1.1.

5 Non-cyclic Alkanes with up to 7 carbon atoms for C nH2n+2

1. (a)  the molecular formula of methane, two full structural graphic formula representations
are

o (b) and (c) which gives a 3-dimensional (3D) structural formula

impression of the molecule.
o The H-C-H bond angle is 109o. NOTE: all the C-C-H, H-C-H or H-C-H angles are
approximately 109o in all the non-cyclic alkanes shown below.

2. (a)  or (b) or (c) or (d) ethane,

o molecular formula (e) , the skeletal formula is (f) , yes! just a dash!
o NOTE: from (a) to (d) you go from the most abbreviated structural formula representation
to the maximum 3D structural graphic formula representation on a 2D format!

3. (a)  or (b) or (c) or (d)

o (a) and (b) are the abbreviated structural formula for propane,
o (c)/(d) full displayed-graphic structural formula, but (d) is a 3D version to indicate the
spatial arrangement of the atoms,

o for molecular formula (e) and the skeletal formula is (f)

4. (a)  or (b) are abbreviated structural

formula for butane
 o  (normal or n-butane), molecular formula (c) and the skeletal formula is (d)

5. (a)  or (b) are the abbreviated structural formula for

methylpropane (isobutane), the prefix 2- isn't strictly needed. BUT can be added for clarity,
especially for beginners,

o the molecular formula is (c) and

o the skeletal formula is (d) and is the simplest branched hydrocarbon.

6. (a)  or (b) are abbreviated

structural formula

o  for pentane (normal or n-pentane), molecular formula (c) and the skeletal

formula is (d)

7. (a)  (b) abbreviated structural formula for

methylbutane (isopentane),
o (prefix 2- isn't strictly needed, but 2-methybutane helps at the beginning of studying

organic nomenclature), the molecular formula is (c) and the skeletal formula is

(d)

 
8. (a)  or (b) are the abbreviated structural formula for
dimethylpropane (neopentane),
o (the prefix 2,2- isn't strictly needed but can help initially),

o molecular formula (c) and the skeletal formula is (d)

9. (a) or (b)
o are abbreviated structural formula for hexane (normal or n-hexane),

o molecular formula (c) and the skeletal formula is (d)

10. (a)  or (b) are abbreviated

structural formula for
o  2-methylpentane (NOTE: prefix numbers needed from now on),

o molecular formula and the skeletal formula is (d)

11. (a)  or (b)  are

abbreviated structural formula

o  for 3-methylpentane, the molecular formula is (c) and the skeletal formula is

(d)

12. (a)  or (b) are abbreviated structural formula

for
o  2,2-dimethylbutane (NOTE: numbers needed here, cross-check with 7.),
 o molecular formula (c) and the skeletal formula is (d)

13. (a)  or (b) are abbreviated structural

formula for

o 2,3-dimethylbutane, molecular formula (c) and the skeletal formula is (d)

14. (a)  or (b)

o are the abbreviated structural formula for heptane, molecular formula (c)

o and the skeletal formula is (d)

15. (a)  or (b)  

o are the abbreviated structural formula for 2-methylhexane,

o molecular formula (c) and the skeletal formula is (d)

16. (a) or (b)

o are abbreviated structural formula for 3-methylhexane, molecular formula (c)

o and the skeletal formula is (d)

 
17. (a)  or (b) are abbreviated structural
formula

o for 3-ethylpentane, molecular formula (c) and the skeletal formula is (d)

18. (a)  or (b)  are abbreviated

structural formula

o for 2,2-dimethylpentane, molecular formula (c) and the skeletal formula is (d)

19. (a)  or (b)   are

abbreviated structural formula

o for 2,3-dimethylpentane, molecular formula (c) and the skeletal formula is (d)

20. (a)  or (b)   are

abbreviated structural formula

o for 2,4-dimethylpentane, molecular formula (c) and the skeletal formula is (d)

 
21. (a)  or (b)   are
abbreviated structural formula

o  for 3,3-dimethylpentane, molecular formula (c) and the skeletal formula is (d)

22. (a) or (b) are the abbreviated structural

formula for

o 2,2,3-trimethylbutane, molecular formula and the skeletal formula is (d)

1.1.6 Cycloalkanes (general formula  CnH2n & isomeric with non-cyclic alkenes)

 Cycloalkanes are named according to the rules previously described, but the name is based on
the number of carbon atoms in the ring itself.
 The 'smallest' cycloalkanes must have at least 3 carbon atoms in the ring.
 The structures are shown as abbreviated structural formulae and skeletal formulae.
 They are sometimes referred to as examples of alicyclic hydrocarbons, that is, aliphatic in
nature, but with a ring i.e. cyclic-aliphatic compounds, as opposed to an aromatic ring compound
based on a benzene ring.

1. cyclopropane , , note C-C-C bond angle is 60o

2. methylcyclopropane , ,

 
3. 1,1-dimethylcyclopropane , ,

4. 1,2-dimethylcyclopropane , ,

5. ethylcyclopropane , ,

6. cyclobutane , , note C-C-C bond angle is 90o

7. methylcyclobutane , ,

8. 1,1-dimethylcyclobutane , ,

9. 1,2-dimethylcyclobutane , ,

10. 1,3-dimethylcyclobutane , ,

11. ethylcyclobutane , ,
  

12. cyclopentane , ,

13. methylcyclopentane , ,

14. 1,1-dimethylcyclopentane , ,

15. 1,2-dimethylcyclopentane , ,

16. 1,3-dimethylcyclopentane , ,

17. ethylcyclopentane , ,

 
18. propylcyclopentane , ,

19. butylcyclopentane , ,

20. pentylcyclopentane , ,

21. cyclohexane , ,

22. methylcyclohexane , ,

23. 1,1-dimethylcyclohexane , ,

 
24. 1,2-dimethylcyclohexane , ,

25. 1,3-dimethylcyclohexane , ,

26. 1,4-dimethylcyclohexane , ,

27. ethylcyclohexane , ,

28. propylcyclohexane , ,

29. butylcyclohexane , ,

 
 30. pentylcyclohexane , ,

1.1.7 Larger Alkanes with 8-10 carbon atoms CnH2n+2 continued

Illustrated as brief guide to working out the 18 isomers of non-cycloalkanes C 8H18 !!!!!

1. octane , CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3
o Start with the linear (unbranched) carbon chain, then make the next longest chain with a
single, but shortest, carbon branch (-CH3), to give three methylheptanes ...
2. 2-methylheptane, (CH3)2CHCH2CH2CH2CH2CH3

3. 3-methylheptane, CH3CH2CH(CH3)CH2CH2CH2CH3

4. 4-methylheptane, CH3CH2CH2CH(CH3)CH2CH2CH3
o then do double methyl branching permutations to make 6 dimethylhexanes ...

5. 2,2-dimethylhexane, ,

6. 2,3-dimethylhexane, ,

7. 2,4-dimethylhexane, ,
  

8. 2,5-dimethylhexane, ,

9. 3,3-dimethylhexane, ,

10. 3,4-dimethylhexane, ,
o then you can make one ethylhexane ...

11. 3-ethylhexane, ,
o and don't try 2-ethylhexane, because its actually 3-methylheptane using the
nomenclature rules correctly.
o Now you can do a double branching again to make two ethylmethylpentanes ...

12. 3-ethyl-2-methylpentane, ,

13. 3-ethyl-3-methylpentane, ,
o and you can do a triple branching to give four trimethylpentanes ...

14. 2,2,3-trimethylpentane, (CH3)3CCH(CH3)CH2CH3

 15. 2,2,4-trimethylpentane (isooctane), (CH3)3CCH2CH(CH3)2

16. 2,3,3-trimethylpentane, (CH3)2CHC(CH3)2CH2CH3

17. 2,3,4-trimethylpentane, (CH3)2CHCH(CH3)CH(CH3)2

o Then finally, the most branched isomer is the single tetramethylbutane (shortest possible
main chain) ...

18. 2,2,4,4-tetramethylbutane, (CH3)3CC(CH3)3

1.1.8 Examples of isomers of C9H20

 3-ethyl-2,2-dimethylpentane, ,

 3-ethyl-2,3-dimethylpentane, ,

 3-ethyl-2,4-dimethylpentane, ,

 
 3-ethyl-2-methylhexane , ,

 3-ethyl-3-methylhexane , ,

 3-ethyl-4-methylhexane , ,

 4-ethyl-2-methylhexane , ,