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5 USER GUIDE 7 UNIT I ACIDS & BASES 1.1 – ACIDS & BASE CHEMISTRY 1.2 – GRAM EQUIVALENTS-­‐NORMALITY-­‐TITRATION 1.3 – PH -­‐ POH – [H+] – [-­‐OH] 1.4 – BUFFERS ALKANES 1.5 – NAMING ALKANES 1.6 – FUNCTIONAL GROUPS 1.7 – DRAWING STRUCTURES 1.8 – CONFORMERS & ISOMERS PRACTICE TESTS 1A 1B 9 11 13 15 17 19 21 23 25 27 29 31 39 UNIT II 47 ALKENES, ALKYNES & AROMATICS 2.1 – NAMING ALKENES, ALKYNES, & AROMATICS 2.2 – CIS/TRANS 2.3 – POLYMERS 2.4 – REACTIONS OF ALKENES, ALKYNES, & AROMATICS 49 51 53 55 57 ALCOHOLS, PHENOLS, ETHERS, THIOLS, & HALOGENS 2.5 – NAMING ALCOHOLS, PHENOLS, ETHERS, THIOLS, & HALOGENS 2.6 – REACTIONS OF ALCOHOLS, PHENOLS, ETHERS, THIOLS, & HALOGENS 59 61 63 PRACTICE TESTS 2A 2B 65 73 UNIT III 81 AMINES, ALDEHYDES, KETONES, CARBOXYLIC ACIDS, ESTERS, & AMIDES 3.1 – NAMING AMINES, ALDEHYDES, & KETONES 3.2 – NAMING CARBOXYLIC ACIDS, ESTERS, & AMIDES 3.3 – REACTIONS – TESTS (LUCAS, BENEDICTS, & TOLLENS) 3.4 – REACTIONS OF CARBONYLS 83 85 87 89 91 CARBOHYDRATES 3.5 – CARBOHYDRATE NOMENCLATURE 3.6 – REACTIONS OF CARBOHYDRATES 3.7 – CONVERTING FISCHER TO CYCLIC PRACTICE TESTS 3A 3B 93 95 97 99 TOOLS NOMENCLATURE COMMON FUNCTIONAL GROUPS SIGNIFICANT FIGURES PERIODIC TABLE OF THE ELEMENTS 101 109 117 119 120 121 123 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:
Worksheets: Ø
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1 page of problems on a focused topic FRONT = BLANK BACK = ANSWER KEY Print off/copy for student Or work on with student Consult textbook for detailed explanation of topic Practice Exams: These worksheets and
practice exams are
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§ A – very similar to worksheets tutor, they can excel
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47 49 1
2
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Alphabetical # of Bonds Type of Compound Alkane Alkene Alkyne Compounds to MEMORIZE 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 a single bond and the new substance attached. Elimination à A saturated compound yields an unsaturated product by loss of groups from adjacent carbons. Markovnikov’s Rule Hydrogens always attach to the carbon with the most hydrogens! 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-­‐methylpent-­‐2-­‐ene 4-­‐ethyl-­‐3-­‐methylhepta-­‐2,4-­‐
diene 5,6-­‐dimethylhept-­‐2-­‐yne Toluene or Methylbenzene m-­‐bromochlorobenzene 6-­‐isopropyl-­‐5-­‐propyl-­‐9-­‐
methyldeca-­‐3.6-­‐diene 5-­‐ethyl-­‐2-­‐methylnon-­‐3-­‐yne p-­‐Iodonitrobenzene Benzoic Acid 5-­‐sec-­‐butyl-­‐3-­‐isobutyl-­‐1-­‐
cyclohexene o-­‐pentylaniline m-­‐Xylene 4-­‐chloro-­‐3-­‐
methylnitrobenzene 3-­‐bromo-­‐5-­‐
ethylbenzaldehyde 6-­‐methyl-­‐5-­‐phenyloct-­‐2-­‐yne 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. 2.2 – Worksheet – Key
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-­‐
methylhept-­‐3-­‐ene Cis-­‐4,5-­‐diethyloct-­‐4-­‐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. 2.3 – Worksheet – Key
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. 2.4 – Worksheet – Key
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 2.5 – Worksheet – Key
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-­‐
methylbutanethiol Methyl propyl ether OR 1-­‐methoxypropane 3-­‐propylhexane-­‐2,4-­‐diol 1-­‐Bromo-­‐3-­‐Iodocyclohexane 2-­‐sec-­‐butyl-­‐5-­‐tert-­‐
butylphenol Glycerol o-­‐butoxyphenol 4-­‐chloro-­‐3-­‐ethoxyheptane 6-­‐ethyl-­‐3,3-­‐dimethyloct-­‐5-­‐en-­‐2-­‐ol 6-­‐ethyl-­‐2-­‐fluoro-­‐3-­‐
propoxyoctanethiol 4-­‐chloro-­‐2-­‐
methoxycyclopentanol 2-­‐bromo-­‐4-­‐isopropyl-­‐3-­‐
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’. 2.6 – Worksheet – Key
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 Ethylene oxide 1-­‐bromo-­‐2-­‐methyl-­‐3-­‐
propoxybutanethiol Practice T est – 2A
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 Practice T est – 2A
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) Practice T est – 2A
9. Please provide all of the products, reactants, or starting material for the following reactions. If there is major product, please specify with a circle. (24) (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 following compounds. (30) 2-­‐cyclopropyl-­‐3-­‐
isopropylhex-­‐3-­‐ene m-­‐methyoxybenzaldehyde 6-­‐bromo-­‐2,5-­‐dimethylhept-­‐3-­‐
yne p-­‐nitroaniline Dipropyl ether 3-­‐Iodo-­‐2methyl-­‐pentanethiol THF 5-­‐ethyl-­‐3,4-­‐dimethylhepta-­‐
1,4-­‐diene Ethylene Glycol o-­‐Xylene 2-­‐tert-­‐butyl-­‐5-­‐chlorophenol 3-­‐sec-­‐butyl-­‐2-­‐fluorobenzoic acid Ethylene oxide 4-­‐ethyl-­‐4,5-­‐dimethyl-­‐3-­‐
octanol 1-­‐bromo-­‐2-­‐methyl-­‐3-­‐
propoxybutanethiol Practice T est – 2A – KEY
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-­‐
methyloct-­‐4-­‐ene Cis-­‐2,3,4,5-­‐
tetramethylhept-­‐3-­‐ene 3-­‐ethyl-­‐2-­‐
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 Practice T est – 2A – KEY
7. Please identify whether the following reactions are addition, substitution, elimination or rearrangement. (3) Substitution Addition Rearrangement 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) Na2Cr2O7
H2
Pd Catalyst
Practice T est – 2A – KEY
9. Please provide all of the products, reactants, or starting material for the following reactions. If there is major product, please specify with a circle. (24) (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 of the products) Name: (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: Practice T est – 2B
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 Practice T est – 2B
7. Please complete the following table by providing the appropriate structure or name of the following compounds. (12) 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: Practice T est – 2B
10. 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. (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-­‐
methyl-­‐2-­‐petnene Name: 3-­‐chloro-­‐2-­‐
ethyl-­‐3-­‐methylpentane (8) HNO3
H2SO4 Catalyst
Name: 1,2-­‐dimethyl-­‐
3-­‐nitrobenzene Name: o-­‐Xylene (10) Br2
FeBr3
Name: 2,6-­‐dimethylbenzoic acid Name: 3-­‐bromo-­‐2,6-­‐
dimethylbenzoic acid Name: 4-­‐bromo-­‐2,6-­‐
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-­‐
trimethylhept-­‐3-­‐ene Name: Cis 3,4,5-­‐
trimethylhept-­‐3-­‐ene Practice T est – 2B – KEY
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-­‐
methylpentanethiol Name: 3-­‐methylpentane 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 Practice T est – 2B – KEY
7. Please complete the following table by providing the appropriate structure or name of the following compounds. (12) 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) 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) H2
Pd Catalyst
Type: Addition Name: 3-­‐ethyl-­‐7-­‐
methyl-­‐4-­‐nonyne (3) Type: Substitution Practice T est – 2B – KEY
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. (5) (5) Type: Elimination H2SO4
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