c. Oxidizing agent shown here oxidizes 2º alcohols to ketones and 1º alcohols to carboxylic acids. 3º alcohols DO NOT REACT.

Size: px
Start display at page:

Download "c. Oxidizing agent shown here oxidizes 2º alcohols to ketones and 1º alcohols to carboxylic acids. 3º alcohols DO NOT REACT."

Transcription

1 Exam 1 (Ch 17 and Review of CEM 331) Answer Key: 1. ne-step Questions: You need to know reagents for reagent arrows and to be able to draw products. I know a lot of them seem to look alike its your job to sort them out. SCl 2 is used to make chlorides from alcohols, PCl 3 is used to dehydrate. C 3 S 2 Cl is mesyl chloride (MsCl), p-c 3 C 6 4 S 2 Cl is tosyl chloride (TsCl). TMSCl is trimethyl silyl chloride, used with triethylamine, NEt 3, and is a protecting group for alcohols, like DP, dihydropyran, used with an acid catalyst, +, also forms a protecting group (TP group). PCC (Cr 3 with pyridinium hydrochloride) is used to oxidize, as are Cr 3, Na 2 Cr 2 7 and KMn 4 while LiAl 4 and NaB 4 are used to reduce. a. C 3 S 2 Cl is MsCl and converts an alcohol into a good leaving group without affecting the stereochemistry of the chiral center. No inversion of the stereochemistry. C 3 S 2 Cl pyridine Ms b. Take home message count your carbons people. You are starting with 8 carbons and ending with 10. Do the math. nly adding 2 carbons. Answer: C 3 C 2 MgBr. c. xidizing agent shown here oxidizes 2º alcohols to ketones and 1º alcohols to carboxylic acids. 3º alcohols D NT REACT. KMn 4, 3 + d. Tertiary alcohol is forming tertiary chloride. Reagent? NT thionyl chloride Use Cl. C 3 Cl C 3 e. Grignard reagents add one time to a ketone (yes that s a ketone not a cyclic ester the ring does NT open) and once to an aldehyde: C 3 MgBr f. Williamson ether synthesis adding three carbons to the alcohol. LEARN IT! 1. Na or K and 2. C 3 C 2 C 2 Br. Please do not write that backwards as C 2 C 2 C 3 Br. Carbon atoms should have four bonds

2 g. I think everyone knows that sodium borohydride only reacts with aldehydes and ketones. Look at the left side closely. That C 3 is NT attached to the carbonyl. That s a ketone on the left, not an ester Reduction of both the ketone and the aldehyde occurs. 3 C NaB 4 3 C 2. [10 pts] Name the following compounds according to IUPAC nomenclature: (from Problem Set online) a. #1 shown below was the problem on the exam. #2 was what most people were trying to name. See the structural difference. The first is a cyclohexanol with three other groups attached. The other is a cyclohexenol with two other groups attached. Numbering of ring #1 starts at alcohol position and you number around the ring so as to arrive at the lowest possible sum (go CCW). The double bond is not IN the ring so you do not give it lower numbers. It s a prefix called methylene and does not have any priority. [#2 would start its numbering at the alcohol and go CW so the double bond has the second priority and as low of a numbering as possible but its not the problem on the exam!] versus C 3 #1 #2 C 3 Answer: 3-methoxy-2-methyl-5-methylenecyclohexanol (automatically assumes is on #!). b. Most common mistakes: Couldn t count to nine (parent) or number from correct side (so ether is on lowest number). Answer: 4-ethoxy-2,7-nonadiene-5-ol. 3. [6 pts] In each of the molecules shown below, circle the two different functional group and identify what type each is (i.e. halide, alcohol, ketone, etc). See Problem Set online. aromatic ring alcohol alkene ester amide epoxide

3 4. [6 pts] For each transformation shown, label as an oxidation, a reduction or neither: [See Problem Set online] a. Adding to BT ends of the double bond - oxidation b. 2 bonds to become 2 bonds to N - neither c. 3 bonds to become 1 bond to and 2 bonds to (not shown) - reduction 5. [28 pts] Synthesis: Most everyone got the idea of synthesis although not knowing reagents or paying attention to structures caused some people some difficulties. a. I Na or K PCC b. Most people could make the Grignard reagent but then got confused when they needed to react it with a carbonyl (on the arrow) to form the alcohol product. You got too used to seeing the carbonyl in front of the arrow. Take off the mental blinders PBr 3 Br Mg MgBr c. Some of you don t like the Cuprate reagent yet which is why many of you got the last reagent wrong get used to it. More people got the Grignard reagent wrong because they

4 didn t recognize that a new CARBN was added, even though they drew is (because everyone knew what PBr 3 does, you were easily able to draw that alcohol). PCC C 3 MgBr this is a C! PBr 3 (C 3 ) 2 CuLi Br d. You were on your own for this problem. You needed to add three carbons to the left side. Everyone seemed to recognize a Grignard was required. That secondary ketone needed to be oxidized first but there s an aldehyde in the way. Reduce the aldehyde on the right end (you have to any way) and protect it FIRST, then deal with the left end. Reagents: 1. NaB 4 or LA 2. Protecting group (either TMSCl with NEt 3 or DP, + ) 3. PCC (so you don t accidentally remove the protecting group, PCC is the best choice), 4. Ethyl magnesium bromide, C 3 C 2 MgBr, and finally removes the protecting group (or F - for the TMS group). 6. [12 pts] Mechanisms take a lot of practice Thus, I suggest you start practicing + 7. [12 pts] Sequence Question: Identify the structures of the Compounds A, B, C and D formed in the following sequence of reactions. Word problems are always tougher if you don t know the NAMES a. 1,4-Pentanediol is reacted with one equivalent of trimethylsilyl chloride and triethylamine to form Compound A. 1 equiv. TMSCl, NEt 3 TMS Compound A

5 Note for future problems a backwards TMS group is NT an SMT group b. Compound A is oxidized using PCC and then reacted with methyl magnesium bromide, C 3 MgBr, to form Compound B. TMS Compound A 1. PCC 2. C 3 MgBr TMS Compound B c. The addition of fluoride anion to Compound B results in the formation of Compound C, which then can easily react with thionyl chloride and pyridine to form Compound D, C 6 13 Cl. TMS Compound B F - Compound C d. Compound D will react with Na or K to form the following cyclic ether in a Williamson ether synthesis reaction: Compound C SCl 2 pyridine Cl Compound D And Compound D does an intramolecular Williamson Ether Synthesis: Na Compound D 8. [8 pts] Thought Provoking Questions (a.k.a. Short Answers): Choose 2 of the 3 following questions. If you answer more than two, indicate which two you wish to be graded otherwise the first two will be chosen for you. a. Explain why a primary alcohol, like 1-pentanol shown below, cannot be converted into a primary chloride, using the reagent Cl. Cl The conversion of an alcohol to a chloride using Cl occurs via an SN1 type mechanism that requires the formation of a carbocation intermediate. The primary alcohol here cannot form a stable carbocation therefore it won t be able to react to form a chloride. Cl

6 b. In the following transformation, should the alcohol be converted into a halide or a tosylate to achieve the desired product? Explain your answer. 1.? 2. NaC 3 C 3 The second step of the reaction involves a salt that means you have a strong nucleophile which will react SN2 fashion. That will cause one inversion to happen in the sequence in step two. verall, you want one inversion to occur, therefore you don t want to do an inversion in the first step. Forming a halide does an inversion. Forming a tosylate does not cause an inversion. Form a tosylate in the first step! c. Explain why increasing the number of alkyl groups surrounding an alcohol decreases the acidity of the alcohol proton. The more alkyl groups, the more sterically hindered, the less able an alkoxide anion (anion of an alcohol) can be SLVATED to stabilize the anion.

Chapter 10 Outline: Alcohols

Chapter 10 Outline: Alcohols Chapter 10 Outline: Alcohols Review Nomenclature, Structure & Physical Properties on your own 1. Acidity of Alcohols 2. Reactions of Alcohols 3. Reactions of Thiols You should do all the problems in the

More information

CHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models

CHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models CEM 203 Final Exam December 15, 2010 Your name: ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This test contains 15 pages Time: 2h 30 min 1. / 16 2. / 15 3. / 24

More information

But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens).

But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens). Reactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations the majority of which are either oxidation or reduction type reactions. Normally: Oxidation

More information

FIRST EXAMINATION. Name: CHM 332

FIRST EXAMINATION. Name: CHM 332 ame: CM 332 FIRST EXAMIATI All answers should be written on the exam in the spaces provided. Clearly indicate your answers in the spaces provided; if I have to guess as to what or where your answer is,

More information

(Neither an oxidation or reduction: Addition or loss of H +, H 2 O, HX).

(Neither an oxidation or reduction: Addition or loss of H +, H 2 O, HX). eactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations the majority of which are either oxidation or reduction type reactions. xidation is a

More information

Química Orgânica I. Ciências Farmacêuticas Bioquímica Química AFB QO I 2007/08 1

Química Orgânica I. Ciências Farmacêuticas Bioquímica Química AFB QO I 2007/08 1 Química rgânica I Ciências Farmacêuticas Bioquímica Química AFB Q I 2007/08 1 alcohols Adaptado de rganic Chemistry, 6th Edition; Wade rganic Chemistry, 6 th Edition; McMurry AFB Q I 2007/08 2 Typical

More information

Loudon Chapter 10 Review: Alcohols & Thiols Jacquie Richardson, CU Boulder Last updated 4/26/2016

Loudon Chapter 10 Review: Alcohols & Thiols Jacquie Richardson, CU Boulder Last updated 4/26/2016 Alcohols (R) and thiols (RS) have many reactions in common with alkyl halides, but they don t do everything exactly the same. The main difference between this and alkyl halide chemistry is that unlike

More information

Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides

Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides Learning objectives: 1. Provide both IUPAC and common (when applicable) names for alcohols and ethers. 2. Describe the physical properties

More information

Lecture Notes Chem 51C S. King. Chapter 20 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation & Reduction

Lecture Notes Chem 51C S. King. Chapter 20 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation & Reduction Lecture Notes Chem 51C S. King Chapter 20 Introduction to Carbonyl Chemistry; rganometallic Reagents; xidation & Reduction I. The Reactivity of Carbonyl Compounds The carbonyl group is an extremely important

More information

For example, 2-ethyloctan-3-ol which can also be called. 2-ethyl-3-octanol.

For example, 2-ethyloctan-3-ol which can also be called. 2-ethyl-3-octanol. Alcohols & Ethers Worksheet Part A Name: The focus of this chapter can be thought of as the organic version of water. When H 2 has one or both of its hydrogens replaced by an R group we get alcohols and

More information

DAMIETTA UNIVERSITY. Energy Diagram of One-Step Exothermic Reaction

DAMIETTA UNIVERSITY. Energy Diagram of One-Step Exothermic Reaction DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 5 Dr Ali El-Agamey 1 Energy Diagram of One-Step Exothermic Reaction The vertical axis in this graph represents the potential energy. The transition

More information

CHEM 203. Final Exam December 18, This a closed-notes, closed-book exam. You may use your set of molecular models

CHEM 203. Final Exam December 18, This a closed-notes, closed-book exam. You may use your set of molecular models CEM 203 Final Exam December 18, 2013 Your name: This a closed-notes, closed-book exam You may use your set of molecular models This test consists of 10 pages Time: 2h 30 min 1. / 20 2. / 20 3. / 30 4.

More information

Chemistry 35 Exam 2 Answers - April 9, 2007

Chemistry 35 Exam 2 Answers - April 9, 2007 Chemistry 35 Exam 2 Answers - April 9, 2007 Problem 1. (14 points) Provide the products for the reactions shown below. If stereochemistry is important, be sure to indicate stereochemistry clearly. If no

More information

CHEM 203. Final Exam December 12, This a closed-notes, closed-book exam. You may use your set of molecular models. This test contains 11 pages

CHEM 203. Final Exam December 12, This a closed-notes, closed-book exam. You may use your set of molecular models. This test contains 11 pages CEM 203 Final Exam December 12, 2012 Your name: This a closed-notes, closed-book exam You may use your set of molecular models This test contains 11 pages Time: 2h 30 min 1. / 20 2. / 24 3. / 26 4. / 30

More information

Oxidation of alcohols Chromic Acid KMnO4 PCC Swern 1 ROH RCOOH RCOOH RCHO RCHO 2 ROH Ketone Ketone Ketone Ketone 3 ROH NR NR NR NR

Oxidation of alcohols Chromic Acid KMnO4 PCC Swern 1 ROH RCOOH RCOOH RCHO RCHO 2 ROH Ketone Ketone Ketone Ketone 3 ROH NR NR NR NR Chapter 11 xidation in rganic terms xidation Reduction Neither Addition of, X2; loss of 2 Addition of 2; loss of or X2 Anytime you oxidize one carbon but reduce another (ex. Adding and to adjacent carbons)

More information

CHEM 203. Final Exam December 16, This a closed-notes, closed-book exam. You may use your set of molecular models

CHEM 203. Final Exam December 16, This a closed-notes, closed-book exam. You may use your set of molecular models CEM 203 Final Exam December 16, 2014 Your name: This a closed-notes, closed-book exam You may use your set of molecular models This test consists of 10 pages Time: 2h 30 min 1. / 20 2. / 20 3. / 30 4.

More information

ORGANIC - CLUTCH CH ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION

ORGANIC - CLUTCH CH ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION !! www.clutchprep.com CONCEPT: ALDEHYDE NOMENCLATURE Replace the suffix of the alkane -e with the suffix On the parent chain, the carbonyl is always terminal, and receive a location As substituents, they

More information

ALCOHOLS AND PHENOLS

ALCOHOLS AND PHENOLS ALCOHOLS AND PHENOLS ALCOHOLS AND PHENOLS Alcohols contain an OH group connected to a a saturated C (sp3) They are important solvents and synthesis intermediates Phenols contain an OH group connected to

More information

Chapter 12: Carbonyl Compounds II

Chapter 12: Carbonyl Compounds II Chapter 12: Carbonyl Compounds II Learning bjectives: 1. Recognize and assign names to aldehydes and ketones. 2. Write the mechanism for nucleophilic addition and nucleophilic addition-elimination reactions

More information

Chapter 12. Alcohols from Carbonyl Compounds Oxidation-Reduction & Organometallic Compounds. Structure

Chapter 12. Alcohols from Carbonyl Compounds Oxidation-Reduction & Organometallic Compounds. Structure Chapter 12 Alcohols from Carbonyl Compounds xidation-eduction & rganometallic Compounds Created by Professor William Tam & Dr. Phillis Chang Structure ~ 120 o ~ 120 o C ~ 120 o Carbonyl carbon: sp 2 hybridized

More information

Chapter 17: Alcohols and Phenols

Chapter 17: Alcohols and Phenols hapter 17: Alcohols and Phenols sp 3 alcohol phenol (aromatic alcohol) pka~ 16-18 pka~ 10 Alcohols contain an group connected to a saturated carbon (sp 3 ) Phenols contain an group connected to a carbon

More information

Alcohol Synthesis. Dr. Sapna Gupta

Alcohol Synthesis. Dr. Sapna Gupta Alcohol Synthesis Dr. Sapna Gupta Synthesis of Alcohols Alcohols can be synthesized from several functional groups. Nucleophilic substitution of O - on alkyl halide ydration of alkenes water in acid solution

More information

CHEM 203. Final Exam December 18, 2013 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models

CHEM 203. Final Exam December 18, 2013 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models CEM 203 Your name: Final Exam December 18, 2013 ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This test consists of 10 pages Time: 2h 30 min 1. / 20 2. / 20 3.

More information

b.p.=100 C b.p.=65 C b.p.=-25 C µ=1.69 D µ=2.0 D µ=1.3 D

b.p.=100 C b.p.=65 C b.p.=-25 C µ=1.69 D µ=2.0 D µ=1.3 D Alcohols I eading: Wade chapter 10, sections 10-1- 10-12 Study Problems: 10-35, 10-37, 10-38, 10-39, 10-40, 10-42, 10-43 Key Concepts and Skills: Show how to convert alkenes, alkyl halides, and and carbonyl

More information

Alcohols, Ethers, & Epoxides

Alcohols, Ethers, & Epoxides Alcohols, Ethers, & Epoxides Alcohols Structure and Bonding Enols and Phenols Compounds having a hydroxy group on a sp 2 hybridized carbon enols and phenols undergo different reactions than alcohols. Chapter

More information

Learning Guide for Chapter 15 - Alcohols (II)

Learning Guide for Chapter 15 - Alcohols (II) Learning Guide for Chapter 15 - Alcohols (II) I. Introduction to alcohol reactivity II. Reactions of alcohols with acids III. Reactions of alcohols with electrophiles alogenated phosphorus and sulfur compounds

More information

Chapter 13: Alcohols and Phenols

Chapter 13: Alcohols and Phenols Chapter 13: Alcohols and Phenols [ Chapter 9 Sections: 9.10; Chapter 13 Sections: 13.1-13.3, 13.9-13.10] 1. Nomenclature of Alcohols simple alcohols C3 C3C2 Eddie Sachs 1927-1964 larger alcohols find the

More information

Chemistry 234 Practice Exam 3. The Periodic Table

Chemistry 234 Practice Exam 3. The Periodic Table ame: Last First MI Chemistry 234 Practice Exam 3 Instructions: The first 15 questions of this exam should be answered on the provided Scantron. You must use a pencil for filling in the Scantron sheet.

More information

Loudon Chapter 19 Review: Aldehydes and Ketones CHEM 3331, Jacquie Richardson, Fall Page 1

Loudon Chapter 19 Review: Aldehydes and Ketones CHEM 3331, Jacquie Richardson, Fall Page 1 Loudon Chapter 19 eview: Aldehydes and Ketones CEM 3331, Jacquie ichardson, Fall 2010 - Page 1 Beginning with this chapter, we re looking at a very important functional group: the carbonyl. We ve seen

More information

Allyl radicals are especially stable due to resonance ( and double bond switch places):

Allyl radicals are especially stable due to resonance ( and double bond switch places): Ch 10 Alkyl Halides Nomenclature Rules The parent is the longest alkyl chain or ring. The #1 C for a chain is at the end that is nearest to the first substituent. The #1 C for a ring possesses the first

More information

(1) Recall the different types of intermolecular interactions. (2) Look at the structure and determine the correct answer.

(1) Recall the different types of intermolecular interactions. (2) Look at the structure and determine the correct answer. MCAT rganic Chemistry - Problem Drill 11: Carboxylic Acids Question No. 1 of 10 Question 1. What kinds of interactions are holding together the carboxylic acid dimer shown? Question #01 3 C C 3 (A) Van

More information

Alcohols: Contain a hydroxy group( OH) bonded to an sp 2 or sp 3 hybridized

Alcohols: Contain a hydroxy group( OH) bonded to an sp 2 or sp 3 hybridized Lecture Notes hem 51B S. King hapter 9 Alcohols, Ethers, and Epoxides I. Introduction Alcohols, ether, and epoxides are 3 functional groups that contain σ-bonds. Alcohols: ontain a hydroxy group( ) bonded

More information

REALLY, REALLY STRONG BASES. DO NOT FORGET THIS!!!!!

REALLY, REALLY STRONG BASES. DO NOT FORGET THIS!!!!! CHEM 345 Problem Set 4 Key Grignard (RMgX) Problem Set You will be using Grignard reagents throughout this course to make carbon-carbon bonds. To use them effectively, it will require some knowledge from

More information

CHEM 203. Midterm Exam 1 October 31, 2008 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models

CHEM 203. Midterm Exam 1 October 31, 2008 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models CEM 203 Midterm Exam 1 ctober 31, 2008 Your name: ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This exam contains 8 pages Time: 1h 30 min 1. / 15 2. / 16 3. /

More information

ORGANIC - CLUTCH CH ALCOHOLS AND CARBONYL COMPOUNDS.

ORGANIC - CLUTCH CH ALCOHOLS AND CARBONYL COMPOUNDS. !! www.clutchprep.com CONCEPT: INTRO TO REDOX Oxidation reactions involve an increase in the content of a molecule Reduction reactions involve an increase in the content of a molecule EXAMPLE: Label the

More information

Note: You must have your answers written in pen if you want a regrade!!!!

Note: You must have your answers written in pen if you want a regrade!!!! NAME (Print): SIGNATURE: Chemistry 310N Dr. Brent Iverson 2nd Midterm March 27, 2008 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long,

More information

The Organic Acids. Carboxylic Acids * *

The Organic Acids. Carboxylic Acids * * arboxylic Acids The rganic Acids Some Notation: Acids and their conjugate bases pka ~ 15 - weak acid arboxylic Acid pka ~ 4 moderate acid - arboxylate Anion pka ~ -7 very strong acid l - l arboxylic acids

More information

Loudon Chapter 20 & 21 Review: Carboxylic Acids & Derivatives CHEM 3331, Jacquie Richardson, Fall Page 1

Loudon Chapter 20 & 21 Review: Carboxylic Acids & Derivatives CHEM 3331, Jacquie Richardson, Fall Page 1 Loudon Chapter 20 & 21 eview: Carboxylic Acids & Derivatives CEM 3331, Jacquie ichardson, Fall 2010 - Page 1 These two chapters cover compounds which are all at the three bonds to more electronegative

More information

Chemistry Exam 2. The Periodic Table

Chemistry Exam 2. The Periodic Table Name: Last First MI Chemistry 234-002 Exam 2 Spring 2017 Dr. J. sbourn Instructions: The first 18 questions of this exam should be answered on the provided Scantron. You must use a pencil for filling in

More information

Suggested solutions for Chapter 28

Suggested solutions for Chapter 28 s for Chapter 28 28 PBLEM 1 ow would you make these four compounds? Give your disconnections, explain why you chose them and then give reagents for the. 2 2 Me S Exercises in basic one- group C X disconnections.

More information

Physical Properties. Alcohols can be: CH CH 2 OH CH 2 CH 3 C OH CH 3. Secondary alcohol. Primary alcohol. Tertiary alcohol

Physical Properties. Alcohols can be: CH CH 2 OH CH 2 CH 3 C OH CH 3. Secondary alcohol. Primary alcohol. Tertiary alcohol Chapter 10: Structure and Synthesis of Alcohols 100 Physical Properties Alcohols can be: CH 3 CH 3 CH CH 2 OH * Primary alcohol CH 3 OH CH * CH 2 CH 3 Secondary alcohol CH 3 CH 3 * C OH CH 3 Tertiary alcohol

More information

Chem 263 Notes March 2, 2006

Chem 263 Notes March 2, 2006 Chem 263 Notes March 2, 2006 Average for the midterm is 102.5 / 150 (approx. 68%). Preparation of Aldehydes and Ketones There are several methods to prepare aldehydes and ketones. We will only deal with

More information

ORGANIC - BROWN 8E CH ALDEHYDES AND KETONES.

ORGANIC - BROWN 8E CH ALDEHYDES AND KETONES. !! www.clutchprep.com CONCEPT: ALDEHYDE NOMENCLATURE Replace the suffix of the alkane -e with the suffix On the parent chain, the carbonyl is always terminal, and receive a location As substituents, they

More information

CARBONYL COMPOUNDS: OXIDATION-REDUCTION REACTION

CARBONYL COMPOUNDS: OXIDATION-REDUCTION REACTION CARBONYL COMPOUNDS: OXIDATION-REDUCTION REACTION Introduction Several functional groups contain the carbonyl group Carbonyl groups can be converted into alcohols by various reactions Structure of the Carbonyl

More information

Suggested solutions for Chapter 32

Suggested solutions for Chapter 32 s for Chapter 32 32 PBLEM 1 Explain how the stereo- and regio- chemistry of these reactions are controlled. Why is the epoxidation only moderately diastereoselective, and why does the amine attack where

More information

Learning Guide for Chapter 14 - Alcohols (I)

Learning Guide for Chapter 14 - Alcohols (I) Learning Guide for Chapter 14 - Alcohols (I) I. Introduction to Alcohols and Thiols II. Acid/base Behavior of Alcohols, Phenols, and Thiols III. Nomenclature of Alcohols IV. Synthesis of Alcohols Previous

More information

Lecture 15. More Carbonyl Chemistry. Alcohols React with Aldehydes and Ketones in two steps first O R'OH, H + OR" 2R"OH R + H 2 O OR" 3/8/16

Lecture 15. More Carbonyl Chemistry. Alcohols React with Aldehydes and Ketones in two steps first O R'OH, H + OR 2ROH R + H 2 O OR 3/8/16 Lecture 15 More Carbonyl Chemistry R" R C + R' 2R" R C R" R' + 2 March 8, 2016 Alcohols React with Aldehydes and Ketones in two steps first R', + R R 1 emiacetal reacts further in acid to yield an acetal

More information

Chapter 11 - Alcohols and Ethers 1

Chapter 11 - Alcohols and Ethers 1 Andrew Rosen Chapter 11 - Alcohols and Ethers 1 11.1 - Structure and Nomenclature - The common naming calls alcohols as alkyl alcohols (eg: methyl alcohol) - The common names of ethers have the groups

More information

Alcohols, Ethers and Epoxides. Chapter Organic Chemistry, 8th Edition John McMurry

Alcohols, Ethers and Epoxides. Chapter Organic Chemistry, 8th Edition John McMurry Alcohols, Ethers and Epoxides Chapter 17-18 Organic Chemistry, 8th Edition John McMurry 1 Introduction Structure and Bonding Alcohols contain a hydroxy group (OH) bonded to an sp 3 hybridized carbon. 2

More information

Chapter 17: Alcohols and Phenols. Based on McMurry s Organic Chemistry, 7 th edition

Chapter 17: Alcohols and Phenols. Based on McMurry s Organic Chemistry, 7 th edition Chapter 17: Alcohols and Phenols Based on McMurry s Organic Chemistry, 7 th edition Alcohols and Phenols Alcohols contain an OH group connected to a a saturated C (sp 3 ) They are important solvents and

More information

Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions. McMurray Text Chapter 21

Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions. McMurray Text Chapter 21 Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution eactions McMurray Text Chapter 21 Carboxylic Acid Derivatives X Acid alide Ester ' Acid Anhydride ' N 2 Amide (1 ) Nomenclature Acid alides

More information

CHEMISTRY Topic #8: Oxidation and Reduction Reactions Fall 2018 Dr. Susan Findlay

CHEMISTRY Topic #8: Oxidation and Reduction Reactions Fall 2018 Dr. Susan Findlay CEMISTRY 2600 Topic #8: xidation and Reduction Reactions Fall 2018 Dr. Susan Findlay xidation States of Carbon Carbon can have any oxidation state from -4 (C 4 ) to +4 (C 2 ). As a general rule, increasing

More information

Ch 17 Alcohols and Phenols

Ch 17 Alcohols and Phenols Ch 17 Alcohols and Phenols Alcohols are compounds with a hydroxyl group (OH) attached to an sp 3 C. Phenols are compounds with a hydroxyl group (OH) attached to an aromatic sp 2 C. Classification of Alcohols

More information

Alcohols. Have seen many reactions to synthesize alcohols: In this chapter we will study reactions of the alcohols

Alcohols. Have seen many reactions to synthesize alcohols: In this chapter we will study reactions of the alcohols Alcohols ave seen many reactions to synthesize alcohols: In this chapter we will study reactions of the alcohols Oxidation Need to understand the nomenclature of organic reduction/oxidation In general

More information

2.222 Practice Problems 2003

2.222 Practice Problems 2003 2.222 Practice Problems 2003 Set #1 1. Provide the missing starting compound(s), reagent/solvent, or product to correctly complete each of the following. Most people in the class have not done this type

More information

Ch.17 Alcohols and Phenols

Ch.17 Alcohols and Phenols Ch.17 Alcohols and Phenols C An alcohol A phenol An enol - Me: wood alcohol: made from wood - industrial preparation of methanol: C + 2 2 400 o C Zinc oxide/chromia C 3 - Ethanol: fermentation of grains

More information

The Final Learning Experience

The Final Learning Experience Chemistry 210 Organic Chemistry I Fall Semester 2000 Dr. Rainer Glaser Examination #5 Reactions of Alcohols and Related Reactions The Final Learning Experience Wednesday, December 20, 2000, 1:00-3:00 Name:

More information

Module9. Nuclear Magnetic Resonance Spectroscopy Nuclear Magnetic Resonance (NMR) spectroscopy - Chemical shift - Integration of signal area

Module9. Nuclear Magnetic Resonance Spectroscopy Nuclear Magnetic Resonance (NMR) spectroscopy - Chemical shift - Integration of signal area 1 CHEMISTRY 263 HOME WORK Lecture Topics: Module7. Hydrogenation of Alkenes The Function of the Catalyst - Syn and anti- addition Hydrogenation of Alkynes - Syn- addition of hydrogen: Synthesis of cis-alkenes

More information

Chapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds

Chapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds Chapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds Introduction Several functional groups contain the carbonyl group Carbonyl groups can be converted into alcohols

More information

UCSC, Binder. CHEM 8B Organic Chemistry II FINAL EXAM, Version A (300 points)

UCSC, Binder. CHEM 8B Organic Chemistry II FINAL EXAM, Version A (300 points) UCSC, Binder TA Name SID CEM 8B rganic Chemistry II FINAL EXAM, Version A (300 points) In each of the following problems, use your knowledge of organic chemistry conventions to answer the questions in

More information

Strategies for Organic Synthesis

Strategies for Organic Synthesis Strategies for rganic Synthesis ne of the things that makes chemistry unique among the sciences is synthesis. Chemists make things. New pharmaceuticals, food additives, materials, agricultural chemicals,

More information

Reactions at α-position

Reactions at α-position Reactions at α-position In preceding chapters on carbonyl chemistry, a common reaction mechanism observed was a nucleophile reacting at the electrophilic carbonyl carbon site NUC NUC Another reaction that

More information

Chapter 9 Aldehydes and Ketones Excluded Sections:

Chapter 9 Aldehydes and Ketones Excluded Sections: Chapter 9 Aldehydes and Ketones Excluded Sections: 9.14-9.19 Aldehydes and ketones are found in many fragrant odors of many fruits, fine perfumes, hormones etc. some examples are listed below. Aldehydes

More information

Organic Chemistry 1 CHM 2210 Exam 4 (December 10, 2001)

Organic Chemistry 1 CHM 2210 Exam 4 (December 10, 2001) Exam 4 (December 10, 2001) Name (print): Signature: Student ID Number: There are 12 multiple choice problems (4 points each) on this exam. Record the answers to the multiple choice questions on THIS PAGE.

More information

Chapter 7: Alcohols, Phenols and Thiols

Chapter 7: Alcohols, Phenols and Thiols Chapter 7: Alcohols, Phenols and Thiols 45 -Alcohols have the general formula R-OH and are characterized by the presence of a hydroxyl group, -OH. -Phenols have a hydroxyl group attached directly to an

More information

First 2-Hour Exam. By printing your name below, you pledge that

First 2-Hour Exam. By printing your name below, you pledge that Chem 3331 Fall 2004 Exam # 1 1 Name First 2-our Exam By printing your name below, you pledge that "n my honor, as a University of Colorado at Boulder student, I have neither given nor received unauthorized

More information

When H and OH add to the alkyne, an enol is formed, which rearranges to form a carbonyl (C=O) group:

When H and OH add to the alkyne, an enol is formed, which rearranges to form a carbonyl (C=O) group: Next Up: Addition of, : The next two reactions are the Markovnikov and non-markovnikov additions of and to an alkyne But you will not see alcohols form in this reaction! When and add to the alkyne, an

More information

Summary of Alcohol Syntheses, Ch. 10 (and Review of Old Ones).

Summary of Alcohol Syntheses, Ch. 10 (and Review of Old Ones). Chem 350 Jasperse Ch. 10 Notes 1 Summary of Alcohol Syntheses, Ch. 10 (and eview of ld nes). 1 Na Na Potassium (K) analogous. Key way to convert alcohol to alkoxide, reactive as S N 2 nucleophile and E2

More information

You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded.

You must have your answers written in PERMANENT ink if you want a regrade!!!! This means no test written in pencil or ERASABLE INK will be regraded. NAME (Print): SIGNATURE: Chemistry 320N Dr. Brent Iverson 1st Midterm Feb. 13, 2014 Please print the first three letters of your last name in the three boxes Please Note: This test may be a bit long, but

More information

Chemistry 2030 Introduction to Organic Chemistry Fall Semester 2017 Dr. Rainer Glaser

Chemistry 2030 Introduction to Organic Chemistry Fall Semester 2017 Dr. Rainer Glaser Chemistry 2030 Introduction to Organic Chemistry Fall Semester 2017 Dr. Rainer Glaser Examination #3 Nucleophilic Substitutions & Eliminations, Alcohols, and Ethers Thursday, November 2, 2017, 8:25-9:15

More information

Chapter 20 Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution

Chapter 20 Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution ucleophilic Acyl Substitution hapter 20 arboxylic Acid Derivatives ucleophilic Acyl Substitution Y (1) need to have Y as a u Y u u + Y (2) could not happen with aldehydes or ketones as : and : are poor

More information

Synthesis of Nitriles a. dehydration of 1 amides using POCl 3 : b. SN2 reaction of cyanide ion on halides:

Synthesis of Nitriles a. dehydration of 1 amides using POCl 3 : b. SN2 reaction of cyanide ion on halides: I. Nitriles Nitriles consist of the CN functional group, and are linear with sp hybridization on C and N. Nitriles are non-basic at nitrogen, since the lone pair exists in an sp orbital (50% s character

More information

Introduction & Definitions Catalytic Hydrogenations Dissolving Metal Reduction Reduction by Addition of H- and H+ Oxidation of Alcohols Oxidation of

Introduction & Definitions Catalytic Hydrogenations Dissolving Metal Reduction Reduction by Addition of H- and H+ Oxidation of Alcohols Oxidation of CEM 241- UNIT 4 xidation/reduction Reactions Redox chemistry 1 utline Introduction & Definitions Catalytic ydrogenations Dissolving Metal Reduction Reduction by Addition of - and + xidation of Alcohols

More information

ALCOHOLS: Properties & Preparation

ALCOHOLS: Properties & Preparation ALLS: Properties & Preparation General formula: -, where is alkyl or substitued alkyl. Ar-: phenol - different properties. Nomenclature 1. ommon names: Name of alkyl group, followed by word alcohol. 2.

More information

Chapter 11 Reactions of Alcohols. Types of Alcohol Reactions

Chapter 11 Reactions of Alcohols. Types of Alcohol Reactions hapter 11 Reactions of Alcohols Types of Alcohol Reactions Dehydration to alkene (Discussed in hap 7) xidation to aldehyde, ketone Substitution to form alkyl halide Reduction to alkane Esterification Tosylation

More information

Lecture 18. Oxidation and Reduction. Oxidation. Reduction O CH 4 CH 3 OH H C H. Chemistry 328N

Lecture 18. Oxidation and Reduction. Oxidation. Reduction O CH 4 CH 3 OH H C H. Chemistry 328N Lecture 18 xidation and Reduction C 4 C 3 C C C xidation Reduction March 27, 2018 Suppose you want to make this compound????? C + BrC 2 C 2 C?? CC 2 C 2 C 4-ydroxy-4-phenylbutanal It s an alcohol. Use

More information

Topic 9. Aldehydes & Ketones

Topic 9. Aldehydes & Ketones Chemistry 2213a Fall 2012 Western University Topic 9. Aldehydes & Ketones A. Structure and Nomenclature The carbonyl group is present in aldehydes and ketones and is the most important group in bio-organic

More information

Chem 263 Nov 7, elimination reaction. There are many reagents that can be used for this reaction. Only three are given in this course:

Chem 263 Nov 7, elimination reaction. There are many reagents that can be used for this reaction. Only three are given in this course: hem 263 Nov 7, 2013 Preparation of Ketones and Aldehydes from Alcohols xidation of Alcohols [] must have at least 1 E elimination reaction [] = oxidation; removal of electrons [] = reduction; addition

More information

acetaldehyde (ethanal)

acetaldehyde (ethanal) hem 263 Nov 2, 2010 Preparation of Ketones and Aldehydes from Alkenes zonolysis 1. 3 2. Zn acetone 1. 3 2. Zn acetone acetaldehyde (ethanal) Mechanism: 3 3 3 + - oncerted reaction 3 3 3 + ozonide (explosive)

More information

Chem 263 Nov 3, 2016

Chem 263 Nov 3, 2016 hem 263 Nov 3, 2016 Preparation of Aldehydes from Acid alides? + l l acid chloride aka acyl chloride aldehyde Needed: 2 Actual eagents: 2 /Pd Al This is lithium tri-t-butoxy aluminum hydride, a very sterically

More information

Once familiar with chiral centers, models, drawings and mental images NOW: Final representation of chiral centers: Fischer Projections

Once familiar with chiral centers, models, drawings and mental images NOW: Final representation of chiral centers: Fischer Projections Once familiar with chiral centers, models, drawings and mental images NOW: Final representation of chiral centers: Fischer Projections Fischer Projections are 2-dimensional representations of 3-dimensional

More information

Topic 6 Alkyl halide and carbonyl compounds Organic compounds containing a halogen

Topic 6 Alkyl halide and carbonyl compounds Organic compounds containing a halogen Topic 6 Alkyl halide and carbonyl compounds rganic compounds containing a halogen ompounds are named in standard way, eg: 3 1 3 3 2 3 2-iodo-2-methylpropane (tertiary alkyl halide) l 3 4-chlorotoluene

More information

Chapter 1 Reactions of Organic Compounds. Reactions Involving Hydrocarbons

Chapter 1 Reactions of Organic Compounds. Reactions Involving Hydrocarbons Chapter 1 Reactions of Organic Compounds Reactions Involving Hydrocarbons Reactions of Alkanes Single bonds (C-C) are strong and very hard to break, therefore these compounds are relatively unreactive

More information

Organic Chemistry Semester II 1st unit specialty reactions (mechanisms not emphasized)

Organic Chemistry Semester II 1st unit specialty reactions (mechanisms not emphasized) rganic Chemistry Semester II 1st unit specialty reactions (mechanisms not emphasized) 1. X addition to an alkyne powerful method to add halogens (Cl,, I) to an alkyne to create geminal dihalides (pages

More information

Ethers can be symmetrical or not:

Ethers can be symmetrical or not: Chapter 14: Ethers, Epoxides, and Sulfides 175 Physical Properties Ethers can be symmetrical or not: linear or cyclic. Ethers are inert and make excellent solvents for organic reactions. Epoxides are very

More information

CHM 292 Final Exam Answer Key

CHM 292 Final Exam Answer Key CHM 292 Final Exam Answer Key 1. Predict the product(s) of the following reactions (5 points each; 35 points total). May 7, 2013 Acid catalyzed elimination to form the most highly substituted alkene possible

More information

What is in Common for the Following Reactions, and How Do They Work?

What is in Common for the Following Reactions, and How Do They Work? What is in Common for the Following Reactions, and ow Do They Work? You should eventually be able to draw the mechanism for these (and other) reactions 13 Key Intermediate 1 Br-Br Na Br 2 C 3 -I Me NaMe

More information

Reactions of Chapter 10 Worksheet and Key

Reactions of Chapter 10 Worksheet and Key 1) Alcohol Fermentation Reactions of Chapter 10 Worksheet and Key Alcohol fermentation is a series of chemical reaction that convert sugar molecules, such a glucose, into ethanol and C 2. The overall reaction

More information

I pledge my honor that I have neither given nor received aid on this examination

I pledge my honor that I have neither given nor received aid on this examination Chemistry 220b, Section 1 Exam 1 (100 pts) Tuesday, February 3, 2015 Chapters 13, 15, 16 Name Write and sign the VU onor Pledge: I pledge my honor that I have neither given nor received aid on this examination

More information

Score: Homework Problem Set 6 Iverson CH320N Due Friday, March 10. NAME (Print): Chemistry 320N Dr. Brent Iverson 6th Homework March 3, 2017

Score: Homework Problem Set 6 Iverson CH320N Due Friday, March 10. NAME (Print): Chemistry 320N Dr. Brent Iverson 6th Homework March 3, 2017 omework Problem Set 6 Iverson 320 Due Friday, March 10 AME (Print): SIGATURE: hemistry 320 Dr. Brent Iverson 6th omework March 3, 2017 Please print the first three letters of your last name in the three

More information

Chapter 20: Aldehydes and Ketones

Chapter 20: Aldehydes and Ketones Chapter 20: Aldehydes and Ketones [Chapter 20 Sections: 20.1-20.7, 20.9-10.10, 20.13] 1. Nomenclature of Aldehydes and Ketones ' ketone aldehyde f both aldehydes and ketones, the parent chain is the longest

More information

DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE

DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 6 Dr Ali El-Agamey 1 Oxidation States Easy for inorganic salts: CrO 4 2- reduced to Cr 2 O 3. KMnO 4 reduced to MnO 2. Oxidation: Gain of O,

More information

When we deprotonate we generate enolates or enols. Mechanism for deprotonation: Resonance form of the anion:

When we deprotonate we generate enolates or enols. Mechanism for deprotonation: Resonance form of the anion: Lecture 5 Carbonyl Chemistry III September 26, 2013 Ketone substrates form tertiary alcohol products, and aldehyde substrates form secondary alcohol products. The second step (treatment with aqueous acid)

More information

Score: Homework Problem Set 9 Iverson CH320N Due Monday, April 17. NAME (Print): Chemistry 320N Dr. Brent Iverson 9th Homework April 10, 2017

Score: Homework Problem Set 9 Iverson CH320N Due Monday, April 17. NAME (Print): Chemistry 320N Dr. Brent Iverson 9th Homework April 10, 2017 omework Problem Set 9 Iverson C0N Due Monday, April 7 NAME (Print): SIGNATURE: Chemistry 0N Dr. ent Iverson 9th omework April 0, 07 Please print the first three letters of your last name in the three boxes

More information

Topic 6 Alkyl halide and carbonyl compounds Organic compounds containing a halogen

Topic 6 Alkyl halide and carbonyl compounds Organic compounds containing a halogen Topic 6 Alkyl halide and carbonyl compounds rganic compounds containing a halogen ompounds are named in standard way 3 1 3 3 2 3 2-iodo-2-methylpropane (tertiary alkyl halide) l 3 4-chlorotoluene (aryl

More information

Partial Periodic Table

Partial Periodic Table CEM 3311, Fall 2011 Professor Walba Third our Exam November 17, 2011 scores: 1) 20 2) 20 3) 20 4) 20 5) 20 100 CU onor Code Pledge: n my honor, as a University of Colorado at Boulder tudent, I have neither

More information

CHEM 345 Problem Set 07 Key

CHEM 345 Problem Set 07 Key CHEM 345 Problem Set 07 Key 1.) Fill in the appropriate reaction arrow. The starting material is on the left, the product is on the right. Use. Simple Ring Size. 5 and 6 are favored. 3 is not. That s it.

More information

75. A This is a Markovnikov addition reaction. In these reactions, the pielectrons in the alkene act as a nucleophile. The strongest electrophile will

75. A This is a Markovnikov addition reaction. In these reactions, the pielectrons in the alkene act as a nucleophile. The strongest electrophile will 71. B SN2 stands for substitution nucleophilic bimolecular. This means that there is a bimolecular rate-determining step. Therefore, the reaction will follow second-order kinetics based on the collision

More information

Spring Term 2012 Dr. Williams (309 Zurn, ex 2386)

Spring Term 2012 Dr. Williams (309 Zurn, ex 2386) Chemistry 242 Organic Chemistry II Spring Term 2012 Dr. Williams (309 Zurn, ex 2386) Web Page: http://math.mercyhurst.edu/~jwilliams/ jwilliams@mercyhurst.edu (or just visit Department web site and look

More information

CHEM1902/ N-8 November Consider the following reaction sequences beginning with the carboxylic acid, E.

CHEM1902/ N-8 November Consider the following reaction sequences beginning with the carboxylic acid, E. CEM1902/4 2014--8 ovember 2014 Consider the following reaction sequences beginning with the carboxylic acid, E. 6 ame compounds E and G. E: propionic acid G: methyl propionate Propose structures for compounds

More information