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An overview of organic compounds, focusing on hydrocarbons and their derivatives, including alkanes, alkenes, alkynes, aromatics, and their representations through chemical formulas, structural formulas, and line structures. It also covers isomers, functional groups, and common organic compound names.
Typology: Exercises
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just C and H C, H, N, O, X, etc Hydrocarbons : just C and H atoms
alkane: C-C alkene: C=C (^) alkyne: C≡C
H C
H
H
C
H
H
H sp (^3) sp^2
C C
H
H
H
H sp
H C C H (^) aromatic: sp^2
C C C
C
C C
H
H
H H
H
H
Alkanes are saturated : all C atoms are sp^3 , with four bonds to four atoms, CnH2n+ All other hydrocarbons are unsaturated : multiple bonds or rings, fewer than 2n+2 H atoms
Representing Organic Compounds
chemical formula CH 4 C 2 H 6 C 3 H 8 C 4 H 8 C 6 H 6 condensed structural formula
structural formula (Lewis)
H C
H
H
H H C
H
H
C
H
H
H H C
H
H
C
H C H
H H H
H C
H
H
C
H C H
C H
H
H
C C C
C
C C
H
H
H H
H
H
line structure –––
Line structure: each C-C bond is a line, H atoms on C are omitted – always four bonds to C!
same molecule (^) different molecules
Note: groups can rotate about a C-C single bond (σ only), but not a C=C double (σ + π)!
Isomers : compounds with the same molecular formula, but different structures
carbon backbone (skeletal isomers): (^) CH 3 (CH 2 ) 3 CH 3 pentane
CH 3 CH(CH 3 )CH 2 CH 3 2-methylbutane
C(CH 3 ) 4 2,2-dimethylpropane
functional group position (positional isomers):
OH CH^3 (CH^2 )^2 OH 1-propanol
OH (^) CH 3 CH(OH)CH 3 2-propanol
functional group type (functional isomers):
CH 3 CH 2 OH ethanol
CH 3 OCH 3 dimethylether
B DC A
B A (^) CD
B CD A
not super- imposable!
CH 3 C C H H
CH 3
cis -butene trans -butene
CH 3 C C H CH 3
H
Functional Group Compound Prefix/Suffix Example IUPAC Name (Common Name) R-H alkane -ane CH 3 CH 3 ethane
C C (^) alkene -ene H 2 C=CH 2 ethene (ethylene)
C C (^) alkyne -yne HC≡CH ethyne (acetylene)
R-X haloalkane halo- CH 3 Cl chloromethane
R-OH alcohol -ol (hydroxy-) CH 3 OH methanol
R-NH 2 amine -amine (amino-)
ethylamine aminoethane
R-O-R ether ether (alkoxy-) CH 3 OCH 3 dimethyl ether
C
O
R H
aldehyde -al CH 3 CH
O (^) ethanal (acetaldeyde)
C
O
R R
ketone -one CH 3 CCH 3
O (^) propanone (acetone)
R C
O
O H
carboxylic acid -oic acid (^) CH 3 COH
O (^) ethanoic acid (acetic acid)
R C
O
O R
ester -oate (^) CH 3 COCH 3
O (^) methyl ethanoate (methyl acetate)
R C
O
NH 2
amide -amide CH 3 CNH 2
O (^) ethanamide (acetamide)
R = alkyl group, an unfunctionalized saturated chain; X = halogen
ethylene C^ C
H
H
H
H
formaldehyde (^) HCH
O acetaldehyde (^) CH 3 CH
O
acetylene H^ C^ C H^ formic acid (^) HCOH
O acetic acid (^) CH 3 COH
O
benzene phenol OH^ acetone (^) CH 3 CCH 3
O
toluene aniline NH 2 benzaldehyde (^) CH
O
xylene styrene benzoic acid (^) COH
O