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Exam 1 February 28, Wednesday (12:05 –12:50) Chapter 1–4 Problem sets/Practice exams will be available at http://www.chem.wisc.edu/courses/343/lee/ Acid / Base in Nonaqueous Solution Leveling Effect: No stronger base than OH- can exist in water. Acid / Base in Nonaqueous Solution Leveling Effect: No stronger base than OH- can exist in water. Acid / Base in Nonaqueous Solution Acid / Base in Nonaqueous Solution Acid / Base in Nonaqueous Solution Leveling Effect: No stronger base than OH- can exist in water. Synthesis of Tritium-labeled Compound Chapter 4 Important Concepts and Principles Ch 4.1–4.7: Branched/unbranched alkanes, Constitutional isomers, Cycloalkanes, IUPAC system Ch 4.8–4.11: Conformation (σ-bond rotation, staggered, eclipsed, gauche, anti), Conformational analysis, Newman projection Torsional strain, Steric hindrance Ring strain (torsional/angle strain), Hyperconjugation Ch 4.12–4.15: Conformation of cyclohexane (chair/boat, equatorial/axial) Ring flip (upper/lower bond), Cis/trans isomers Ch 4.16–4.19: Hydrogenation, Reduction of alkyl halide, Alkylation Alkynide anion, Nucleophile/electrophile Retrosynthetic analysis Chapter 4 Suggested Problems Ch 4.1–4.7: Branched/unbranched alkanes, Constitutional isomers, Cycloalkanes, IUPAC system, Homologs Problem 4.1–4.9, 4.19, 4.21, 4.22, 4.24a, 4.30 Ch 4.8–4.11: Conformation (σ-bond rotation, staggered, eclipsed, gauche, anti), Conformational analysis, Newman projection Torsional strain, Steric hindrance Ring strain (torsional/angle strain), Hyperconjugation Problem 4.10, 4.31, 4.35, 4.41 Ch 4.12–4.15: Conformation of cyclohexane (chair/boat, equatorial/axial) Ring flip (upper/lower bond), Cis/trans isomers Problem 4.11–4.13, 4.39, 4.40, 4.42–4.44, 4.49 Ch 4.16–4.19: Hydrogenation, Reduction of alkyl halide, Alkylation Alkynide anion, Nucleophile/electrophile Retrosynthetic analysis Problem 4.16–4.18, 4.25, 4.27, 4.45 Alkanes/Cycloalkanes Saturated Hydrocarbons Unsaturated Alkane (CnH2n+2) Cycloalkane (CnH2n) Alkene (CnH2n) Alkyne (CnH2n-2) Aromatic Sources of Alkanes: Petroleum (refining / cracking) Shape of Alkanes • What is the shape of these molecules? < Structure > • What these molecules do/how they do? < Function/Mechanism > < Synthesis > • How they can be obtained? Structure of compounds: Composition + Connectivity + Shape Saturated Hydrocarbons Unsaturated Alkane (CnH2n+2) Cycloalkane (CnH2n) Unbranched Branched Shape of Alkanes Structure of compounds: Composition + Connectivity + Shape Saturated Hydrocarbons Alkane (CnH2n+2) Cycloalkane (CnH2n) Unsaturated Different Connectivity: Constitutional Isomers Unbranched Branched Shape of Alkanes Structure of compounds: Composition + Connectivity + Shape Saturated Hydrocarbons Alkane (CnH2n+2) Cycloalkane (CnH2n) Unbranched Branched Unsaturated Different Connectivity: Constitutional Isomers For C167H336, # of constitutional isomers > # of particles observed in the universe Naming Organic Compounds Each different compound should have an unambiguous name (IUPAC system) Saturated Hydrocarbons Unsaturated Alkane (CnH2n+2) Cycloalkane (CnH2n) Unbranched Branched Naming Branched Alkyl Groups Each different compound should have an unambiguous name (IUPAC system) Saturated Hydrocarbons Unsaturated five-carbon group Alkane (CnH2n+2) Cycloalkane (CnH2n) Unbranched Branched Naming Alkyl Halides Each different compound should have an unambiguous name (IUPAC system) IUPAC names Common names Naming Alcohols Each different compound should have an unambiguous name (IUPAC system) IUPAC names Naming Alcohols Each different compound should have an unambiguous name (IUPAC system) Common names
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