ELMHURST CHM 103 - Week 6 Aldehydes and Ketones
School name Elmhurst College
Course Chm 103-
Pages 8

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Week # 6: Aldehydes and KetonesLectures - 15, 16, 17Concepts:Carbonyl group - pi bondBoiling points, polarity, solubilityChiral Molecules (definition), mirror images, Fischer projection,D amd L glyceraldehyde, biological and drug examples.Enantiomer, diasteroisomerHemiacetal and acetal as functional groups, ring hemiacetalsReaction Summary: Write the word equations.(first four are review)Oxidation of primary alcohol:Oxidation of secondary alcohol:Oxidation of tertiary alcohol:Oxidation of aldehyde:Reduction or hydrogenation of aldehyde or ketone:Synthesis of Hemiacetal:Synthesis of Acetal:Ques.1. Summarize the definitions of the three classes of alcohols including an example of each, using 4 carbons. Definition Example Primary: Secondary: Tertiary:Ques. 2. a. Rank the compounds by boiling point (lowest to highest) and by polarity. First write out the structures.propanone, propanol, propane, methyl ethyl ether, and propanalb. Are aldehyde and ketones able to hydrogen bond? What explains their relative high polarity compared to alkanes or ethers?Ques. 3. Which compound is more soluble in water? Explain your reason.a. butanone or butaneb. 3-hexanone or propanonec. 1-butanol or butanalQues. 4.a. Which of the following compounds contains at least one chiral carbons. Circle that carbon.b. Write the structures of D and L glyceraldehyde.Ques. 5. Explain why both mirror images of a compound are not effective as drugs? Use the L-dopa and D-dopa as examples. Draw out the structures centered on the chiral carbons to show the mirror images.CH3CCH2H3COHHCCH2H2CH3COCH3CHCH2H3COHHCCHH2CH3COCH3CH3CNH2CH2HOHO OHOHReview - Subtraction Reactions - Dehydration and OxidationReaction Name Word Equation Example8. Oxidation - pri. alcohol Pri. Alcohol + (O)  aldehyde + water1-propanol + (O) propanal9. Oxidation - sec. alcohol Sec. Alcohol + (O)  ketone + water2-propanol + (O) 2-propanone10. Oxidation - aldehyde Aldehyde + (O)  Acid Propanal + (O) propanoic acid Ques. 6. Write the structures and names of the reactants and products.a) CH3CH2OH + (O) ----->b) CH3CH2CH2OH + (O) ----->c) + (O) -----> d) + (O) ----->Ques. 7: Write the names of the structures below.CH3CHCH2H3COHHCCH2H2CH3COQues. 8: Write the names of the reactant structures:a.b.c.Addition Reactions6. Reduction (H2) Aldehyde or ketone + hydrogen  alcoholPropanal + hydrogenPropanone + hydrogenCH2CHCH3OHH3C+ (O)CHCHCH3OH3C+ (O)+ (O)CH3CHCHH3COHCH3Ques. 9. Write the structures and names of the reactants and products.Ques. 10: Write the name of the reactants and the structures of the products.a.b.CH3CCH2H3COHCCH2H2CH3COHCCHH2CH3COCH3a.b.c.+ H2+ H2+ H2CH3CH3COCH3+ H2+ H2CHH2CCHH3COCH3c.d. Hemiacetal and acetal Functional Groups In the simplest form, the hemiacetal is really the combination of twofunctional groups. A hemiacetal is an alcohol and ether ATTACHED TO THESAME CARBON. An acetal is two ether groups ATTACHED TO THE SAME CARBON.Hemiacetal Formation:The aldehyde and alcohol approach each other as follows because of theattraction of opposite charges on the polar groups. The reaction is written as an equilibrium because the hemiacetal is unstable and reverts back to the original aldehyde and alcohol.1. The alcohol oxygen becomes bonded to the carbonyl carbon to form the ether. 2. The carbon double bond oxygen electrons are used to bond the alcohol hydrogen to the carbonyl oxygen 3. The alcohol oxygen-hydrogen bond is broken The whole process can be remembered by saying: The aldehyde or ketoneoxygen becomes an alcohol. The alcohol oxygen becomes an ether.+ H2CCHH2CH2CCH2CH3O+ H2OQues. 11: Identify the structures below as hemiacetals or acetals:14. Hemiactal Synthesis Alcohol + aldehyde or ketone  hemiacetalEthanal + methanol15. Acetal Synthesis (ether synthesis)Alcohol + hemiactal  acetal + waterHemiacetal (above) +methanolQues. 12: a. If butanone reacts with one molecule of methanol, what is the structure formed?b. If butanone reacts with two molecules of methanol, what is the structure formed?Ques. 13. Write the structures and names of the reactants and products.CHH2CH3COCHH2CH3COH3COHH3COH++


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ELMHURST CHM 103 - Week 6 Aldehydes and Ketones

Course: Chm 103-
Pages: 8
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