Organic Chemistry For Health Science

Learning Commons

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3
Alkynes
A m i d es
s
at ic
m
Ar o
Hydration of Alkenes
T hio
ls s
Salt
Acetal Formation

5
USER GUIDE 7
UNIT I 9
ACIDS & BASES 11
1.1 – ACIDS & BASE CHEMISTRY 13
1.2 – GRAM EQUIVALENTS-‐NORMALITY-‐TITRATION 15
1.3 – PH -‐ POH – [H+] – [-‐OH] 17
1.4 – BUFFERS 19

ALKANES 21
1.5 – NAMING ALKANES 23
1.6 – FUNCTIONAL GROUPS 25
1.7 – DRAWING STRUCTURES 27
1.8 – CONFORMERS & ISOMERS 29

PRACTICE TESTS
1A 31
1B 39

UNIT II 47
ALKENES, ALKYNES & AROMATICS 49
2.1 – NAMING ALKENES, ALKYNES, & AROMATICS 51
2.2 – CIS/TRANS 53
2.3 – POLYMERS 55
2.4 – REACTIONS OF ALKENES, ALKYNES, & AROMATICS 57

ALCOHOLS, PHENOLS, ETHERS, THIOLS, & HALOGENS 59
2.5 – NAMING ALCOHOLS, PHENOLS, ETHERS, THIOLS, & HALOGENS 61
2.6 – REACTIONS OF ALCOHOLS, PHENOLS, ETHERS, THIOLS, & HALOGENS 63

PRACTICE TESTS
2A 65
2B 73

UNIT III 81
AMINES, ALDEHYDES, KETONES, CARBOXYLIC ACIDS, ESTERS, & AMIDES 83
3.1 – NAMING AMINES, ALDEHYDES, & KETONES 85
3.2 – NAMING CARBOXYLIC ACIDS, ESTERS, & AMIDES 87
3.3 – REACTIONS – TESTS (LUCAS, BENEDICTS, & TOLLENS) 89
3.4 – REACTIONS OF CARBONYLS 91

CARBOHYDRATES 93
3.5 – CARBOHYDRATE NOMENCLATURE 95
3.6 – REACTIONS OF CARBOHYDRATES 97
3.7 – CONVERTING FISCHER TO CYCLIC 99

PRACTICE TESTS
3A 101
3B 109

TOOLS 117
NOMENCLATURE 119
COMMON FUNCTIONAL GROUPS 120
SIGNIFICANT FIGURES 121
PERIODIC TABLE OF THE ELEMENTS 123

7

Thank you for choosing to use this workbook provided by the PLUS program at Eastern
Washington University! The purpose of this book is to provide a medium to which students
and tutors can enhance their subject knowledge by focusing on fluency and speed, which are
fundamental to success on exams. This workbook is intended for use by a tutor who has
successfully completed the course in question, in a 1-‐on-‐1 or small group format. In addition,
this workbook assumes that the reader has access to a textbook for explanations not
provided in this material. This book is intended to be supplemental to a textbook for use by a
tutor and a student.
NO TE:

These worksheets and
Worksheets: practice exams are
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Ø BACK = ANSWER KEY and therefore, the most
Ø Print off/copy for student problems encountered
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Practice Exams: The theory: if a student
Ø 3-‐4 pages of simulated exam type questions can complete difficult
o There are two types of exams: practice problems with a
§ A – very similar to worksheets tutor, they can excel
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Ø TREAT IT LIKE A REAL EXAM standard exam level.
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Ø Allow no more than 50-‐55 minutes to complete.
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Ø Grade exam for students just like a professor would
Ø Or grade exam with student – learn from mistakes!

In order to get the most out of the practice exams, it is imperative to simulate a test-‐like
environment when taking these exams. Many students unfortunately suffer from test anxiety
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provide a means to address and remedy them.
Happy tutoring!

47

49
# of Bonds Type of Compound Compounds

to
Alphabetical
1 Alkane
2 Alkene MEMORIZE
3 Alkyne
Naming is the same as alkanes,

but you change the suffix –ane,
to –ene or –yne.
Cis – on the same side

Trans – across from each other
[remember the ‘A’ in trans
for ‘A’cross from each other]
Types of Rxns

Addition à
Substance adds to the multiple bond (like
double of triple bond) to yield a product with only Markovnikov’s
a single bond and the new substance attached. Rule

Hydrogens
always attach to
the carbon with
Elimination à the most
A saturated compound yields an hydrogens!
unsaturated product by loss of groups from
adjacent carbons.
Aromatic position
naming à only for
benzenes with 2
groups
Substitution à
When an atom or group of atoms is replaced
by another atom or group of atoms.

51
2.1 – Worksheet
Namin g Alkenes, A lkynes, & Aromatics
Please complete the following table either by providing the name or the structure of the
compound. Don’t worry about cis and trans nomenclature but please use ortho, meta & para.

6-‐isopropyl-‐5-‐propyl-‐9-‐

methyldeca-‐3.6-‐diene

5-‐ethyl-‐2-‐methylnon-‐3-‐yne p-‐Iodonitrobenzene

4-‐chloro-‐3-‐

methylnitrobenzene

2.1 – Worksheet – Key

Namin g Alkenes, A lkynes, & Aromatics
Please complete the following table either by providing the name or the structure of the
compound. Don’t worry about cis and trans nomenclature but please use ortho, meta & para.

4-‐ethyl-‐3-‐methylhepta-‐2,4-‐
4-‐methylpent-‐2-‐ene 5,6-‐dimethylhept-‐2-‐yne
diene

6-‐isopropyl-‐5-‐propyl-‐9-‐
Toluene or Methylbenzene m-‐bromochlorobenzene
methyldeca-‐3.6-‐diene

5-‐ethyl-‐2-‐methylnon-‐3-‐yne p-‐Iodonitrobenzene Benzoic Acid

5-‐sec-‐butyl-‐3-‐isobutyl-‐1-‐
o-‐pentylaniline m-‐Xylene
cyclohexene

4-‐chloro-‐3-‐ 3-‐bromo-‐5-‐
6-‐methyl-‐5-‐phenyloct-‐2-‐yne
methylnitrobenzene ethylbenzaldehyde

53
2.2 – Worksheet
Cis/ Trans
Please identify if the following are cis (with a circle) or trans (with a square) compounds. If
the compound is neither cis or trans, leave it blank.
Please provide the cis and trans isomers of 3-‐pentene
Please provide the cis and trans isomers of 3,4,6,7-‐tetramethyloct-‐3-‐ene
Please name the following with the appropriate cis and trans prefix.


Cis/ Trans
Please identify if the following are cis (with a circle) or trans (with a square) compounds. If
the compound is neither cis or trans, leave it blank.
Please provide the cis and trans isomers of 3-‐pentene
Please provide the cis and trans isomers of 3,4,6,7-‐tetramethyloct-‐3-‐ene
Please name the following with the appropriate cis and trans prefix.
Cis-‐2-‐methyloct-‐3-‐ene Trans-‐5-‐ethyl-‐2-‐ Cis-‐4,5-‐diethyloct-‐4-‐ene

methylhept-‐3-‐ene
55
2.3 – Worksheet
Polymers
Below is the structure of the monomer ethylene. Please write the structure of a segment of
polyethylene with brackets around one segment of the polymer.
Below is the structure of the monomer propylene. Please write the structure of a segment of
polypropylene with brackets around two segments of the polymer.
Below is the structure of the monomer acrylonitrile. Please write the structure of a segment of
Acrilan (polyacrylonitrile) with brackets around three segments of the polymer.
Below is two segments of the structure of the polymer PVC or poly(vinyl chloride). Please
provide the structure of its monomer vinyl chloride.
Three segments of the polymer poly(vinyl acetate) is shown below. Please provide the
structure of its monomer vinyl acetate.


Polymers
Below is the structure of the monomer ethylene. Please write the structure of a segment of
polyethylene with brackets around one segment of the polymer.
Below is the structure of the monomer propylene. Please write the structure of a segment of
polypropylene with brackets around two segments of the polymer.
Below is the structure of the monomer acrylonitrile. Please write the structure of a segment of
Acrilan (polyacrylonitrile) with brackets around three segments of the polymer.
Below is two segments of the structure of the polymer PVC or poly(vinyl chloride). Please
provide the structure of its monomer vinyl chloride.
Three segments of the polymer poly(vinyl acetate) is shown below. Please provide the
structure of its monomer vinyl acetate.
57
2.4 – Worksheet
Reaction s
Please identify if the following reactions as addition, subtraction, or elimination reactions.

Please provide the products, reactants or the starting material to the following reactions, if
there is more than one product, circle the major.


Reaction s
Please identify if the following reactions as addition, subtraction, or elimination reactions.

Substitution Elimination

Addition Substitution

Please provide the products, reactants or the starting material to the following reactions, if
there is more than one product, circle the major.
59
Compounds to MEMORIZE
Types of Compounds Naming

Alcohols
1. Name Parent
2. Number with priority
to hydroxyl group
3. Add suffix –ol

Phenols
1. Identify substituents
2. Number from hydroxyl
group
3. Add suffix phenol

Ethers
1. Identify two o rganic
groups
2. Add suffix ether
OR
1. If the ether is a
functional group, add
oxy instead of -‐yl to
the functional group
name.

Thiols
Similar to alcohols
1. Add thiol to the end of
the parent chain
2. Add the number of
location of the sulfur.

Halogens
1. Number location of
halide and use terms
Fluoro, Chloro, Bromo,
& Iodo.
2. No suffix change.

61
2.5 – Worksheet
Naming Alcohols, Phenols, Ethers, Thiols & Halogens
Please provide the name or structure of the following compounds

1,4-‐dioxane

2-‐sec-‐butyl-‐5-‐tert-‐

butylphenol

4-‐chloro-‐3-‐ethoxyheptane

6-‐ethyl-‐2-‐fluoro-‐3-‐

propoxyoctanethiol


Naming Alcohols, Phenols, Ethers, Thiols & Halogens
Please provide the name or structure of the following compounds

3-‐methylpentan-‐2-‐ol m-‐chlorophenol 1,4-‐dioxane

2-‐isopropyl-‐3-‐ Methyl propyl ether OR

3-‐propylhexane-‐2,4-‐diol
methylbutanethiol 1-‐methoxypropane

2-‐sec-‐butyl-‐5-‐tert-‐
1-‐Bromo-‐3-‐Iodocyclohexane Glycerol
butylphenol

o-‐butoxyphenol 4-‐chloro-‐3-‐ethoxyheptane 6-‐ethyl-‐3,3-‐dimethyloct-‐5-‐en-‐2-‐ol

6-‐ethyl-‐2-‐fluoro-‐3-‐ 4-‐chloro-‐2-‐ 2-‐bromo-‐4-‐isopropyl-‐3-‐

propoxyoctanethiol methoxycyclopentanol pentoxyphenol

63
2.6 – Worksheet
Reaction s of A lcohols
Please predict the products or reactants in the following reactions. If there is more than one
product, please circle the major. If there is no reaction, simply write ‘No Rxn’.


Reaction s
Please predict the products or reactants in the following reactions. If there is more than one
product, please circle the major. If there is no reaction, simply write ‘No Rxn’.
No
Rxn
65
Practice T est – 2A
1. Please complete the following table by providing either the name or the structure of the
following compounds. (30)

p-‐nitroaniline

THF

2-‐tert-‐butyl-‐5-‐chlorophenol

1-‐bromo-‐2-‐methyl-‐3-‐
Ethylene oxide
propoxybutanethiol

2. Please identify the following as either cis (circle), trans (square) or neither (blank). (6)
3. Please provide the cis and trans isomers for 4,5-‐dimethyloct-‐4-‐ene. (4)
4. Please provide the names of the following compounds including the appropriate cis and
trans prefixes when applicable. (6)
5. Below is the polymer polystyrene used in many foams and plastics. Please provide the
structure of its monomer styrene. (3)
6. Below is the monomer propylene. Please provide the structure of two segments of its
polymer named polypropylene. (3)
67
7. Please identify whether the following reactions are addition, substitution, elimination or
rearrangement. (3)
8. Please provide all of the products, reactants, or starting material for the following
reactions. If there is major product, please specify with a circle. (21)
(5)
(4)
(2) (6)
m-Xylene
(4)

(4)
(5)
(3)
(4)
(4)
(2) (2)
100
69
Practice T est – 2A – KEY

1. Please complete the following table by providing either the name or the structure of the

2-‐cyclopropyl-‐3-‐ 6-‐bromo-‐2,5-‐dimethylhept-‐3-‐
m-‐methyoxybenzaldehyde
isopropylhex-‐3-‐ene yne

p-‐nitroaniline Dipropyl ether 3-‐Iodo-‐2methyl-‐pentanethiol

5-‐ethyl-‐3,4-‐dimethylhepta-‐
THF Ethylene Glycol
1,4-‐diene

3-‐sec-‐butyl-‐2-‐fluorobenzoic
o-‐Xylene 2-‐tert-‐butyl-‐5-‐chlorophenol
acid

4-‐ethyl-‐4,5-‐dimethyl-‐3-‐ 1-‐bromo-‐2-‐methyl-‐3-‐
Ethylene oxide
octanol propoxybutanethiol

2. Please identify the following as either cis (circle), trans (square) or neither (blank). (6)
3. Please provide the cis and trans isomers for 4,5-‐dimethyloct-‐4-‐ene. (4)
4. Please provide the names of the following compounds including the appropriate cis and
trans prefixes when applicable. (6)
Trans-‐4,5-‐diethyl-‐2-‐ Cis-‐2,3,4,5-‐ 3-‐ethyl-‐2-‐

methyloct-‐4-‐ene tetramethylhept-‐3-‐ene methylpent-‐2-‐ene
5. Below is the polymer polystyrene used in many foams and plastics. Please provide the
structure of its monomer styrene. (3)
6. Below is the monomer propylene. Please provide the structure of two segments of its
polymer named polypropylene. (3)
71

7. Please identify whether the following reactions are addition, substitution, elimination or
rearrangement. (3)
Substitution
Addition
Rearrangement
(5)
(4)
(2) (6)
m-Xylene
(4)
Na2Cr2O7 H2
Pd Catalyst


(4)
(5)
(3)
(4)
(4)
(2) (2)
73
Practice T est – 2B
1. Please provide all of the products or reactants of the following reactions as well as the names
of the compounds when prompted. If there is a major product please specify with a circle and
only provide the name of the major. (27)
(9)
HCl
Name: Name:
(8)
HNO3
H2SO4 Catalyst
Name: (Only name one Name:

of the products)
(10)
Br2
FeBr3
Name: Name: Name:
2. The reaction below results in two isomeric products. Please provide the structure and names of
both isomeric products using appropriate cis and trans knowledge and nomenclature. (10)
Name:
Name: Name:

3. Plastics are made through polymerization of an alkene monomer. Below is three segments of
the polymer Acrilian. Please provide the structure of its monomer Acrylonitrile. (3)
4. Below is the monomer vinyl chloride. Please provide the structure of two segments of its
polymer poly(vinyl chloride) – PVC. (3)
5. Please provide the structure of the following reactants and provide the structure of the
product. (6)
Name: Name:
6. How could you prepare 3,4-‐dichloro-‐2,5-‐dimethylhexane from an alkene? Please indicate
any inorganic reagents needed in the process in addition to the structure of the starting
material and products. (6)
Name:
75
7. Please complete the following table by providing the appropriate structure or name of the

4-‐isopropylhepta-‐2,4-‐diene

Glycerol

8. Please identify the following as cis (circle), trans (square) or neither (blank). (6)
9. Please provide the products or reactants and classify the following reactions as addition,
elimination, substitution, or rearrangement. Also, please provide the names of the compounds
when prompted. (8)
(5)
Type:
Name:
(3)
Type:

when prompted. (5)
(5)
Type:
Name:
11. Please provide the products, reactants or starting materials for the following reactions. If
there is a major product, please circle it. If there is no reaction write ‘no rxn’. (14)
(4)
(1)
(7)
(2)
100
77
Practice T est – 2B – KEY

1. Please provide all of the products or reactants of the following reactions as well as the names
of the compounds when prompted. If there is a major product please specify with a circle and
only provide the name of the major. (27)
(9)
HCl
Name: 4-‐ethyl-‐3-‐ Name: 3-‐chloro-‐2-‐

methyl-‐2-‐petnene ethyl-‐3-‐methylpentane
(8)
HNO3
H2SO4 Catalyst
Name: o-‐Xylene Name: 1,2-‐dimethyl-‐

3-‐nitrobenzene
(10)
Br2
FeBr3
Name: 2,6-‐dimethylbenzoic Name: 3-‐bromo-‐2,6-‐ Name: 4-‐bromo-‐2,6-‐

acid dimethylbenzoic acid dimethylbenzoic acid
2. The reaction below results in two isomeric products. Please provide the structure and names of
both isomeric products using appropriate cis and trans knowledge and nomenclature. (10)
Name: 3,4,5-‐
trimethyl-‐4-‐heptene
Name: Trans 3,4,5-‐ Name: Cis 3,4,5-‐

trimethylhept-‐3-‐ene trimethylhept-‐3-‐ene


3. Plastics are made through polymerization of an alkene monomer. Below is three segments of
the polymer Acrilian. Please provide the structure of its monomer Acrylonitrile. (3)
4. Below is the monomer vinyl chloride. Please provide the structure of two segments of its
polymer poly(vinyl chloride) – PVC. (3)
5. Please provide the structure of the following reactants and provide the structure of the
product. (6)
Name: 3-‐ethyl-‐4-‐ Name: 3-‐methylpentane

methylpentanethiol thiol
6. How could you prepare 3,4-‐dichloro-‐2,5-‐dimethylhexane from an alkene? Please indicate
any inorganic reagents needed in the process in addition to the structure of the starting
material and products. (6)
Name: 2,5-‐dimethyl-‐
3-‐hexene
79

7. Please complete the following table by providing the appropriate structure or name of the

4-‐isopropylhepta-‐2,4-‐diene THF o-‐propoxyphenol

Isopropyl alcohol m-‐fluorobenzaldehyde Glycerol

8. Please identify the following as cis (circle), trans (square) or neither (blank). (6)
when prompted. (8)
(5)
H2
Pd Catalyst Type: Addition
Name: 3-‐ethyl-‐7-‐
methyl-‐4-‐nonyne
(3)
Type: Substitution

when prompted. (5)
(5)
H2SO4 Type: Elimination
Catalyst
Name: 5-‐Iodo-‐4-‐methyl-‐
3-‐hexanol
10. Please provide the products, reactants or starting materials for the following reactions. If
there is a major product, please circle it. If there is no reaction write ‘no rxn’.
(4)
(1)
No Rxn
(7)
(2)
100
117

119

121

123

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Learning Commons

# of Bonds Type of Compound Compounds

Naming is the same as alkanes,

Cis – on the same side

Types of Rxns

2.1 – Worksheet – Key

5-­‐ethyl-­‐2-­‐methylnon-­‐3-­‐yne p-­‐Iodonitrobenzene Benzoic Acid

Please provide the cis and trans isomers of 3-­‐pentene

Please provide the cis and trans isomers of 3,4,6,7-­‐tetramethyloct-­‐3-­‐ene

2.2 – Worksheet – Key

Please provide the cis and trans isomers of 3-­‐pentene

Please provide the cis and trans isomers of 3,4,6,7-­‐tetramethyloct-­‐3-­‐ene

Cis-­‐2-­‐methyloct-­‐3-­‐ene Trans-­‐5-­‐ethyl-­‐2-­‐ Cis-­‐4,5-­‐diethyloct-­‐4-­‐ene

2.3 – Worksheet – Key

2.4 – Worksheet – Key

Compounds to MEMORIZE

Types of Compounds Naming

2.5 – Worksheet – Key

3-­‐methylpentan-­‐2-­‐ol m-­‐chlorophenol 1,4-­‐dioxane

2-­‐isopropyl-­‐3-­‐ Methyl propyl ether OR

o-­‐butoxyphenol 4-­‐chloro-­‐3-­‐ethoxyheptane 6-­‐ethyl-­‐3,3-­‐dimethyloct-­‐5-­‐en-­‐2-­‐ol

6-­‐ethyl-­‐2-­‐fluoro-­‐3-­‐ 4-­‐chloro-­‐2-­‐ 2-­‐bromo-­‐4-­‐isopropyl-­‐3-­‐

2.6 – Worksheet – Key

Practice T est – 2A – KEY

p-­‐nitroaniline Dipropyl ether 3-­‐Iodo-­‐2methyl-­‐pentanethiol

Practice T est – 2A – KEY

Trans-­‐4,5-­‐diethyl-­‐2-­‐ Cis-­‐2,3,4,5-­‐ 3-­‐ethyl-­‐2-­‐

Practice T est – 2A – KEY

Practice T est – 2A – KEY

Name: (Only name one Name:

Name: Name: Name:

Practice T est – 2B – KEY

Name: 4-­‐ethyl-­‐3-­‐ Name: 3-­‐chloro-­‐2-­‐

Name: o-­‐Xylene Name: 1,2-­‐dimethyl-­‐

Name: 2,6-­‐dimethylbenzoic Name: 3-­‐bromo-­‐2,6-­‐ Name: 4-­‐bromo-­‐2,6-­‐

Name: Trans 3,4,5-­‐ Name: Cis 3,4,5-­‐

Practice T est – 2B – KEY

Name: 3-­‐ethyl-­‐4-­‐ Name: 3-­‐methylpentane

Practice T est – 2B – KEY

4-­‐isopropylhepta-­‐2,4-­‐diene THF o-­‐propoxyphenol

Isopropyl alcohol m-­‐fluorobenzaldehyde Glycerol

Вам также может понравиться

5-‐ethyl-‐2-‐methylnon-‐3-‐yne p-‐Iodonitrobenzene Benzoic Acid

Please provide the cis and trans isomers of 3-‐pentene

Please provide the cis and trans isomers of 3,4,6,7-‐tetramethyloct-‐3-‐ene

Please provide the cis and trans isomers of 3-‐pentene

Please provide the cis and trans isomers of 3,4,6,7-‐tetramethyloct-‐3-‐ene

Cis-‐2-‐methyloct-‐3-‐ene Trans-‐5-‐ethyl-‐2-‐ Cis-‐4,5-‐diethyloct-‐4-‐ene

3-‐methylpentan-‐2-‐ol m-‐chlorophenol 1,4-‐dioxane

2-‐isopropyl-‐3-‐ Methyl propyl ether OR

o-‐butoxyphenol 4-‐chloro-‐3-‐ethoxyheptane 6-‐ethyl-‐3,3-‐dimethyloct-‐5-‐en-‐2-‐ol

6-‐ethyl-‐2-‐fluoro-‐3-‐ 4-‐chloro-‐2-‐ 2-‐bromo-‐4-‐isopropyl-‐3-‐

p-‐nitroaniline Dipropyl ether 3-‐Iodo-‐2methyl-‐pentanethiol

Trans-‐4,5-‐diethyl-‐2-‐ Cis-‐2,3,4,5-‐ 3-‐ethyl-‐2-‐

Name: 4-‐ethyl-‐3-‐ Name: 3-‐chloro-‐2-‐

Name: o-‐Xylene Name: 1,2-‐dimethyl-‐

Name: 2,6-‐dimethylbenzoic Name: 3-‐bromo-‐2,6-‐ Name: 4-‐bromo-‐2,6-‐

Name: Trans 3,4,5-‐ Name: Cis 3,4,5-‐

Name: 3-‐ethyl-‐4-‐ Name: 3-‐methylpentane

4-‐isopropylhepta-‐2,4-‐diene THF o-‐propoxyphenol

Isopropyl alcohol m-‐fluorobenzaldehyde Glycerol