Organic Chemistry Module 2 Study Review: Key Concepts and Nomenclature, Exams of Chemistry

A concise review of key concepts in organic chemistry, focusing on nomenclature, properties, and reactions of alkanes, cycloalkanes, alkenes, alkynes, and aromatic compounds. It covers topics such as iupac naming conventions, conformers, angle strain, torsional strain, stereoisomerism, and qualitative reactions for identifying alkenes. The review also includes definitions of important terms like carbocyclic, heterocyclic, functional group, and electrophilic aromatic substitution. It is a useful resource for students studying organic chemistry.

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2025/2026

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Chem 219 Module 2 Study Review
1.
list
prefixes
for
first
10
carbons
in
order:
meth, eth, prop, but, pent, hex, hept, oct, non, dec
2.
hydrocarbon:
compounds composed of only carbon and hydrogen
3.
parent
chain:
longest continuous chain of carbon atoms
4.
substituent:
heteroatom or group of atoms that are attached to the parent chain
5. numerical prefixes for # of identical substituent groups (2-10 in order):
di, tri,
tetra, penta, hexa, hepta, octa, nona, deca
6.
alkane (with
formula):
hydrocarbon containing only single bonds between carbons, CnH2n+2
7.
rules
for
naming
alkanes:
1. longest continues chain is parent chain
2.
number
parent
chain
starting
with
the
end
closest
to
the
first
branch
3.
name using IUPAC rules for substituents
8. IUPAC systematic name order for alkanes:
locant-
(prefix)SubstituentParent
9. in numbering parent chains, if there are two equally long chains...:
select the chain
with the most branches coming ott
10. in numbering parent chains, if the first branch point if the same distance
from either end of the parent
chain...: choose the numbering that gives the lower numbers to the
most substituents
11. in numbering parent chains, if there are only 2 substituents and both are
equidistant from opposite ends of
the parens chain...: choose the numbering direction so
the substituent with the higher alphabetical priority gets the lower locant number
12.
solubility
and
density
properties
of
alkanes:
NOT soluble in water, low density (< 1g/ml) so
floats on top of water
13.
melting and boiling points properties of alkanes: LOW MPs and BPs due to weak attractive
forces between molecules
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Chem 219 Module 2 Study Review

1. list prefixes for first 10 carbons in order: meth, eth, prop, but, pent, hex, hept, oct, non, dec

2. hydrocarbon: compounds composed of only carbon and hydrogen

3. parent chain: longest continuous chain of carbon atoms

4. substituent: heteroatom or group of atoms that are attached to the parent chain

5. numerical prefixes for # of identical substituent groups (2-10 in order): di, tri, tetra, penta, hexa, hepta, octa, nona, deca

6. alkane (with formula): hydrocarbon containing only single bonds between carbons, CnH2n+

7. rules for naming alkanes: 1. longest continues chain is parent chain

2. number parent chain starting with the end closest to the first branch

3. name using IUPAC rules for substituents

8. IUPAC systematic name order for alkanes: locant-(prefix)SubstituentParent

9. in numbering parent chains, if there are two equally long chains...: select the chain with the most branches coming ott

10. in numbering parent chains, if the first branch point if the same distance from either end of the parent

chain...: choose the numbering that gives the lower numbers to the most substituents

11. in numbering parent chains, if there are only 2 substituents and both are equidistant from opposite ends of

the parens chain...: choose the numbering direction so the substituent with the higher alphabetical priority gets the lower locant number

12. solubility and density properties of alkanes: NOT soluble in water, low density (< 1g/ml) so floats on top of water

13. melting and boiling points properties of alkanes: LOW MPs and BPs due to weak attractive forces between molecules

2 /

14. how does branching affect MPs and BPs: branching lowers surface area of the molecule, which in turn lowers VDWFs and thus

lowering BPs and MPs

15. conformers: ditterent shapes of molecules derived from rotations of single bonds

16. staggered conformation: H atoms do not overlap in line of sight (more stable)

17. eclipsed conformation: heteroatoms overlap with one another (less stable)

18. rotamers: conformers that can be swapped with a simple rotation of the C-C bond

19. what conformation do molecules prefer?: molecules adapt conformations that minimize repulsion, so likely staggered (zigzag

formation)

20. cycloalkane: alkane whose carbon skeleton is in a ring

21. how to name cycloalkanes: add prefix "cyclo" to the parent chain portion of the name

22. when naming cycloalkanes, if ONE substituent is present...: NO locant numbers are added and the substituent name is

added in front of the parent name (methylcyclobutane)

23. when naming cycloalkanes, if more than one substituent is present...: carbons on the parent ring are numbered, starting

with the carbon with the substituent group with the highest alphabetical priority and continuing in the direction that gives the other substituents the lowest locant numbers (1- ethyl-2-methyl- cyclohexane)

24. angle strain: occurs when the actual bond angle in the ring is not what VESPR predicts for the atom's electron

geometry angle

25. what is the most stable number of carbons in a chain? Why?: 6, because C6 has bond angles that almost match the VESPR

prediction of a tetrahedral bond angle

4 / the (+) electrophile removes an H resulting in the E attached to the ring and an A-H leftover

42. aliphatic hydrocarbons: alkanes, alkenes, alkynes

43. aromatic hydrocarbons: -arenes, such as benzenes lack of reactivity

very stable

44. conjugation: double bond separated by 1 sigma bond

45. polycyclic aromatic hydrocarbons: more than one benzene ring fused together with each ring sharing 2 or more of the same C atoms

46. in naming monosubstituted benzenes: name of substituent group is added to parent name "benzene"

(clorobenzene)

47. when 2 substituents are present on a benzene: use prefixes to describe location of substituents in relation to one another

(o-dichlorobenzene)

48. prefixes for locating 2 substituents on a benzne: (o) ortho = 1 carbon away

(m) meta = 2 carbon away (p) para = 3 carbon away place letter instead of locant number

49. when 3 or more substituents are present on a benzene: the locant numbers are used to describe the position (1,2,4-

trimethylbenzene)

50. benzene: C6H6 ring with alternating double bonds

51. what reaction is used to pinpoint specific location of double bond? How?: - ozonolysis, O3 acts like scissors and breaks the

double bond apart creating two carbonyl compounds attached to the 2 parts of the molecule

52. how is bromine used in alkene/alkyne reactions: if the orange/brown color of the bromine disappears when added to a compound

5 / the molecule is an alkene/alkyne

53. typical reaction type for alkenes and alkynes: addition reaction where atoms or groups of atoms are added to each carbon in the

multiple bond, causing the bond to become single or double

54. two major classes of hydrocarbons: aliphatic (alkane, alkene, alkyne) and aromatic (benzene)

55. how does surface area impact MPs and BPs: greater surface area means more VDWFs which leads to higher MPs and BPs

56. how to determine if cis/trans isomerism is possible around a double bond: if the substituent comes ott on the same side

it is cis, if on the other side it is trans, if the sides look ditterent it is not possible

57. what are the two qualitative reactions for the presence of an alkene: Bromine

addition (if color disappears it IS an alkene) AND oxidation with KMnO4 (if purple color disappears and leaves brown precipitate it IS an alkene)

58. why do aromatic rings undergo substitution and NOT addition?: the loop of

conjugation (pi-sigma-pi) causes great stability, substitution occurs rather than addition because addition would break the stability of the ring

59. list IUPAC steps for naming alkenes/alkynes: 1. select parent chain that contains both carbons

in multiple bond

2. number locants so the multiple bond has the lower numbers (if equidistant number with 1 closer to 1st branch)

3. indicate multiple bond using lower locant number (2-hexene NOT 3-hexene)

60. in naming alkenes/alkynes if more than one pi bond is present...: number the patent chain from the end nearest to the

first pi bond

61. is a double C bond and triple C bond are present AND equidistant from the ends number locants...: so that

the double bond gets the lower numbers

62. how to name cyclic alkenes/alkynes without substituents: no locant numbers needed (cyclohexane)

63. how to number cyclic alkenes/alkynes with substituents: number so the multiple bond contains number 1-2 and the substituents