Alkynes. Amides. Aromatics. Hydration of Alkenes. Thiols Salts. Acetal Formation

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1 ` Learning Commons

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3 3 Alkynes Amides Aromatics ydration of Alkenes Thiols Salts Acetal Formation

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5 5 USER GUIDE 7 UNIT I 9 ACIDS & BASES ACIDS & BASE CEMISTRY GRAM EQUIVALENTS- NORMALITY- TITRATION P - PO [ ] [ - O] BUFFERS 19 ALKANES NAMING ALKANES FUNCTIONAL GROUPS DRAWING STRUCTURES CONFORMERS & ISOMERS 29 PRACTICE TESTS 1A 31 1B 39 UNIT II 47 ALKENES, ALKYNES & AROMATICS NAMING ALKENES, ALKYNES, & AROMATICS CIS/TRANS POLYMERS REACTIONS OF ALKENES, ALKYNES, & AROMATICS 57 ALCOOLS, PENOLS, ETERS, TIOLS, & ALOGENS NAMING ALCOOLS, PENOLS, ETERS, TIOLS, & ALOGENS REACTIONS OF ALCOOLS, PENOLS, ETERS, TIOLS, & ALOGENS 63 PRACTICE TESTS 2A 65 2B 73

6 UNIT III 81 AMINES, ALDEYDES, KETONES, CARBOXYLIC ACIDS, ESTERS, & AMIDES NAMING AMINES, ALDEYDES, & KETONES NAMING CARBOXYLIC ACIDS, ESTERS, & AMIDES REACTIONS TESTS (LUCAS, BENEDICTS, & TOLLENS) REACTIONS OF CARBONYLS 91 CARBOYDRATES CARBOYDRATE NOMENCLATURE REACTIONS OF CARBOYDRATES CONVERTING FISCER TO CYCLIC 99 PRACTICE TESTS 3A 101 3B 109 TOOLS 117 NOMENCLATURE 119 COMMON FUNCTIONAL GROUPS 120 SIGNIFICANT FIGURES 121 PERIODIC TABLE OF TE ELEMENTS 123

7 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. Worksheets: Ø 1 page of problems on a focused topic Ø FRONT = BLANK Ø BACK = ANSWER KEY Ø Print off/copy for student Ø Or work on with student Ø Consult textbook for detailed explanation of topic Practice Exams: Ø 3-4 pages of simulated exam type questions o There are two types of exams: A very similar to worksheets B more integrative concepts & analysis Ø TREAT IT LIKE A REAL EXAM o Grab a study carrel or another quite place o No drinks/food, cell phones, textbooks, or computers Ø Allow no more than minutes to complete. Ø Answer key immediately follows the blank test Ø Grade exam for students just like a professor would Ø Or grade exam with student learn from mistakes! NOTE: These worksheets and practice exams are intended to be used with a knowledgeable tutor and therefore, the most problems encountered are NOT meant to be easy. The theory: if a student can complete difficult practice problems with a tutor, they can excel independently on a standard exam level. 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 and much of this anxiety can be avoided by increased knowledge of material, as well as experience with testing environments. Once the student has completed an exam, the tutor may choose to grade the exam during a normal session while the student works on other materials (such as worksheets) and return the graded exam to the student. Alternatively, a tutor could evaluate the exam with the student. It is not advised, however, to simply provide the student with the answer key without a tutor to review the exam also. This is due the simple fact that it is hard to catch our own mistakes. Also, because the practice exam does not directly affect the student s course grade, the path of least resistance (neglecting to evaluate) is easy to be taken. The point of this book is to help identify problem areas and provide a means to address and remedy them. appy tutoring!

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11 83 Aldehydes Replace the e at the end of the parent chain with al. Ketones Replace the e at the end of the parent chain with one. Carboxylic Acids Replace the e at the end of the parent chain with oic acid. Esters 1 st the name of alkyl group off the ester. 2 nd the name of the parent acid, replacing ic by ate. Amines Count the # of carbons Compounds to MEMORIZE Amines Replace the e at the end of the parent chain with amine. Use a number to identify the location of the nitrogen, either before the parent name or before amine. The name of any alkyl group bonded to the nitrogen is preceded by an N. Amides 1 st name alkyl group off the amide preceding with N. 2 nd name parent acid, replacing ic with amide.

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13 Worksheet Naming Amines, Aldehydes, & ketones Please complete the following table by either providing the structure or the name of the compound. Formaldehyde N,N- diethyl- 5- fluoroheptan- 3- amine 2- chloro- 3- methylhexanal 3,4- diethyl- 3- methyl- 2- hexanone 5- bromo- 3- methylheptanal

14 3.1 Worksheet KEY Naming Amines, Aldehydes, & ketones Please complete the following table by either providing the structure or the name of the compound. Ethylpropylamine 4,4,- dimethylpentanal Acetone 3- methylcyclohexanone 2- ethyl- N- isopropyl- N- methylcyclohexanamine Formaldehyde N,N- diethyl- 5- fluoroheptan- 3- amine 2- chloro- 3- methylhexanal 5- bromo- 2- methyl- 4- heptanone 3,4- diethyl- 3- methyl- 2- hexanone Acetalaldehyde N- sec- butyl- 2- tert- butyl- N- isobutylcyclopentanamine 5- ethyl- 6- methyl- 4- octanone 3- chloro- 5- cyclobutylbenzaldehyde 5- bromo- 3- methylheptanal

15 3.2 Worksheet Naming Carboxylic Acids, Amides, & Esters Please complete the following table by either providing the structure or the name of the compound. 87 N,N,3- triethylpentanamide Butyl octanoate 3- cyclcohexyl- N- isopropyl- N,2,4- trimethyloctanamide 3- chloro- 4- cyclopropyl- 2- isopropylpentoic acid 4- ethyl- 5- methyl- N,N- dipropylheptanamide 2- ethyl- 6- iodo- 3,3- dimethylheptanoic acid

16 3.2 Worksheet KEY Naming Carboxylic Acids, Amides, & Esters Please complete the following table by either providing the structure or the name of the compound. Ethyl 3- methylpentanoate 4- fluoro- N- methyl- hexanamide 3- chlorobutanoic acid 4- methylpentanamide Pentyl 3- propyl- 6- bromohexanoate N,N,3- triethylpentanamide Butyl octanoate Butyl 3- bromo- 3- isobutylpentanoate 4- chloro- 3- propyl- 4- methylpentanoic acid Cyclopentyl 5- ethyl- 3- methyloctanoate 3- cyclcohexyl- N- isopropyl- N,2,4- trimethyloctanamide 3- chloro- 4- cyclopropyl- 2- isopropylpentoic acid 4- ethyl- 5- methyl- N,N- dipropylheptanamide 2- tert- butyl- 3- isopropylhexanoic acid 2- ethyl- 6- iodo- 3,3- dimethylheptanoic acid

17 3.3 Worksheet Reactions Tests (Lucas, Benedicts, & Tollens) 89 Please provide the name of the following tests as well as the reactants, products, or starting materials. Name: Name: A Lucas test is performed on the following alcohols to determine if the presence of a primary, secondary, or tertiary alcohol. Using your knowledge of the Lucas test please identify which alcohol is in which beaker. Beaker A: No precipitation after one hour Beaker B: Precipitation observed after four minutes Beaker C: Precipitation observed immediately Write the reaction that occurs in beaker C: Perform a Benedicts test on the following compound. Make sure to list all reagents and the expected products & colors associated. Perform a Tollens test on the following compound, make sure to list all reagents and the expected products & colors associated.

18 3.3 Worksheet KEY Reactions Tests (Lucas, Benedicts, & Tollens) Please provide the name of the following tests as well as the reactants, products, or starting materials. Name: Tollens Test Name: Benedicts Test A Lucas test is performed on the following alcohols to determine if the presence of a primary, secondary, or tertiary alcohol. Using your knowledge of the Lucas test please identify which alcohol is in which beaker. Beaker A: No precipitation after one hour (I) Beaker B: Precipitation observed after four minutes (III) Beaker C: Precipitation observed immediately (II) Write the reaction that occurs in beaker C: Perform a Benedicts test on the following compound. Make sure to list all reagents and the expected products & colors associated. Buffer Perform a Tollens test on the following compound, make sure to list all reagents and the expected products & colors associated. N 3 2O Ag(s)

19 3.4 Worksheet Reactions of Carbonyls 91 Please complete the following reactions by either providing the reactants, products or starting materials.

20 3.4 Worksheet KEY Reactions of Carbonyls Please complete the following reactions by either providing the reactants, products or starting materials. CN

21 93 D & L Sugars Look at last chiral carbon If hydroxyl is on right D Fischer à Cyclic RIGT in Fischer DOWN in Cyclic If hydroxyl is on the left L LEFT in Fischer UP in Cyclic # of Stereoisomers Compounds to MEMORIZE 2 n n = # of chiral carbons DISSACCARIDES to MEMORIZE

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23 3.5 Worksheet Carbohydrate Nomenclature 95 Please classify the following compounds through use of the terms aldose and ketose, including the # of carbons in the name. Classification: D or L: Classification: D or L: Please classify the following compounds through use of the terms aldose and ketose, including the # of carbons in the name. Also, draw its enantiomer and name both compounds including the appropriate D/L nomenclature. Classification: Original: Enantiomer: Classification: Original: Enantiomer: Classification: Original: Enantiomer: Please identify the following disaccharides, the two monomers that make up the disaccharides, and the types of glycosidic bonds between them. Name: Monomers: Type of Bond: Name: Monomers: Type of Bond: Please draw Maltose. Indicate the two monomers that make up the disaccharide as well as the type of bond between the two monomers. Briefly describe what amylose, amylopectin, and glycogen are and how amylopectin and glycogen are used in plants and animals.

24 3.5 Worksheet KEY Carbohydrate Nomenclature Please classify the following compounds through use of the terms aldose and ketose, including the # of carbons in the name. Classification: Aldopentose D or L: D Classification: Ketohexose D or L: L Please classify the following compounds through use of the terms aldose and ketose, including the # of carbons in the name. Also, draw its enantiomer and name both compounds including the appropriate D/L nomenclature. Classification: Aldopentose Original: D- Ribose Enantiomer: L- Ribose Classification: Aldohexose Original: D- Glucose Enantiomer: L- Glucose Classification: Ketohexose Original: D- Fructose Enantiomer: L- Fructose Please identify the following disaccharides, the two monomers that make up the disaccharides, and the types of glycosidic bonds between them. Name: Lactose Monomers: β- D- Galactose & D- Glucose Type of Bond: β- 1,4 Name: Cellobiose Monomers: β- D- Glucose & D- Glucose Type of Bond: β- 1,4 Please draw Maltose. Indicate the two monomers that make up the disaccharide as well as the type of bond between the two monomers. Briefly describe what amylose, amylopectin, and glycogen are and how amylopectin and glycogen are used in plants and animals. Amylose, amylopectin, and glycogen are all starches used for energy in living organisms. Amylopectin and glycogen also have α- 1,6 linkages which ultimately store more energy. Amylopectin does not have as frequent branching as glycogen. Due to the frequent branching, glycogen holds more potential for fast energy, which is why it is used in animals, whereas plants use amylopectin.

25 3.6 Worksheet Reactions of Carbohydrates Please complete the following reactions by providing the product(s), reactants, or the starting materials. 97 Working in a lab, your supervisor instructs you to perform both a Benedicts test and a Tollens test on fructose. You know that ketones have to undergo a rearrangement before they can be reduced. Please show the steps of the rearrangement then perform both tests with the appropriate reagents.

26 3.6 Worksheet KEY Reactions of Carbohydrates Please complete the following reactions by providing the product(s), reactants, or the starting materials. Working in a lab, your supervisor instructs you to perform both a Benedicts test and a Tollens test on fructose. You know that ketones have to undergo a rearrangement before they can be reducing sugars. Please show the steps of the rearrangement then perform both tests with the appropriate reagents. Benedicts Tollens

27 3.7 Worksheet Converting Fischer to Cyclic 99 Please convert the following from Fischer to cyclic form. O O O O O O Please convert the following from cyclic to Fischer.

28 3.7 Worksheet KEY Converting Fischer to Cyclic Please convert the following from Fischer to cyclic form. O O O O O O Please convert the following from cyclic to Fischer.

29 Practice Test 3A Please complete the following table by either providing the compound s structure or name. (30) 101 Isopropylisobutylamine Acetone Isobutyl 3- methylbutanoate N- sec- butylpropanamide 3- cyclopentyl- 4- methylhexanal Formaldehyde

30 Practice Test 3A 2. A Lucas test is performed on the following alcohols to determine if the presence of a primary, secondary, or tertiary alcohol. Using your knowledge of the Lucas test please identify which alcohol is in which beaker. (6) Beaker A: Precipitation observed immediately Beaker B: Precipitation observed after four minutes Beaker C: No precipitation after one hour Write the reaction that occurs in beaker A: 3. Please complete the following reactions either by providing the products, reactants, or starting materials. (16)

31 Practice Test 3A 103 Working in a lab, your supervisor instructs you to perform both a Benedicts test and a Tollens test the following ketohexose. You know that ketones have to undergo a rearrangement before they can be reducing sugars. Please show the steps of the rearrangement then perform both tests with the appropriate reagents. Also, please name the ketohexose. (12) Benedicts Tollens Name: Please classify and identify the following carbohydrates by name and provide their enantiomers structure and name. Be sure to include appropriate D or L specification. (8) Classification: Original: Enantiomer: Classification: Original: Enantiomer: Please identify the following disaccharides, the two monomers that make up the disaccharides, and the types of glycosidic bonds between them. (8) Name: Monomers: Type of Bond: Name: Monomers: Type of Bond:

32 Practice Test 3A 7. Briefly describe what amylose, amylopectin, and glycogen are and how amylopectin and glycogen are used in plants and animals. (4) 8. Please complete the following reactions, either by providing the products, reactants, or starting materials. Also, when prompted provide the name of the compound in question. (8) (6) Name of starting material(s): Name of product: (2) (4) 9. Please convert the following compound from Fischer to cyclic & provide its name. (4) O O O O O O Name of starting material: Name: 100

33 Practice Test 3A KEY 1. Please complete the following table by either providing the compound s structure or name. (30) chloro- 3- ethylpentanoic acid Propyl 2- bromopropanoate Isopropylisobutylamine Acetone 2,2- dimethyl- 3- ethylhexanal N- ethyl- 3- iodo- 2- propyl- N- methylpentanamide 4- ethyl- 6- fluoroheptan- 3- one N- tert- butyl- N- isopropyl- 2- methylcyclopentanamine Isobutyl 3- methylbutanoate N- sec- butylpropanamide Formic Acid 2,2,5,5- Tetrachloro- 3- ethylcyclohexanone 3- cyclopentyl- 4- methylhexanal 2- Iodo- 3- propyl- 2- methylhexanoic acid Formaldehyde

34 Practice Test 3A KEY 2. A Lucas test is performed on the following alcohols to determine if the presence of a primary, secondary, or tertiary alcohol. Using your knowledge of the Lucas test please identify which alcohol is in which beaker. (6) Beaker A: Precipitation observed immediately II Beaker B: Precipitation observed after four minutes I Beaker C: No precipitation after one hour III Write the reaction that occurs in beaker A: 3. Please complete the following reactions either by providing the products, reactants, or starting materials. (16)

35 Practice Test 3A KEY Working in a lab, your supervisor instructs you to perform both a Benedicts test and a Tollens test the following ketohexose. You know that ketones have to undergo a rearrangement before they can be reducing sugars. Please show the steps of the rearrangement then perform both tests with the appropriate reagents. Also, please name the ketohexose. (12) Benedicts O O Tollens O O O O O 5. Please classify and identify the following carbohydrates by name and provide their enantiomers structure and name. Be sure to include appropriate D or L specification. (8) (4) (4) Classification: Aldohexose Original: D- Galactose Enantiomer: L- Galactose Classification: Aldopentose Original: D- Ribose Enantiomer: L- Ribose 6. Please identify the following disaccharides, the two monomers that make up the disaccharides, and the types of glycosidic bonds between them. (8) (4) (4) Name: Sucrose Monomers: β- D- Fructose & D- Glucose Type of Bond: β- 1,2 Name: Maltose Monomers: β- D- Glucose & D- Glucose Type of Bond: α- 1,4

36 Practice Test 3A KEY 7. Briefly describe what amylose, amylopectin, and glycogen are and how amylopectin and glycogen are used in plants and animals. (4) Amylose, amylopectin, and glycogen are all starches used for energy in living organisms. Amylopectin and glycogen have α- 1,6 linkages which ultimately store more energy. Amylopectin does not have as frequent branching as glycogen. Due to the frequent branching, glycogen holds more potential for fast energy, which is why it is used in animals (fight/flight), whereas plants use amylopectin. 8. Please complete the following reactions, either by providing the products, reactants, or starting materials. Also, when prompted provide the name of the compound in question. (8) (6) Name of starting material(s): β- D- Galactose & D- Glucose Name of product: Lactose (2) O O O 3 C O O O C 3 (4) 9. Please convert the following compound from Fischer to cyclic & provide its name. (4) O O O O O O Name of starting material: D- Glucose Name: 2- D- deoxyribose

37 109 Practice Test 3B 1. Please complete the following reactions by either providing the starting materials, reactants, or product(s). When prompted, please provide the name of the compound in question. (24) (4) O (6) O O O Name: (8) O Name: Name: Name: Name: (6) Name: 2. Ketoses are reducing sugars because under certain conditions, they undergo a rearrangement that allows them to be reduced. Please show each step of this rearrangement with D- Fructose. Be sure to include any inorganic reagents needed, and please name the product. (8) Name:

38 Practice Test 3B 3. A test is performed on 2- chloro- 3- ethylpentanal that yields a silver precipitate. Please identify which test was performed as well as show this reaction including all starting materials, reactants, and products. (10) 4. In a lab, you have two unlabeled beakers containing either 3- ethylcyclohexanone or 2- isopropylbutanal. Using only a reduction reaction with NaB4 and a Lucas test, show the reactions that would help determine the identity of the two beakers. Be sure to include all starting materials, reactants, products, and to explain your deduction. (12) 5. A test was performed on D- Galactose that produced a red solution. Please identify which test was performed as well as show this reaction including all starting materials, reactants, and products. (10) 6. Please provide the cyclic structure of the starting materials and provide the reactants to this reaction involving α- D- Glucose. (4)

39 111 Practice Test 3B 7. Please complete the following table by providing either the name or the structure of the compound. (12) Acetic Acid O 2- fluoro- 4- methylpentaonic acid 8. Please classify the following compound as an aldose/ketose, D/L sugar, and then draw its enantiomer then and convert from the original Fischer structure to its cyclic form. (6) Enantiomer Cyclic Form Classification: D/L: 7. Briefly describe what amylose, amylopectin, and glycogen are and how amylopectin and glycogen are used in plants and animals. (4) 8. Please circle all of the chiral carbons and calculate the maximum # of stereoisomers possible. (4)

40 Practice Test 3B Please provide the structure for Lactose, identify the monomers that make up the disaccharide, and provide the type of bond between the two monomers. (6) 100

41 113 Practice Test 3B KEY 1. Please complete the following reactions by either providing the starting materials, reactants, or product(s). When prompted, please provide the name of the compound in question. (24) (4) O O (6) O O O O O O O Name: D- Ribose (8) O Name: Cyclopentyl 2,2- dimethylpropanoate Name: Ethyl propylamine (6) Name: 2- Chlorobutanoic acid Name: 2- Chloro- N- ethyl- N- propylbutanamide Name: 3- ethyl- 2- hexanone 2. Ketoses are reducing sugars because under certain conditions, they undergo a rearrangement that allows them to be reduced. Please show each step of this rearrangement with D- Fructose. Be sure to include any inorganic reagents needed, and please name the product. (8) Name: D- Glucose

42 Practice Test 3B KEY 3. A test is performed on 2- chloro- 3- ethylpentanal that yields a silver precipitate. Please identify which test was performed as well as show this reaction including all starting materials, reactants, and products. (10) Tollens Test 4. In a lab, you have two unlabeled beakers containing either 3- ethylcyclohexanone or 2- isopropylbutanal. Using only a reduction reaction with NaB4 and a Lucas test, show the reactions that would help determine the identity of the two beakers. Be sure to include all starting materials, reactants, products, and to explain your deduction. (12) Precipitate will form within 5 minutes No precipitate will form in an hour 5. A test was performed on D- Galactose that produced a red solution. Please identify which test was performed as well as show this reaction including all starting materials, reactants, and products. (10) O O O O O O D-Galactose 6. Please provide the cyclic structure of the starting materials and provide the reactants to this reaction involving α- D- Glucose. (4)

43 115 Practice Test 3B KEY 7. Please complete the following table by providing either the name or the structure of the compound. (12) N- ethyl- N- methylhexan- 3- amine Acetic Acid Ethyl 2- bromopropanoate O 2- fluoro- 4- methylpentaonic acid N,2- diethyl- N- methylbutanamide Formaldehyde 8. Please classify the following compound as an aldose/ketose, D/L sugar, and then draw its enantiomer then and convert from the original Fischer structure to its cyclic form. (6) Enantiomer Cyclic Form Classification: Ketohexose D/L: D 7. Briefly describe what amylose, amylopectin, and glycogen are and how amylopectin and glycogen are used in plants and animals. (4) Amylose, amylopectin, and glycogen are all starches used for energy in living organisms. Amylopectin and glycogen have α- 1,6 linkages which ultimately store more energy. Amylopectin does not have as frequent branching as glycogen. Due to the frequent branching, glycogen holds more potential for fast energy, which is why it is used in animals (fight/flight), whereas plants use amylopectin. 6 chiral centers à 2 6 = 64 possible stereoisomers

44 Practice Test 3B KEY Please provide the structure for Lactose, identify the monomers that make up the disaccharide, and provide the type of bond between the two monomers. (6) 1,4- β linkage 100

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