Experiment 8: Nucleophilic Substitution Reactions of Alkyl Halides

Size: px
Start display at page:

Download "Experiment 8: Nucleophilic Substitution Reactions of Alkyl Halides"

Transcription

1 Experiment 8: Nucleophilic Substitution Reactions of Alkyl Halides exp 1: Reaction with Sodium Iodide in Acetone exp 2: Reaction with Silver Nitrate in Ethanol Reading: Carey & Guiliano Ch. 8 pgs

2 Nucleophilic Substitution Important reaction of alkyl halides Two common mechanistic pathways: S N 1: substitution, nucleophilic, unimolecular RDS S N 2: substitution, nucleophilic, bimolecular RDS

3 Reaction Features S N 1 Reactions: - rate determining step involves ionizaton carbocation - reaction rate governed by cation stability - RX: 3 > 2 >> 1 S N 2 Reactions: - rate determining step involves backside attack of Nu - reaction rate governed by sterics - RX: 1 > 2 >> 3

4 Comparison: S N 1 vs. S N 2 S N 1 S N 2 intermediate mechanism kinetics nucleophile solvent rate determined by substrate stereochemistry rearrangements carbocation stepwise 1st order weak or strong polar, protic cation stability 3 > 2 > 1 retention & inversion common no formal intermediate concerted 2nd order strong various sterics CH 3 X > 1 > 2 > 3 inversion not possible

5 Next Week (November 7-11) Experiment 8: Nucleophilic Substitution Reactions of R-X A. NaI in Acetone reaction via S N 2 mechanism B. AgNO 3 in ethanol reaction via S N 1 mechanism NOTE: We will not do concentration studies for either part DUE: Alkyne Synthesis Lab Report (exp 7) Lab Reports are due at the beginning of your regular lab session

6 Substrates

7 Reactions NaI in acetone (S N 2) - I - is a very good nucleophile - acetone is a polar, aprotic solvent - reaction will result in precipitate formation (NaCl or NaBr) AgNO 3 in ethanol or ethanol/water (S N 1) - Ag + in protic solvent - rapidly generates R + and AgX (ppt) formation of ppt tells you reaction has occurred - subsequent reaction of R + with solvent (ethanol), etc.

8 Determine Characteristics of Nu Substitution Evaluate the reactivity of the alkyl halide substrates considering: - primary structure (1, 2, 3 ) - secondary structure (steric effects, proximity of double bonds) - nature of the leaving group (Br vs Cl) - concentration (substrate vs. reagent) - should understand - solvent (S N 1 vs S N 2 reaction) - reaction temperature (will evaluate indirectly) Qualitative evaluation - be ready to observe and record your results - watch for ppt formation - no products will be isolated - no yield will be determined

9 Experimental Details - NaI in acetone (S N 2) 1. Obtain microtubes & corks (8-10 each) - be sure tubes are clean & dry 2. Add 15% NaI/acetone (2 ml) to reaction tubes - more is not better 3. Add substrates to reaction tubes - 2 drops of substrate per reaction tube (~ 0.1 ml) - one substrate per tube - be sure to label them so you know what is in each one! - immediately stopper tubes, mix thoroughly, note start time - watch for ppt formation at room temperature record the exact time for ppt formation (if any) in each tube try to quantify how much ppt forms (a lot? just a little?) also record observations when no ppt forms 4. If no precipitate forms after ~ 5 minutes, heat to 50 C in hot water bath - note start time - watch for reaction (ppt formation) over next 4-5 minutes - record observations (e.g. reaction time; quantity of precipitate)

10 Experimental Details - NaI in acetone (S N 2) Specific Experiments: 1. Primary Structure - substrates: - expectations?: 1 > 2 >> 3 >>>> aryl 2. Secondary Structure - substrates: - expectations?: allylic > 1 unhindered > hindered

11 Experimental Details - NaI in acetone (S N 2) Specific Experiments (cont): 3. Leaving Group - substrates: - expectations?: Br > Cl (Br better able to accommodate negative charge) 4. Concentration (NOTE: we will not do this portion of the experiment) - substrate: - variations: change substrate concentration change Nu concentration - expectations?: both situations will result in an increase in reaction rate specifically, expect rate to double in each case because the reaction is bimolecular! k = [RX][I - ]

12 Experimental Details - AgNO 3 in ethanol (S N 1) 1. Empty microtubes from last set of reactions & wash with ethanol - DO NOT use acetone! 2. Add 1% AgNO 3 /ethanol (1 ml) to reaction tubes - more is not better 3. Add substrates to reaction tubes - 2 drops of substrate per reaction tube (~ 0.1 ml) - one substrate per tube (be sure you know what's in each one!) - immediately stopper tubes, mix thoroughly, note start time - watch for ppt formation at room temperature record the exact time for ppt formation (if any) in each tube try to quantify how much ppt forms (a lot? just a little?) also record observations when no ppt forms 4. If no precipitate forms after ~ 5 minutes, heat to 50 C in hot water bath - note start time - record observations as before 5. When finished, wash tubes (rinse well!), dry, & return - PLEASE do not put them in your drawer!

13 Experimental Details - AgNO 3 in ethanol (S N 1) Specific Experiments: 1. Primary Structure - substrates: - expectations?: 3 > 2 >> 1 >>>> aryl 2. Secondary Structure - substrates: - expectations?: allylic > 1 why??

14 Experimental Details - AgNO 3 in ethanol (S N 1) Specific Experiments (cont): 3. Leaving Group - substrates: - expectations?: Br > Cl (Br better able to accommodate negative charge) 4. Concentration (NOTE: we will not do this portion of the experiment) - substrate: - variations: double substrate concentration double Nu concentration - expectations?: double [RX], expect reaction rate to double double [Nu], expect no change because the reaction is unimolecular! k = [RX]

15 Experimental Details - AgNO 3 in ethanol (S N 1) Specific Experiments (cont): 5. Solvent - substrate: - variations: ethanol ethanol/water - expectations?: rxn in ethanol/water will be faster both are polar, protic solvents (favor S N 1) pure water has a higher dielectric constant = more polar (really favors S N 1)

16 Writing the Lab Report: Exp #8 Alkyne Synthesis Purpose - what will you make? - include a balanced chemical equation for every reaction you did Results & Discussion - Comment on the success of your reaction sequence Did each step work? How do you know? physical appearance, TLC & melting point don t forget to discuss the changes in Rf values that you observe - Were the products pure? How do you know? TLC & mp data Was your recrystallization successful for step 2? - Was the reaction sequence efficient? Calculate the % yield for each step Calculate the overall yield

17 Writing the Lab Report: Exp #8 Alkyne Synthesis Conclusion - a brief recap of your findings - was your reaction sequence successful (did you make it? was it pure?) - do not include theory Appendix A: Calculations - Table of reagents (for each step) - Determine the limiting reagent (for each step) - Percent Yield calculation (for each step) for step 2, keep in mind you may not have recrystallized everything see page 91 of the lab manual for details - Overall Yield calculation example follows - Rf calculation Appendix B: Spectra - none

18 Calculating Overall Yield: Reaction Sequence: 1. Calculate yield for each step (as discussed last week) 87% 94% 2. Multiply individual yields together Overall Yield = (yield step 1 ) x (yield step 2 )... x 100 = (0.87) x (0.94) x 100 = 82%

EXPERIMENT 8 RELATIVE RATES OF NUCLEOPHILIC SUBSTITUTION REACTIONS

EXPERIMENT 8 RELATIVE RATES OF NUCLEOPHILIC SUBSTITUTION REACTIONS EXPERIMENT 8 RELATIVE RATES OF NUCLEOPHILIC SUBSTITUTION REACTIONS Reading Assignment: Smith, Chapter 7 Pre-lab Questions: 1) What determines whether 2-bromobutane undergoes an S N 1 or an S N 2 reaction?

More information

Chemistry C Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations. Nucleophilic Substitution

Chemistry C Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations. Nucleophilic Substitution Chemistry 201 - C Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations This presentation was created by Professor Carl H. Snyder Chemistry Department University of Miami Coral Gables,

More information

Willem Elbers. October 9, 2015

Willem Elbers. October 9, 2015 S N 1 and S N 2 reactivity of 3 alkyl bromides Willem Elbers ctober 9, 2015 1 Abstract n this experiment, we investigate the relative reactivities of three alkyl bromides with increasing steric bulk. We

More information

7.1 Introduction to Substitution Reactions. 7.1 Introduction to Substitution Reactions. Reactions. 7.2 Alkyl Halides. Reactions

7.1 Introduction to Substitution Reactions. 7.1 Introduction to Substitution Reactions. Reactions. 7.2 Alkyl Halides. Reactions 7.1 Introduction to Substitution Reactions One group of atoms is replaced with another. Generic example: 7.1 Introduction to Substitution Reactions Which side do you think will be favored in the dynamic

More information

CHEMICAL REACTIVITY AND MECHANISMS, AND SUBSTITUTION REACTIONS

CHEMICAL REACTIVITY AND MECHANISMS, AND SUBSTITUTION REACTIONS EMIAL REATIVITY AND MEANISMS, AND SUBSTITUTION REATIONS A STUDENT SOULD BE ABLE TO: 1. Understand the concepts of: enthalpy, entropy, free energy, equilibrium and kinetics. Given a reaction coordinate

More information

Nucleophilic Substitution and Elimination Reaction

Nucleophilic Substitution and Elimination Reaction Dr. Keshar Prasain Nucleophilic Substitution and Elimination Reaction After the completion of this chapter students should be familiar with substitution and elimination reactions, know the mechanism of

More information

Chapter 6 Ionic Reactions-Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Chapter 6 Ionic Reactions-Nucleophilic Substitution and Elimination Reactions of Alkyl Halides Chapter 6 Ionic Reactions-Nucleophilic Substitution and Elimination Reactions of Alkyl alides Introduction The polarity of a carbon-halogen bond leads to the carbon having a partial positive charge In

More information

Experiment 7: Synthesis of an Alkyne from an Alkene

Experiment 7: Synthesis of an Alkyne from an Alkene Experiment 7: Synthesis of an Alkyne from an Alkene Synthesis of an Alkyne from an Alkene This week's synthesis: step 1: Part A: Synthesis of meso-stilbene dibromide Part B: Synthesis of diphenylacetylene

More information

Lecture Notes Chem 51B S. King. Chapter 8 Alkyl Halides and Elimination Reactions

Lecture Notes Chem 51B S. King. Chapter 8 Alkyl Halides and Elimination Reactions Lecture Notes hem 51B S. King hapter 8 Alkyl alides and Elimination Reactions The characteristic reactions of alkyl halides are nucleophilic substitution and elimination. I. Nucleophilic Substitution:

More information

Sn1 REACTINS From a synthetic point of view, the Sn1 reaction is less useful. It is prone to side reactions such as eliminations and carbocation rearr

Sn1 REACTINS From a synthetic point of view, the Sn1 reaction is less useful. It is prone to side reactions such as eliminations and carbocation rearr IGLIGTS F NUCLEPILIC SUBSTITUTIN REACTINS INVLVING sp3 CARBN Nu + C L C Nu + L Nucleophile Electrophile, or substrate L= leaving group Nucleophilic substitution product Sn2 REACTINS From a synthetic point

More information

Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations SHORT ANSWER Exhibit 11-1 Circle your response in each set below. 1. Circle the least

More information

CHP 8 Questions , 33, 35, Nucleophilic Substitution Reactions

CHP 8 Questions , 33, 35, Nucleophilic Substitution Reactions CHP 8 Questions 8.1-31, 33, 35, 40-42. 8. Nucleophilic Substitution Reactions 8.1 The General Reaction In the reaction of chloromethane with hydroxide ion the hydroxide ion is substituted for the chlorine

More information

MCAT Organic Chemistry - Problem Drill 20: Mechanisms of Organic Reactions

MCAT Organic Chemistry - Problem Drill 20: Mechanisms of Organic Reactions MCAT rganic Chemistry - Problem Drill 20: Mechanisms of rganic Reactions Question No. 1 of 10 Question 1. What does the arrow shown indicate in a mechanism? Question #01 (A) Movement of a pair of electrons

More information

2. Determine the product that would be formed from the S N 2 reaction of a. (R)-2-bromobutane and hydroxide ion (aprotic solvent) (S)-2-butanol

2. Determine the product that would be formed from the S N 2 reaction of a. (R)-2-bromobutane and hydroxide ion (aprotic solvent) (S)-2-butanol 1. Define and understand the following terms. (I will go over these if you have questions, but will expect that you have attempted to understand them on your own.) a. yperconjugation b. Basicity c. Nucleophile

More information

Where R = alkyl group, Nu = nucleophile and L = leaving group.

Where R = alkyl group, Nu = nucleophile and L = leaving group. Organic Chemistry (CEM311) Fall 2005 Dr. Robert F. Dias 9. SUBSTITUTIONS: S N 1, S N 2 2 basic kinds of substitution reactions: S N 2 = Substitution Nucleophillic Bimolecular S N 1 = Substitution Nuclophillic

More information

Chemistry 220 Organic Chemistry I Answers to Review Questions on Mechanisms

Chemistry 220 Organic Chemistry I Answers to Review Questions on Mechanisms Chemistry 220 rganic Chemistry Answers to Review Questions on Mechanisms 1. Write the structure of the principle organic product to be expected from the reaction of 1-bromopropane with each of the following

More information

Nucleophilic Substitution and Elimination

Nucleophilic Substitution and Elimination Nucleophilic Substitution and Elimination What does the term "nucleophilic substitution" imply? A nucleophile is an the electron rich species that will react with an electron poor species A substitution

More information

ORGANIC CHEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions

ORGANIC CHEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions ORGANIC CEMISTRY I PRACTICE EXERCISE Sn1 and Sn2 Reactions 1) Which of the following best represents the carbon-chlorine bond of methyl chloride? d d - d - d d d d - d - I II III IV V 2) Provide a detailed,

More information

RELATIONSHIP BETWEEN Sn1 and E1 REACTIONS. SYNTHETIC DRAWBACKS OF Sn1 REACTIONS

RELATIONSHIP BETWEEN Sn1 and E1 REACTIONS. SYNTHETIC DRAWBACKS OF Sn1 REACTIONS RELATIONSIP BETWEEN Sn1 and E1 REACTIONS SYNTETIC DRAWBACKS OF Sn1 REACTIONS In terms of synthetic value, any reactions whose mechanism involves carbocation formation suffer from some drawbacks. Once formed,

More information

Chapter 9 The Chemistry of Alkyl Halides

Chapter 9 The Chemistry of Alkyl Halides Instructor Supplemental Solutions to Problems 2010 Roberts and Company Publishers Chapter 9 The Chemistry of Alkyl Halides 9.1 (b) The product is ethylammonium iodide. Solutions to In-Text Problems 9.2

More information

Elimination Reactions

Elimination Reactions Elimination Reactions Just as there are two mechanisms of substitution (S N 2 and S N 1), there are two mechanisms of elimination (E2 and E1). E2 mechanism bimolecular elimination E1 mechanism unimolecular

More information

Chapter 6: Nucleophilic Substitution

Chapter 6: Nucleophilic Substitution Chapter 6: Nucleophilic Substitution 1. Identify the nucleophile in the following reaction. A) CH 3 Br B) OH C) H 2 O D) Br 2. Identify the leaving group in the following reaction. A) CH 3 CH 2 Br B) HS

More information

Alkyl Halides. Alkyl halides are a class of compounds where a halogen atom or atoms are bound to an sp 3 orbital of an alkyl group.

Alkyl Halides. Alkyl halides are a class of compounds where a halogen atom or atoms are bound to an sp 3 orbital of an alkyl group. Alkyl Halides Alkyl halides are a class of compounds where a halogen atom or atoms are bound to an sp 3 orbital of an alkyl group. CHCl 3 (Chloroform: organic solvent) CF 2 Cl 2 (Freon-12: refrigerant

More information

From alkanes Radical halogenation

From alkanes Radical halogenation From alkanes Radical halogenation 4 2 300 or h! Alkyl alides from Alkanes 3 form, where comes from 2 form, where comes from methane and comes from 2 break bond break bond what is the role of heating or

More information

Chemistry 307 Chapter 7

Chemistry 307 Chapter 7 Organic hemistry Nucleophilic Substitution. D. Roth hemistry 307 hapter 7 When we discussed the S N 2 reaction, we had considered two possible mechanisms, involving either a single step (nucleophilic substitution

More information

6.15 Organic Synthesis: Functional Group Transformations Using S N 2 Reactions

6.15 Organic Synthesis: Functional Group Transformations Using S N 2 Reactions 6.15 Organic Synthesis: Functional Group Transformations Using S N 2 Reactions S N 2 reactions are highly useful in organic synthesis because they enable use to convert one functional group into another

More information

Chapter 8 Nucleophilic Substitution

Chapter 8 Nucleophilic Substitution . 8 hapter 8 Nucleophilic ubstitution In this chapter we re-examine nucleophilic substitution reactions in more detail, paying particular attention to stereochemistry and other details of the reaction

More information

Chapter 8 Elimination

Chapter 8 Elimination Chapter 8 Elimination Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai i Prepared by Layne A. Morsch The University of Illinois - Springfield Modified and Used for Basic Org

More information

Alkyl Halides and Elimination Reactions. Alkyl Halides and Elimination Reactions

Alkyl Halides and Elimination Reactions. Alkyl Halides and Elimination Reactions General Features of Elimination Elimination reactions involve the loss of elements from the starting material to form a new π bond in the product. General Features of Elimination Equations [1] and [2]

More information

EXPERIMENT 4: Alkenes Preparations and Reactions

EXPERIMENT 4: Alkenes Preparations and Reactions EXPEIMENT 4: Alkenes Preparations and eactions elevant Sections in the text (Wade, 7 th ed.) 11.10 (p. 484) Dehydration reactions of alcohols 8.2 (p. 324), 8.8 (p. 344), 8.14 (p. 360) Electrophilic addition

More information

SUBSTITUTION REACTION CHARACTERISTICS. Sn1: Substitution Nucleophilic, Unimolecular: Characteristics

SUBSTITUTION REACTION CHARACTERISTICS. Sn1: Substitution Nucleophilic, Unimolecular: Characteristics SUBSTITUTION EATION AATEISTIS Sn2: Substitution cleophilic, Bimolecular: haracteristics 1) The 2 means Bimolecular (or 2 nd order) in the rate-determining (slow) step: rate = k [: - ] [-X] or rate = k

More information

CHM 226 Reducing Benzil

CHM 226 Reducing Benzil In this experiment, you will be reducing carbonyl groups on the compound benzil with sodium borohydride. In general chemistry, you learned about redox reactions in terms of the transfer of electrons; however,

More information

REACTION AND SYNTHESIS REVIEW

REACTION AND SYNTHESIS REVIEW REACTION AND SYNTHESIS REVIEW A STUDENT WHO HAS MASTERED THIS MATERIAL SHOULD BE ABLE TO PREDICT PRODUCTS, IDENTIFY REACTANTS, GIVE REACTION CONDITIONS, PROPOSE SYNTHESES, AND PROPOSE MECHANISMS (AS LISTED

More information

ANION ANALYSIS OBJECTIVES FOR THE EXPERIMENT

ANION ANALYSIS OBJECTIVES FOR THE EXPERIMENT 319 ANION ANALYSIS OBJECTIVES FOR THE EXPERIMENT The student will be able to do the following: 1. Write a general description of the qualitative analysis technique for identification of unknown substances.

More information

Core practical 4: Investigate the hydrolysis of halogenoalkanes

Core practical 4: Investigate the hydrolysis of halogenoalkanes Core practical 4 Teacher sheet Core practical 4: To investigate the relative rates of hydrolysis of, secondary and tertiary Obtain hot water from a kettle rather than using a naked flame in the laboratory.

More information

Key words: reaction mechanism, intermediates, kinetic studies, trapping of intermediates, rate of reaction

Key words: reaction mechanism, intermediates, kinetic studies, trapping of intermediates, rate of reaction Key words: reaction mechanism, intermediates, kinetic studies, trapping of intermediates, rate of reaction Introduction Reaction mechanism is a step by step description of a sequence of elementary reactions

More information

CHM220 Nucleophilic Substitution Lab. Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon*

CHM220 Nucleophilic Substitution Lab. Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon* CHM220 Nucleophilic Substitution Lab Studying S N 1 and S N 2 Reactions: Nucloephilic Substitution at Saturated Carbon* Purpose: To convert a primary alcohol to an alkyl bromide using an S N 2 reaction

More information

Reactions of Alkyl Halides. 1. The S N 2 reaction + OH HO

Reactions of Alkyl Halides. 1. The S N 2 reaction + OH HO Reactions of Alkyl alides This is probably the most confusing chapter in the first semester of organic chemistry, the reactions of alkyl halides. Alkyl halides undergo two basic types of reactions in organic

More information

Reactions in Organic Compounds. electrophile LUMO reaction

Reactions in Organic Compounds. electrophile LUMO reaction OMO Reactions in Organic Compounds As we first learned with acid/base reactions with Lewis definition, any reaction can be considered as a nucleophile reacting with an electrophile The closer in energy

More information

Homework Chapter 18 Ethers and Epoxides; Thiols and Sulfides

Homework Chapter 18 Ethers and Epoxides; Thiols and Sulfides Homework Chapter 18 Ethers and Epoxides; Thiols and Sulfides Problems with yellow highlight are mandatory homework; the rest are optional but recommended. Drawing Instructions: Draw structures corresponding

More information

The Behavior of Two Families in the Periodic Table

The Behavior of Two Families in the Periodic Table The Behavior of Two Families in the Periodic Table The Periodic Table arranges the elements in order of increasing atomic number in horizontal rows of such length that elements with similar properties

More information

ELIMINATION REACTIONS: E2 and E1

ELIMINATION REACTIONS: E2 and E1 ELIMINATION REACTIONS: E2 and E1 Chem 14D Winter 2006 Credit to Professor Steven Hardinger s Chemistry 14D Thinkbook (Winter 2006, blue version) and Paula Bruice s Organic Chemistry (4 th edition) from

More information

Ozonolysis of Alkenes

Ozonolysis of Alkenes zonolysis of Alkenes 1 When 2-methyl-2-pentene reacts with ozone, the initial 1,2,3-trioxolane product is 144, but this rearranges to ozonide 145. If 145 is treated with hydrogen peroxide as above, one

More information

Chapter 11 Alcohols and Ethers

Chapter 11 Alcohols and Ethers Nomenclature of Alcohols Systematic names Chapter 11 Alcohols and Ethers 1. Select the longest chain containing the hydroxyl and change the suffix ending of the parent alkane from -e to -ol 2. Number the

More information

Observing Equilibrium Shifts

Observing Equilibrium Shifts Cautions HCl is corrosive and toxic and acetone is flammable Purpose To demonstrate the different factors that affect equilibrium and explain the changes in terms of Le Chatelier s principle. Introduction

More information

Chemistry 3012 Foundational Chemistry Laboratory Manual

Chemistry 3012 Foundational Chemistry Laboratory Manual Chemistry 3012 Foundational Chemistry Laboratory Manual Table of Contents Page Experiment 1. Experiment 2. Experiment 3. Experiment 4. Experiment 5. Experiment 6. Experiment 7. Experiment 8. Determining

More information

ORGANIC CHEMISTRY I PRACTICE EXERCISE Elimination Reactions and Alkene Synthesis

ORGANIC CHEMISTRY I PRACTICE EXERCISE Elimination Reactions and Alkene Synthesis RGANIC CEMISTRY I PRACTICE EXERCISE Elimination Reactions and Alkene Synthesis ) ne of the products that results when -bromo-,-dimethylcyclopentane is heated in ethanol is shown below. Give a mechanism

More information

Experiment 6: Dehydration of 2-Methylcyclohexanol

Experiment 6: Dehydration of 2-Methylcyclohexanol Experiment 6: Dehydration of 2-Methylcyclohexanol Reading: Mohrig, Hammond & Schatz Ch. 19 pgs 256-276 Carey & Guiliano Ch. 5 pgs 184-207 Ch. 6 pgs 250-253 Dehydration of 2-Methylcyclohexanol This week's

More information

CSUS Department of Chemistry Experiment 11 Chem. 1A

CSUS Department of Chemistry Experiment 11 Chem. 1A Experiment 11. Qualitative Analysis of Ions Pre Laboratory Assignment Name: Lab Section 1. The elements in group IA belong to the alkali metal family. You have been given aqueous test solutions of 1 M

More information

ALKENES STRUCTURE, PROPERTIES, AND SYNTHESIS

ALKENES STRUCTURE, PROPERTIES, AND SYNTHESIS ALKENES STRUCTURE, PROPERTIES, AND SYNTESIS A STUDENT SOULD BE ABLE TO: 1. Give the IUPAC name when given the structure, and draw the structure given the name of open-chain alkenes using the E-Z system

More information

experiment5 Understanding and applying the concept of limiting reagents. Learning how to perform a vacuum filtration.

experiment5 Understanding and applying the concept of limiting reagents. Learning how to perform a vacuum filtration. 81 experiment5 LECTURE AND LAB SKILLS EMPHASIZED Synthesizing an organic substance. Understanding and applying the concept of limiting reagents. Determining percent yield. Learning how to perform a vacuum

More information

Organic Chemistry Practice Questions for Exam #2

Organic Chemistry Practice Questions for Exam #2 Organic hemistry 32-235 Practice Questions for Exam #2 Part 1: (ircle only ONE choice, circling more than one will be counted as wrong!) 4 points each 1. The correct IUPA name for the following compound

More information

2. Predict the MAJOR product IF the following reaction went by the S N 1 pathway: 3. Indicate the expected MAJOR product of the following reaction:

2. Predict the MAJOR product IF the following reaction went by the S N 1 pathway: 3. Indicate the expected MAJOR product of the following reaction: Quiz 4 Chem 109a [10%] of grade. NOTE: C-D bonds are stronger than C-H bonds...ie. harder to break. This is a very useful fact to know in some of the following questions. 1. Which of the following would

More information

Chapter 6: Chemical Reactivity and Mechanisms

Chapter 6: Chemical Reactivity and Mechanisms Chapter 6: Chemical Reactivity and Mechanisms Learning Objectives: Discover the details of writing reactions in organic chemistry Understand the arrows used in organic chemistry Explore the energy concepts

More information

Lecture and Lab Skills Emphasized Synthesizing an organic substance. Understanding and applying the concept of limiting reagents.

Lecture and Lab Skills Emphasized Synthesizing an organic substance. Understanding and applying the concept of limiting reagents. E x p e r i m e n t Synthesis of Aspirin Lecture and Lab Skills Emphasized Synthesizing an organic substance. Understanding and applying the concept of limiting reagents. Determining percent yield. Learning

More information

The concentration of starting materials and products are related to one another by the equilibrium constant, K, which is given by:

The concentration of starting materials and products are related to one another by the equilibrium constant, K, which is given by: EQUILIBRIA 8.1. Definitions. By convention, we write and read chemical equations left to right. Thus, starting materials are written to the left of reaction products. Let s look for example at a reaction

More information

Physical Properties, Chemical tests and Infrared Spectroscopy to Identify: (alkane, alkene, aromatic) (primary, secondary, tertiary)

Physical Properties, Chemical tests and Infrared Spectroscopy to Identify: (alkane, alkene, aromatic) (primary, secondary, tertiary) Physical Properties, Chemical tests and Infrared Spectroscopy to Identify: Unknown Halide Hydrocarbon Alcohol (primary, secondary, tertiary) (alkane, alkene, aromatic) (primary, secondary, tertiary) References:

More information

Chapter 7 Substitution Reactions

Chapter 7 Substitution Reactions Chapter 7 Substitution Reactions Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 7. Each of the sentences below appears

More information

Solubility and Qualitative Analysis

Solubility and Qualitative Analysis Lab 2 Name Solubility and Qualitative Analysis Experimental Questions How can solutions containing a mixture of ions be analyzed using solubility tests? Learning goals Review Lewis structures, polarity,

More information

CH421 Experiment 6. The Aldol Condensation: Synthesis of a Chalcone

CH421 Experiment 6. The Aldol Condensation: Synthesis of a Chalcone CH421 Experiment 6 The Aldol Condensation: Synthesis of a Chalcone Reading: Organic Chemistry by John McMurry, 8e, Chapter Sections 11.10 (E1cB mechanism) and 23.1 23.5 (Aldol condensation) Techniques:

More information

Preparation of an Alkyl Halide

Preparation of an Alkyl Halide Preparation of an Alkyl Halide onversion of a 3 o Alcohol to 3-hloro-3,7-dimethyloctane Nucleophilic Substitution, S N Nu: + L S N Nu + L: Substitution of one group for another at an sp 3 hybridized carbon

More information

Experiment 7A The Synthesis of Artificial Hyacinth Odor (1-bromo-2-phenylethene), Part I

Experiment 7A The Synthesis of Artificial Hyacinth Odor (1-bromo-2-phenylethene), Part I Experiment 7A The Synthesis of Artificial yacinth Odor (1-bromo-2-phenylethene), Part I This two-step synthesis involves the following conversion: trans-cinnamic acid 2,3- dibromocinnamic acid 1-bromo-2-phenylethene

More information

DEPARTMENT OF CHEMISTRY & CHEMICAL TECHNOLOGY

DEPARTMENT OF CHEMISTRY & CHEMICAL TECHNOLOGY DEPARTMENT OF CHEMISTRY & CHEMICAL TECHNOLOGY FINAL EXAMINATION CHEMISTRY 202-BZF-05 Monday, December 13, 2010 2:00 PM - 5:00 PM Name: SOLUTION Student Number: Final Examination Rules Before you begin

More information

c.(15) Rank the following compounds by anion stability. The most stable anion is 1 while the least stable anion is 5.

c.(15) Rank the following compounds by anion stability. The most stable anion is 1 while the least stable anion is 5. 1. Rank the following series by the trend requested. a.(15) Rank the following compounds by rate of S N 1 reactivity. Molecule that will react the fastest in an S N 1 reaction is 1 while the slowest is

More information

ORGANIC II LABORATORY(Major's) Aldehydes and Ketones

ORGANIC II LABORATORY(Major's) Aldehydes and Ketones GANIC II LABATY(Major's) KELLY EAD: Landgrebe pp 542-546 Aldehydes and Ketones I. Introduction Aldehydes and ketones are two of several types of compounds that contain the carbonyl group. eactions that

More information

Chapter 27 Answers. Practice Examples. (b) rearrangement (c) addition. (a) elimination (b) substitution (c) substitution.

Chapter 27 Answers. Practice Examples. (b) rearrangement (c) addition. (a) elimination (b) substitution (c) substitution. Chapter 27 Answers Practice Examples 1A 1B 2A (a) substitution rearrangement addition (a) elimination substitution substitution (a) 2B (a) 3A (a) CH 3 C C + CH 3 Br S N 2 CH 3 C CCH 3 + Br no reaction

More information

Periodic Properties of the Alkaline Earths and Halogens

Periodic Properties of the Alkaline Earths and Halogens Periodic Properties of the Alkaline Earths and Halogens Introduction Your team of research scientists have been hired as consultants by the Big Bubbly Bath Corporation or BBBC. Their problem is that a

More information

Nitration of Methyl Benzoate

Nitration of Methyl Benzoate Experiment 9 Nitration of Methyl Benzoate Objectives 1) To prepare methyl nitrobenzoate by electrophilic aromatic substitution reactions. 2) To demonstrate the regiochemistry of electrophilic aromatic

More information

COPYRIGHT FOUNTAINHEAD PRESS

COPYRIGHT FOUNTAINHEAD PRESS Stoichiometry of Lead Iodide: A Mole Ratio Study Objectives: To investigate the stoichiometry of the potassium iodide lead nitrate system in water. The volumes of reagents will be varied, and the mass

More information

Organic Chemistry Laboratory 2230 Final Exam Study Guide

Organic Chemistry Laboratory 2230 Final Exam Study Guide Organic Chemistry Laboratory 2230 Final Exam Study Guide Many students do not adequately prepare for the final exam in 2230L.The average grade is typically in the mid to upper 60 s. Each semester, some

More information

Purification by Recrystallization

Purification by Recrystallization Experiment 2 Purification by Recrystallization Objectives 1) To be able to select an appropriate recrystallizing solvent. 2) To separate and purify acetanilide by recrystallization. 3) To compare the melting

More information

Three Dimensional Reaction Coordinates of Nucleophilic Substitution Reactions

Three Dimensional Reaction Coordinates of Nucleophilic Substitution Reactions Southern Illinois University Carbondale OpenSIUC 2015 Emma Smith Hough Library Research Scholarship Awards 2014 Three Dimensional Reaction Coordinates of Nucleophilic Substitution Reactions Nathan D. Colley

More information

Chemistry 1215 Experiment #10 The Reaction of Zinc and Iodine: The Combination of Two Elements

Chemistry 1215 Experiment #10 The Reaction of Zinc and Iodine: The Combination of Two Elements Chemistry 1215 Experiment #10 The Reaction of Zinc and Iodine: The Combination of Two Elements Objective The objective of this experiment is to perform a combination reaction by reacting elemental zinc

More information

CHM 226 Suzuki Reaction

CHM 226 Suzuki Reaction INTRODUCTION Reactions that form carbon-carbon (C-C) bonds are very important because C-C bonds are the primary framework of all organic molecules. The Suzuki reaction is one of the most popular types

More information

EXPERIMENT 9: SOLUBILITIES

EXPERIMENT 9: SOLUBILITIES EXPERIMENT 9: SOLUBILITIES Pre-lab Questions: Answer these questions before coming to class. They introduce you to several important ideas that you will use in this experiment. You must turn-in this exercise

More information

Expt #4 - Properties of Aldehydes, Ketones, Carboxylic Acids, and Amines Acid/Base and Redox Reactions

Expt #4 - Properties of Aldehydes, Ketones, Carboxylic Acids, and Amines Acid/Base and Redox Reactions EXPERIMENT 4 Expt #4 - Properties of Aldehydes, Ketones, Carboxylic Acids, and Amines Acid/Base and Redox Reactions Materials Needed cyclohexanone, acetone, benzaldehyde, benzoic acid, acetic acid, cyclohexylamine

More information

Reactions of Nucleophiles and Bases. (b) at sp 2 centers (c) aromatic substitution

Reactions of Nucleophiles and Bases. (b) at sp 2 centers (c) aromatic substitution Chapter 3 Reactions of Nucleophiles and Bases 1) Nucleophilic substitution (a) at sp 3 2) Eliminations (a) E2 (b) Ei (b) at sp 2 centers (c) aromatic substitution 3) Nucleophilic addition to carbonyl compounds

More information

Chapter 11 Alkynes 1

Chapter 11 Alkynes 1 Chapter 11 Alkynes 1 Alkynes Introduction Structure and Bonding Alkynes contain a carbon carbon triple bond. Terminal alkynes have the triple bond at the end of the carbon chain so that a hydrogen atom

More information

Experiment #7 Qualitative Analysis of Anions

Experiment #7 Qualitative Analysis of Anions Experiment #7 Qualitative Analysis of Anions Objective Part I: Identify the presence of each of the following anions: SO 4 2-, CO 3 2-, NO 2 -, Cl -, Br -, I -, and NO 3 -, using qualitative analysis.

More information

EXPERIMENT 3 (Organic Chemistry II) Nitration of Aromatic Compounds: Preparation of methyl-m-nitrobenzoate

EXPERIMENT 3 (Organic Chemistry II) Nitration of Aromatic Compounds: Preparation of methyl-m-nitrobenzoate EXPERIMENT 3 (Organic Chemistry II) Nitration of Aromatic Compounds: Preparation of methyl-m-nitrobenzoate Pahlavan/Cherif Purpose a) Study electrophilic aromatic substitution reaction (EAS) b) Study regioselectivity

More information

The hydrogen halides H-Cl, H-Br, and H-I undergo addition to carbon bonds to give alkyl halides.

The hydrogen halides H-Cl, H-Br, and H-I undergo addition to carbon bonds to give alkyl halides. VII. Reactions of Alkenes: Electrophilic Addition The most characteristic reaction of alkenes is an Electrophilic Addition Reaction. + X Y Examples: X X O 3 O + (cat.) O 2 l 2 2 O O B 3 or 9-BBN BR 2 2

More information

Experiment 6 Qualitative Tests for Alcohols, Alcohol Unknown, IR of Unknown

Experiment 6 Qualitative Tests for Alcohols, Alcohol Unknown, IR of Unknown Experiment 6 Qualitative Tests for Alcohols, Alcohol Unknown, I of Unknown In this experiment you are going to do a series of tests in order to determine whether or not an alcohol is a primary (1 ), secondary

More information

14.1 Introduction to Ethers Naming Ethers Structure and Properties of Ethers. Compounds containing ether groups are quite common.

14.1 Introduction to Ethers Naming Ethers Structure and Properties of Ethers. Compounds containing ether groups are quite common. 14.1 Introduction to Ethers An ether group includes an oxygen atom that is bonded to TWO R groups: 14.1 Introduction to Ethers Compounds containing ether groups are quite common. R groups can be alkyl,

More information

Unit 6 Halides and Halogens. Procedure

Unit 6 Halides and Halogens. Procedure Unit 6 Halides and Halogens The halogens are also involved in double replacement reactions as described in Unit 5. The term HALOGEN is used to describe the halogens in their elemental state (Cl2, Br2,

More information

ORGANIC CHEMISTRY 307 LECTURE POSTING VI

ORGANIC CHEMISTRY 307 LECTURE POSTING VI ORGANI HEMISTRY 307 LETURE POSTING VI Haloalkanes and Nucleophilic Substitution In the past five chapters you (we) have reviewed some basic concepts, have studied one reaction type, and have learned to

More information

The Mechanism of a Substitution Reaction

The Mechanism of a Substitution Reaction The Mechanism of a Substitution Reaction Background Organohalogens are mainly laboratory creations. A few compounds of this type have been found in some organisms, especially in the oceans, but for the

More information

Lecture Notes Chem 51B S. King. Chapter 18 Electrophilic Aromatic Substitution

Lecture Notes Chem 51B S. King. Chapter 18 Electrophilic Aromatic Substitution Lecture otes Chem 51B S. King Chapter 18 Electrophilic Aromatic Substitution I. Electrophilic Aromatic Substitution The most characteristic reaction of aromatic compounds is electrophilic aromatic substitution,

More information

1,4-Di-t-butylbenzene via Friedel-Crafts Alkylation

1,4-Di-t-butylbenzene via Friedel-Crafts Alkylation Exp t 61 1,4-Di-t-butylbenzene via Friedel-Crafts Alkylation from K. L. Williamson, Macroscale and Microscale Organic Experiments, 2nd Ed. 1994, Houghton Mifflin, Boston. p435; revised2/28/02 Prelab Exercise:

More information

Synthetic Experiment PreLab Grading Sheet. PreLab For Exp't #: 60. Title: Alkylation of Mesitylene

Synthetic Experiment PreLab Grading Sheet. PreLab For Exp't #: 60. Title: Alkylation of Mesitylene Exp t 60 Alkylation of Mesitylene Procedure adapted from K. L. Williamson, Macroscale and Microscale Organic Experiments, 2nd Ed. 1994, Houghton Mifflin, Boston, Alkylation of Mesitylene by R. Minard,

More information

Chapter 12 Electrophilic and Nucleophilic Aromatic Substitution

Chapter 12 Electrophilic and Nucleophilic Aromatic Substitution Chapter 12 Electrophilic and Nucleophilic Aromatic Substitution CHAPTER 12 Electrophilic and Nucleophilic Aromatic Substitution Aromatic compounds may undergo substitution reactions. Electrophilic aromatic

More information

Syllabus Review: There is no textbook for this class. I will post my notes online as soon as I have semicoherent notes available for posting.

Syllabus Review: There is no textbook for this class. I will post my notes online as soon as I have semicoherent notes available for posting. Class 1 Welcome: Welcome to organic chemistry 521. I had the privilege of teaching some of you last semester, and those people will be happy to know that this class and its grading scheme are going to

More information

Chem 21 Fall Experiment 8

Chem 21 Fall Experiment 8 Chem 21 Fall 2009 Experiment 8 Kinetics of S N 1 Solvolysis Pre-lab preparation (1) Textbook Ch 8 covers the S N 2 and S N 1 mechanisms. Read/review as necessary. (2) Write balanced rxns (a) for S N 1

More information

Writing a Correct Mechanism

Writing a Correct Mechanism Chapter 2 1) Balancing Equations Writing a Correct Mechanism 2) Using Arrows to show Electron Movement 3) Mechanisms in Acidic and Basic Media 4) Electron rich Species: Nucleophile or Base? 5) Trimolecular

More information

COPYRIGHT FOUNTAINHEAD PRESS

COPYRIGHT FOUNTAINHEAD PRESS Reaction Kinetics: the Iodine Clock Reaction Objective: To investigate the factors that affect the rate of reactions, including concentrations of reactants and temperature; to use kinetics data to derive

More information

Reactions of Grignard Reagents

Reactions of Grignard Reagents Magnesium The Song For alkyl halides' majesty Magnesium is meant, Assisted by completely dry E-ther-e-al sol-vent. Magnesium, Magnesium, A Grignard has M-g, It's understood, its bonds are good From C to

More information

Synthesis of Para Red, part 1

Synthesis of Para Red, part 1 Synthesis of Para Red, part 1 In this lab, you prepare p-nitroaniline by the nitration of acetanilide and subsequent hydrolysis of the nitration product. You will then diazotize this compound and use the

More information

Chem 343 Spring 2007

Chem 343 Spring 2007 hem 343 pring 2007 Problem et 2 Key 1. Indicate the relationship between the two structures. (a) 3 3 o enantiomers o diastereomers o conformers o same o structural isomers (b) 3 3 meso 3 3 o enantiomers

More information

CH421 Experiment 2. Nitration of Aniline: a three-step protecting group strategy to prepare p-nitroaniline

CH421 Experiment 2. Nitration of Aniline: a three-step protecting group strategy to prepare p-nitroaniline CH421 Experiment 2 Nitration of Aniline: a three-step protecting group strategy to prepare p-nitroaniline Reading: Organic Chemistry by John McMurry, 8e, Chapter 16.1-16.5 Techniques: recrystallization,

More information

Chapter 18 Ethers and Epoxides; Thiols and Sulfides

Chapter 18 Ethers and Epoxides; Thiols and Sulfides John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 18 Ethers and Epoxides; Thiols and Sulfides Ethers and Their Relatives An ether has two organic groups (alkyl, aryl, or vinyl) bonded to the same

More information

The alcohol functional group is -O-H and its reactions involve cleavage of the O-H bond or the C-O bond

The alcohol functional group is -O-H and its reactions involve cleavage of the O-H bond or the C-O bond Alcohols: Reactions The alcohol functional group is -- and its reactions involve cleavage of the - bond or the - bond or In either case, there can be a subsequent substitution, or an elimination to form

More information