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Organic Compounds: Hydrocarbons, Functional Groups, and Isomers, Exercises of Organic Chemistry

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

2021/2022

Uploaded on 09/12/2022

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Organic Compounds: hydrocarbons and derivatives
just C and H C, H, N, O, X, etc
Hydrocarbons: just C and H atoms
alkane: C-C alkene: C=C alkyne: CC
HC
H
H
C
H
H
H
sp3 sp2
CC
H
H
H
H
sp
CCHH
aromatic:
sp2
C
CC
C
CC
H
H
HH
H
H
Alkanes are saturated: all C atoms are sp3, with four bonds to four atoms, CnH2n+2
All other hydrocarbons are unsaturated: multiple bonds or rings, fewer than 2n+2 H atoms
Representing Organic Compounds
chemical formula CH4 C
2H6 C
3H8 C
4H8 C
6H6
condensed
structural formula CH4 CH3CH3 CH3CH2CH3 CH3CH2CH=CH2
structural formula
(Lewis) HC
H
H
H
HC
H
H
C
H
H
H
HC
H
H
C
H
C
H
H
H
H
HC
H
H
C
H
C
H
C
H
H
H
C
CC
C
CC
H
H
HH
H
H
line structure –––
Line structure: each C-C bond is a line, H atoms
on C are omitted – always four bonds to C!
98
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
Isomers: compounds with the same molecular formula, but different structures
Structural Isomers: isomers that differ in the bonding arrangement and connectivity of
atoms. Such isomers can differ in terms of:
carbon backbone
(skeletal isomers): CH3(CH2)3CH3
pentane
CH3CH(CH3)CH2CH3
2-methylbutane
C(CH3)4
2,2-dimethylpropane
functional group position
(positional isomers): OH CH3(CH2)2OH
1-propanol
OH
CH3CH(OH)CH3
2-propanol
functional group type
(functional isomers):
CH3CH2OH
ethanol
CH3OCH3
dimethylether
B
A
D
C
B
AD
C
B
A
C
D
not
super-
imposable!
Stereoisomers: isomers that have the same connectivity, but differ in the
spatial arrangement of atoms. There are two classes:
Geometric isomers: stereoisomers that differ
in the relative orientation of substituents
e.g. cis- and trans-alkenes
CH3
CC
HH
CH3
cis-butene trans-butene
CH3
CC
HCH
3
H
Enantiomers (or optical isomers):
stereoisomers that are chiral, non-superimposable on a mirror image (Eğe Ch6)
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Organic Compounds : hydrocarbons and derivatives

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

CH 4 CH 3 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH=CH 2

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

Isomers : compounds with the same molecular formula, but different structures

  • Structural Isomers : isomers that differ in the bonding arrangement and connectivity of atoms. Such isomers can differ in terms of:

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!

  • Stereoisomers : isomers that have the same connectivity, but differ in the spatial arrangement of atoms. There are two classes:
    • Geometric isomers: stereoisomers that differ in the relative orientation of substituents e.g. cis- and trans- alkenes

CH 3 C C H H

CH 3

cis -butene trans -butene

CH 3 C C H CH 3

H

  • Enantiomers (or optical isomers): stereoisomers that are chiral, non-superimposable on a mirror image (Eğe Ch6)

Organic Functional Group List

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-)

CH 3 CH 2 NH 2

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

Organic Common Names

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