylhept-1-ene

4-chloro-1cyclopentyl-2methyl-1,3cycloheptadiene
2,4-methylhex-2-ene

SCH4U0

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24

Organic Chemistry Nomenclature Project

Hydrocarbons
H3C H3C H3C CH3 cyclopentane

1)____________________________
CH3 H3C H3C H3C CH3 CH3 CH3

2)__________________________________
H3C

H3C

CH3

3)____________________________

4)__________________________________

5-butyl-3,3,7,7-tetramethylnonane

2,3-dimethylbutane

5)____________________________

6)__________________________________

dimethylcyclopropyne

5-cyclopropyl-trans-3-heptene

7)____________________________

8)__________________________________
H3C CH3

4-butyl-2-ethyl-1-pentyl-1,4-cycloheptadiene

9)____________________________

10)__________________________________

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Name:
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Page 2

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Organic Chemistry Nomenclature Project

Aromatics

CH3

CH3

3-phenylpentane 1)____________________________

2)__________________________________

methyldiphenylmethane 3)____________________________
CH3

p cyclopropylethylbenzene

4)__________________________________

CH3

5)____________________________
CH3 O 2N NO2

5-butyl-3-ethyl-7-phenylnonane 6)__________________________________

CH3

7)____________________________
CH3 H3C

8)__________________________________

2,4-dimethyl-1-propylbenzene

9)____________________________

10)__________________________________

Name:
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Page 3

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27

Organic Chemistry Nomenclature Project

Halides
CH3 F Cl H3C Br o 1,3-dichlorobenzene

1)____________________________

2)__________________________________

3-bromo-2,4,4-trifluoro-6-iodoheptane

1,2,3,4,8-pentaiodo-1,3,5-cyclooctatriene

3)____________________________
Br H3C NO2 Br CH3

4)__________________________________
Cl

5)____________________________

6)__________________________________
Br F

F
6-chloro-1,1,1-trifluoro-2-phenyl-3-heptyne

Cl

7)____________________________

8)__________________________________
Br I H3C F Cl

4,7,9-tribromo-3-fluoro-6,8-dimethyl-cis-2-decene

9)____________________________

10)__________________________________

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Worksheet #8: REACTIONS OF HYDROCARBONS

1)

2) PREDICT PRODUCTS:

ADVANCED:

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29

ADVANCED

ADVANCED

3) For each of following reactions use structural diagram to show all reactants and products. Be sure to include all names, reaction conditions and catalysts. a. 3-ethyl-2-heptene reacts with water in the presence of acid b. 2-methyl-2-pentene reacts with hydrochloric acid c. tertiary-butane reacts with bromine gas in the presence of light d. halogenation of propane e. bromomethane is purged with NaI f. hydrogenation of 1,3-dimethylcyclopenta-1,3-diene g. Hydration of 2-isopropyl-4-methylpenta-1,3-diene h. Complete hydrohalogenation of 2,5-dimethylhex-3-yne i. Combustion (extreme oxidation) of cis-2,4,6-octatriene j. Complete halogenation of 3-methylhept-1-yne k. Octane burns in oxygen l. 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)Explain why it is that acid catalyzed addition of water to 1-

methylcyclobutene gives 1-methylcyclobutanol and not 2-methylcyclobutanol.

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Worksheet #9: Naming, Reactions, synthesis of Alcohols and Ethers

1. Indicate whether the following alcohols are primary, secondary, or tertiary.

H3C

a)

OH

CH3 H3C OH CH3

CH3

b)
OH

c)

OH

e)2-methyl-2-pentanol
OH

d) f)
CH3

2. Diethyl ether (commonly called ether) is a structural isomer of 1-butanol. Which compound 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 could use to distinguish between the two molecules. Give chemical reagents and the observation you would make. a)
H3C OH H3C O CH3
CH3

and

b)

H3C

H3C

OH CH3

OH and
OH

c)

and

OH

4) Give the products of the following reactions. Use N.R. if no reaction occurs
OH

a)

H3C
OH H3C

HCl

b)

CH3

+ K2Cr2O7

H+

c)

H3C

OH

+ conc.H2SO4

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SCH4U0 e) f)
CH3O-Na+ + H3C
Br

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31

H3C

OH + KMnO4 (excess)

OH

g)
H3C

+ PCC/CH2Cl2

H+

25C + dilute NaOH

CH3

h)

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.
CH3 CH3 OH

a)
O H3C

b) c)

H3C

CH3

CH3

2 steps

H3C

Br
OH

H3C

OH

d)
H3C OH

2 steps

O H3C OH

e)
Br O

f)

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:
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Page B4

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Organic Chemistry Nomenclature Project

Alcohols
H3C OH CH3

2-bromo-3,4-dihydroxypentane

1)____________________________

2)__________________________________
OH

2-hydroxy-1,3-cyclobutadiene

3)____________________________

4)__________________________________

H3C

Cl Cl

Cl OH

I CH3

OH

4-hydroxy-trans-2-hexane

5)____________________________
OH

6)__________________________________

OH
p 1,2-dihydroxybenzene

7)____________________________
CH3 CH3 HO CH3 CH3 CH3

8)__________________________________

3,4,4-triphenyl-2-butanol

9)____________________________

10)__________________________________

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Name:

Page B5 Organic Chemistry Nomenclature Project

Ethers
H3C O CH3

4-methoxy-2-pentyne

1)____________________________

2)__________________________________
HO

H3C
2-chloroxypropane

3)____________________________

4)__________________________________
H3C O O

H3C
dipropylether

5)____________________________
H3C H3C O

6)__________________________________

2,6-dibromo-5-fluoroxy-4-methyl-cis-2-heptene

7)____________________________

8)__________________________________

3-iodo-3-methoxy-2-phenyl-1-propanol

9)____________________________

10)__________________________________

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Worksheet #10 Naming, Synthesis, Reactions of Aldehydes, Ketones, Carboxylic Acids

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35

PRACTICE: Name the following compounds

1.

2.

3 4

5 6

8 9 10
Give the products of the following reactions. Use N.R. if no reaction occurs.
H3C O H H2

a)

Pt

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SCH4U0
H3C O H

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36

KMnO4, H+

b)

O H3C CH3 O CH3 O H3C O H3C O H3C H CH Na

+

HCl

c)

K2Cr2O7, H+

d) H3C

+
OH

H2O

e)

+
OH

Na OH

f)

K2Cr2O7, H+

g)

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Name:

Page B6 Organic Chemistry Nomenclature Project

Aldehydes and Ketones

O H3C
propanal

CH3

1)____________________________

2)__________________________________
H3C H3C O CH3

2,4-dichlorobenzaldehyde

3)____________________________

4)__________________________________
O H3C CH3 O CH3

4-cyclobutyl-trans-2-pentenal

5)_____________________________
O CH2

6)__________________________________

2,6-difluoro-3,3,5-trihydroxycyclooctanone

7)___________________________

8)__________________________________

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SCH4U0
pent-4-yn-2-one

CHEMISTRY Workbook
4-chloroxy-1,2-dibromo-2-methyl-4-nitro-butanal

38

9)____________________________

10)__________________________________

Name:

Page B7 Organic Chemistry Nomenclature Project

Carboxylic Acids
HO O OH OH CH3

pentanoic acid

1)____________________________

2)__________________________________
H3C H3C H3C H3C O OH CH3 CH3

2,5-dimethyl-cis-3-heptenoic acid

3)____________________________

4)__________________________________

HO CH3 O

4-cyclopropyl-2-nitro-3-butynoic acid

5)____________________________

6)__________________________________
OH O H3C CH

3-methoxybenzoic acid

7)____________________________

8)__________________________________
H3C I OH I CH3 O O

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SCH4U0
butanedioic acid

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39

9)____________________________

10)__________________________________

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Name:

Page B8 Organic Chemistry Nomenclature Project

Esters

O CH3 H3C propyl butanoate O

1)____________________________

2)__________________________________

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42

phenyl hexanoate

dichloromethyl 2-ethoxypropanoate

3)____________________________

4)__________________________________
Br H3C O O CH3 CH3

methyl acetate

5)____________________________

6)__________________________________

2-phenyl-trans-3-pentenyl 2-hydroxybenzoate

2-nitrocyclohexyl ethanoate

7)____________________________
O H3C O

8)__________________________________
O

CH3 CH3

H3C O

CH3 O

9)____________________________

10)__________________________________

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Name:

Page B9 Organic Chemistry Nomenclature Project

Amines
CH3 N H3C CH3

ethylmethylamine 1)____________________________

2)__________________________________
H3C HO NH CH3

3-amino-4,5,6,7-tetramethylnonane

3)____________________________

4)__________________________________

2,3-diamino-N3-chloro-N2-methylpentane

cyclopentyl 2-amino-N-methylbutanoate

5)____________________________
N

6)__________________________________

5-aminohex-1-yn-3-one

7)____________________________

8)__________________________________
OH HN CH3

H2N

CH3

N,N-dimethylaniline

9)____________________________

10)_________________________________ Page 43 of 48

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Name:

Page B10 Organic Chemistry Nomenclature Project

Amides

H2N O CH3
2-bromo-N-ethylpropanamide

1)____________________________

2)__________________________________
NH2 H3C N F O CH3

3-cyclopropyloxy-N-ethyl-N,6-dimethylheptanamide

3)____________________________

4)__________________________________
NO2 H3C NH O

N-iodo-N-methyl-3-pentynamide

5)____________________________
O NH2 Br Br CH3 O CH3

6)__________________________________

N-cycloheptyl-N-phenylacetamide

7)____________________________
H3C CH3 O H3C H3C O OH O NH2

8)__________________________________

N,N-dihydroxybenzamide

9)____________________________

10)__________________________________

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Worksheet #11
SCH4U0 CHEMISTRY Workbook 45

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SCH4U0

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SCH4U0

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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. 2. 3. 4. 5. 6. 7. 8. fluoroethane from ethanol 3-methylpentane from 3-methyl-3-pentanol acetone from propene acetic acid from chloroethane 2-iodopropane from acetone 1-butanol reacts in the presence of concentrated sulfuric acid ethyl ethanoate from ethane isopropylbenzene from benzene

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SCH4U0 condensed formulas and structural formulas.

1. 3. 5. dichloromethane cis-2,4,6-octatriene cyclohexylcyclohexane 6. 2.

CHEMISTRY Workbook

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5. Draw the following hydrocarbons. Make sure you know how to do line diagrams,

3,5-dichloro-4-cyclobutylheptane 4.

4-chloro-1-cyclopentyl-2-methyl-1,3cycloheptadiene

3-ethyl-5,5-diisopropyl-2-methyloctane

7. 9. 10.

2-methyl-4nitroocta-2-ene-5-yne

8.

5-chloro-3-ethyl-1-nitro-1,4-cyclooctadiene

trans-2,3-dichloro-6-isopropyl-4,5,7-trimethyl-2,4,6-decatriene 1,2-dibromo-3,8-dichloro-5-ethyl-4-nitrooctacis-1-trans-3,7-triene-5-yne

Name the following hydrocarbons.

Cl

Cl

3.
H3C

H C C H

H C C H

CH3

4.

5.

Br H HC Cl C C C Cl

6.
H C H H C H H

C Cl

7.

Cl

NH2

8.

CH3(CH2)6CHCH2

CH3CH2C(CH3)2CH2CH3

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