ORGANIC CHEMICAL PATHWAYS Area of Study 2

ORGANIC CHEMICAL PATHWAYS – 1. ORGANIC CHEMISTRY Area of Study 2

Organic Chemistry Naming Compounds 3-chloro-2-methylpropan-1-ol [substituents] | [main part of molecule] [3-chloro-2-methyl] | [propan-1-ol]

Organic Chemistry Naming Compounds 3-chloro-2-methylpropan-1-ol [sub.] [sub.]… | [#C] [C=C?] [principal functional group] [3-chloro] [-2-methyl] | [prop] [an] [-1-ol] Must know functional groups first!!

Organic Chemistry Naming Compounds – Functional Groups methyl (-CH 3 ) ethyl (-CH 2 CH 3 ) chloro (-Cl), bromo (-Br), iodo (-I) amino (-NH 2 ) hydroxyl (-OH) carboxyl (-COOH) amide (-CONH 2 ) ester (-COOR)

Organic Chemistry Naming Compounds 1.Longest carbon chain – if possible with: – principal functional group (COOH, OH or NH 2 ) – if not, with a C=C double bond – determines [#C] 7 hept 5 pent

Organic Chemistry Naming Compounds 2.Identify principal functional group. Number if possible. Determines [principal functional group] – 1) COOH (carboxyl) => -oic acid – 2) OH (hydroxyl) => -ol – 3) NH 2 (amino) => -amine OH on carbon 2 hept -2-ol none pent

Organic Chemistry Naming Compounds 3.Any C=C bonds? Number if possible. Determines [C=C?]. – if C=C => -en(e) (at position) – if no C=C => -an(e) C=C on carbon 5 hept-5-en-2-ol none pentane

Organic Chemistry Naming Compounds 4.Any substituents? Number if possible. Determines [substituents]. – alpha order! chloro (Cl) on carbon 3 3-chlorohept-5-en-2-ol chloro carbon 2, methyl carbon 3 2-chloro-3-methylpentane

Organic Chemistry Naming Esters methyl ethanoate

Organic Chemistry Reactions of Common Functional Groups Alkanes (C n H 2n+2 ) combustion eg. CH 4 (g) + 2 O 2 (g)  CO 2 (g) + 2 H 2 O (g or l) substitution

Organic Chemistry Reactions of Common Functional Groups Chloroalkanes substitution

Organic Chemistry Reactions of Common Functional Groups Alkenes (C n H 2n ) combustion eg. C 2 H 4 (g) + 3 O 2 (g)  2 CO 2 (g) + 2 H 2 O (g or l) addition…

Organic Chemistry Reactions of Common Functional Groups Alkenes (C n H 2n ) - addition

Organic Chemistry Reactions of Common Functional Groups Alkenes (C n H 2n ) - addition

Organic Chemistry Reactions of Common Functional Groups Alkenes (C n H 2n ) - addition

Organic Chemistry Reactions of Common Functional Groups Alkenes (C n H 2n ) - addition

Organic Chemistry Reactions of Common Functional Groups Alkanols (besides combustion) CH 3 CH 2 OH  CH 3 COOH Cr 2 O 7 2- H+H+ NB: PRIMARY ALKANOLS ONLY!

Organic Chemistry Reactions of Common Functional Groups Carboxylic acids combustion acid-base reactions esterification

Organic Chemistry Polymerisation Addition Polymerisation

Organic Chemistry Polymerisation Condensation Polymerisation

Organic Chemistry Determine a set of steps you could undergo to produce ethyl ethanoate from only ethene and inorganic reagents.

ORGANIC CHEMICAL PATHWAYS – 2. ORGANIC ANALYSIS (IR, NMR, AND MS) Area of Study 2

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy BONDS (eg. C=O) have VIBRATION STATES. Different bonds absorb IR light of different wavelengths. IDENTIFY BONDS

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy Formula: C 3 H 6 O acetone (propanone)

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy Formula: C 6 H 14 hexane

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy Formula: C 2 H 4 O 2 ethanoic acid

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy Formula: C 2 H 6 Oethanol

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy Formula: C 5 H 13 N pentan-1-amine

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy Formula: C 5 H 10 pent-1-ene

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy Formula: C 4 H 6 O 2 Double bond equivalents = 2 Clue: it contains only functional groups we have covered, and a CH 3 group bonded to a C atom.

Organic Analysis (IR, NMR, MS) Infra-Red Spectroscopy Formula: C 4 H 6 O 2 vinyl acetate

Organic Analysis (IR, NMR, MS) Nuclear Magnetic Resonance Spectroscopy

Analysing 1 H NMR Spectra: No. peaks = no. chemical environments Integration trace Location of Peaks (next few slides) Splitting

Organic Analysis (IR, NMR, MS) Nuclear Magnetic Resonance Spectroscopy

Formula: C 3 H 6 O 2 ethyl methanoate

Organic Analysis (IR, NMR, MS) Nuclear Magnetic Resonance Spectroscopy Formula: C 3 H 6 O 2 propanoic acid

Organic Analysis (IR, NMR, MS) Nuclear Magnetic Resonance Spectroscopy Formula: C 9 H 12 Clue: it ‘smells good’ (cryptic) area = 5 area = 1 area 6

Organic Analysis (IR, NMR, MS) Nuclear Magnetic Resonance Spectroscopy area = 5 area = 1 area 6 Analysing 13 C NMR Spectra: No. peaks = no. chemical environments NO integration trace NO splitting Location of peaks (shortcut): C-C (0-50 ppm) C-O ( ppm) C=C ( ppm) C=O (150+ ppm)

Organic Analysis (IR, NMR, MS) Mass Spectrometry

area = 5 area = 1 area 6

ORGANIC CHEMICAL PATHWAYS – 3. BIOCHEMISTRY Area of Study 2

Biochemistry Carbohydrates

Biochemistry Lipids

Biochemistry Proteins

Biochemistry Proteins – Amino Acids

Biochemistry Proteins – Polypeptides

Biochemistry Proteins – Levels of Structure Primary Secondary Tertiary (Quaternary)

Biochemistry Proteins – Enzymes

Biochemistry DNA Nucleotide (monomer) -

Biochemistry DNA

Biochemistry Biochemical Fuels Bioethanol Biodiesel Biogas C 6 H 12 O 6 (aq)  2 CH 3 CH 2 OH (aq)+ 2 CO 2 (g)

Biochemistry Medicinal Applications (Aspirin)

Any Questions?