Hydrocarbons

ALKANES:

1. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?

2. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?

3. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?

4. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?

5. Draw the structural and condensed formula of the following hydrocarbon. What is the chemical formula?

6. Draw the linear and structural formula of the following hydrocarbon. What is the chemical formula?

CH3  CH2  O  CH2  CH3

7. Draw the linear and structural formula of the following hydrocarbon. What is the chemical formula?

O

CH3  O  C  CH2  CH3
8. Draw the linear and structural formula of the following hydrocarbon. What is the chemical formula?

9. Draw the linear and structural formula of the following hydrocarbon. What is the chemical formula?

CH3

CH3  CH  CH2  CH3

10. Fill in the names/molecular formula, number of carbons and the structures for the first ten alkanes.
Name and Molecular Number of Structure
Formula Carbons

Name Draw
11. Name and draw the substituents that will be used in this class:

Draw
 Name

12. Name the following hydrocarbons:

 CH2  CH3 

CH3  CH2  CH2  CH  CH3

 

 

 
 

13. Draw expanded structural formula for an alkane with three carbon atoms.

14. What is the IUPAC name of this compound?

CH3  CH2  CH2  CH2  CH3

15. What is the IUPAC name of CH3  CH2  CH2  CH3?

16. The skeletal formula shown is that of ________.

17. What is the IUPAC name of the nine-carbon continuous-chain alkane?

18. What is the IUPAC name for the following compound?

CH3  CH2  CH2  CH2  CH2  CH2  CH2  CH2  CH3

19. Using the IUPAC nomenclature system, name the following molecule.

20. Draw the proper structure for cyclopentane.

21. Spell out the full name of the compound.

22. Spell out the full name of the compound.

H3C  CH3

23. Spell out the full name of the compound.

24. Spell out the full name of the compound.

25. Spell out the full name of the compound.

CH3  CH2  CH2  CH3

26. Spell out the full name of the compound.

27. Spell out the full name of the compound.

28. Spell out the full name of the compound.

29. Write the condensed structural formula and draw the expanded structural formula for each of the following.

 Propane

 Hexane

 Heptane

 Cyclopentane

30. What is the IUPAC name for a seven-carbon continuous-chain alkane?

31. What is the name for a six-carbon continuous-chain alkane?

32. According to the IUPAC convention for chemical naming, which part of a hydrocarbon is selected as the main chain for a
hydrocarbon chain?

33. What is the IUPAC name of the following compound?

34. What is the IUPAC name of the following compound?

CH 3

CH3  CH  CH2  CH2  CH2  CH3

35. What is the IUPAC name of the alkyl group CH3  CH2  CH2?

36. What is the IUPAC name of the following compound?

CH3

CH3  CH  CH2  CH2  CH3

37. Alkanes with a branch coming off the straight chain are identified as substituted alkanes. What would be the name of a
straight chain made of 8 carbons with – CH3 groups on the second and fifth carbons?

38. What is the structure for 3-methylpentane?

39. Isomers are molecules that share the same formula and have ________.

40. Indicate whether each of the following pairs represent structural isomers or the same molecule:

and

and


and

41. Draw the condensed structural formula for each of the following alkanes
 3,3-dimethylpentane
  2,3,5-trimethylhexane
 3-ethyl-2-methylheptane

 3-ethyl-2,5-dimethyloctane
 4-ethyl-2,2-dimethyloctane

 1-bromo-2-chloroethane
 3-ethylpentane  2-bromopropane

42. Identify the compounds in each of the following pairs as structural isomers or not structural isomers.


and


and


and


and

43. What is the name of a 4-membered carbon ring with a 2-carbon chain branching off the first carbon?

44. Name the haloalkane that has 7 carbons in a chain, a chlorine on the second carbon, and a bromine on the third carbon.
45. What is the structure of isobutane, also known as 2-methylpropane?

46. Draw the condensed structural formula for each of the following cycloalkanes

 cyclopropane  1,1-dimethylcyclohexane

 cyclobutane  1,3-dimethylcyclohexane

 cyclopentane  1,1,2,4-tetraiodocyclopentane

CONFORMATIONS:

1. Draw two different conformations for 1,2 dichloroethane

2. Draw the different conformations of pentane

3. Draw the conformations for ethane

4. Draw the conformations for hexane

5. Draw the conformations for heptane

ISOMERS

1.

 Describe at least two specific things that these three structures have in common.

 Would these structures be identified as conformers or isomers?

2. Draw and name the different constitutional isomers for a structure with the molecular formula C 5H12 using the condensed
structure and skeletal structure.

3. Draw and name all of the constitutional isomers for C6H14 in the condensed formula and line formula.

4. Draw and name all of the constitutional isomers for C3H6Br2 in the condensed formula and line formula.
5. Draw and name all of the constitutional isomers for C4H9Cl in the condensed formula and line formula.

6. Draw and name all of the constitutional isomers for C7H16 in the condensed formula and line formula.

7. There are two different molecules with the formula C2H6O.

a. Draw the Lewis Structure for each isomer.
b. Identify the molecular geometry around each central atom.
c. Draw the molecule using the skeletal structure.
d. Draw a 3D-sketch for each molecule using the line-dash-wedge system.
e. Indicate whether each molecule is polar or non-polar.
f. Identify the dominant intermolecular force.

Lewis Structure of Molecule 3D drawing (line-dash-wedge)

Isomer #1
C2H6O VE 

Molecular geometry at each central atom(s):

Polar or non-polar?

Line formula:
Dominant intermolecular force:

Isomer #1
C2H6O VE 
 Molecular geometry at each central atom(s):

Polar or non-polar?

Line formula:
Dominant intermolecular force:

8. What is the structure of isobutane, also known as 2-methylpropane?

9. Draw and name all of the constitutional isomers for hexane in the condensed formula and line formula.

10. Draw and name all of the constitutional isomers for C4H8F2 in the condensed formula and line formula.
CIS-TRANS ISOMERS (GEOMETRIC ISOMERS)

1. Can 2-methyl-2-butene form cis-trans isomers? Draw the condensed and line formula for the structure(s).

2. Can the following structure from cis-trans isomerism? If so, show how.

3. For each molecule:

a. Determine whether the molecule can form cis-trans isomers.
b. Draw each structure using the condensed structure and line structure.
c. For each molecule that has cis-trans isomers, draw both the cis- and trans-isomersusing the condensed and line structure.

 1-butene
Can 1-butene form cis-trans isomers?

Condensed structure Skeletal Structure

 2-methyl-2-pentene
Can 2-methyl-2-pentene form cis-trans isomers?

Condensed structure Skeletal Structure

 2-butene
Can 2-butene form cis-trans isomers?

Condensed structure Skeletal Structure

 2,3-dichloro-2-butene
Can 2,3 dichloro-2-butene form cis-trans isomers?

Condensed structure Skeletal Structure

4. State and name whether the following molecules are cis, trans, or neither.

 

 

 




 

 

5. Draw the structure of trans-2-pentene, showing the correct arrangement of atoms around the double bond.
6. Draw the structure of cis-3-heptene, showing the correct arrangement of atoms around the double bond.

7. Draw condensed structural formulas for the following molecules

 cis-2-octene  trans-4-decene

 trans-3-hexene  cis-2-pentene

FUNCTIONAL GROUPS

Name of functional group Properties (drawn)

Alcohol

Carboxylic acid

Ester

Alkene

Phenol

Thiol

Disulfide
 Aldehyde

Ketone

Carbonyl

Carboxylate ion

Amine

Ester

Ammonium ion

Amide

Identify the functional group


 











 













HYDRATION (OF AN ALKENE)

Write the product(s) of the following hydration reactions and state whether they are symmetric or asymmetric alkenes.


H+ catalyst
+¿ H2O


H+ catalyst
+¿ H2O


H+ catalyst
+¿ H2O
 

H+ catalyst
+¿ H2O


H+ catalyst
+¿ H2O


+¿ H2O H+ catalyst

 H+ catalyst
+¿ H2O

CHIRALITY AND ENANTIOMERS

1. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

2. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

3. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
4. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

5. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

6. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

7. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

8. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

9. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.
10. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

11. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

12. Identify the following molecule as chiral or achiral. If it is chiral, locate and label the chiral carbon(s). If it is not chiral,
explain why.

13. Draw the enantiomer for the following molecule.

14. Draw the enantiomer for the following molecule.

15. Draw the enantiomer for the following molecule.

16. Draw the enantiomer for the following molecule.

17. Draw the enantiomer for the following molecule.

18. Draw the enantiomer for the following molecule.

19. Draw the enantiomer for the following molecule.

20. Draw the enantiomer for the following molecule.

21. Draw the enantiomer for the following molecule.

 22. Draw the enantiomer for the following molecule.

23. Draw the enantiomer for the following molecule.

24. Draw the enantiomer for the following molecule.

DEHYDRATION OF AN ALCOHOL

Write the product(s) of the following dehydration reactions.


H+ catalyst

Heat

 H+ catalyst
Heat


H+ catalyst
Heat


H+ catalyst
 Heat

 H+ catalyst
Heat


H+ catalyst
Heat

 H+ catalyst
Heat

H+ catalyst
Heat

 H+ catalyst
Heat

H+ catalyst
Heat

H+ catalyst

Heat

H+ catalyst

Heat

 H+ catalyst
 Heat

H+ catalyst
Heat

H+ catalyst
Heat


H+ catalyst
Heat

 H+ catalyst
Heat


H+ catalyst
Heat