1. VII. Organic

2. Organic compounds contain carbon atoms which bond to one another in chains, rings, and networks to form a variety of structures. Organic compounds can be named using the IUPAC system. (3.1ff)
J Deutsch 2003

3. Hydrocarbons are compounds that contain only carbon and hydrogen
Hydrocarbons are compounds that contain only carbon and hydrogen. Saturated hydrocarbons contain only single carbon-carbon bonds. Unsaturated hydrocarbons contain at least one multiple carbon-carbon bond. (3.1gg)
J Deutsch 2003

4. Homologous series of hydrocarbons:
Saturated hydrocarbons
Alkanes
Only single bonds between carbons
Name ends in ___ane
General formula CnH2n+2
Methane CH4 Ethane C2H6
Unsaturated hydrocarbons
Contain at least one double or triple bond
Alkenes
Contain one double bond
Name ends in ___ene
General formula CnH2n
Alkynes
Contain one triple bond
Name ends in ___yne
General formula CnH2n-2
J Deutsch 2003

5. Table Q gives the general formula and examples (name and structure) of the homologous series of hydrocarbons.
J Deutsch 2003

6. Regents Question: 06/03 #24
Which element has atoms that can form single, double, and triple covalent bonds with other atoms of the same element?
hydrogen
(2) oxygen
(3) fluorine
(4) carbon þ
J Deutsch 2003

7. Table P gives the prefix used to name the first 10 hydrocarbons in an homologous series.
J Deutsch 2003

8. The prefix of the name tells you how many carbons in the chain
The prefix of the name tells you how many carbons in the chain.The suffix tells you the type of hydrocarbon.
Number of Carbons
Prefix
Example
Alkane
CnH2n+2
Alkene
CnH2n
Alkyne CnH2n-2 1
Meth
Methane
CH4 2
Eth
Ethane
C2H6
Ethene
C2H4
Ethyne
C2H2 3
Prop
Propane
C3H8
Propene
C3H6
Propyne
C3H4 4
But
Butane
C4H10
Butene
C4H8
Butyne
C4H6 5
Pent
Pentane
C5H12
Pentene
C5H10
Pentyne
C5H8
J Deutsch 2003

9. Alkanes are saturated hydrocarbons.
Regents Question: 06/03 #21
Which hydrocarbon is saturated?
(1) propene
(2) ethyne
(3) butene
(4) heptane þ
Alkanes are saturated hydrocarbons.
J Deutsch 2003

10. A structural formula show the way the atoms are arranged.
Methane Ethane
H H H
H C H H C C H
Each line represents a covalent bond - a shared pair of electrons.
J Deutsch 2003

11. A structural formulas show the way the atoms are arranged.
propene
H H
H C C C H
H H
ethyne
H C C H
The double bonds makes this hydrocarbon an alkene
The triple bonds makes this hydrocarbon an alkyne
J Deutsch 2003

12. Regents Question: 01/03 #13
The empirical formula of a compound is CH2 Which molecular formula is correctly paired with a structural formula for this compound? þ
J Deutsch 2003

13. Chains of carbons can be branched
A carbon group connected to a chain is called an alkyl group.
To name the alkyl group, use the prefix for the number of carbons and add yl.
-CH3 H
H C
Methyl
-C2H5
H H
H C C
Ethyl
J Deutsch 2003

14. Carbon always has 4 bonds.
Hydrogen always has 1 bond
Oxygen always has 2 bonds
Nitrogen always has 3 bonds
C or C or C
H O or O N
J Deutsch 2003

15. Carbon always has four bonds.
Regents Question: 08/02 #42
Which structural formula is incorrect?
Carbon always has four bonds. þ
J Deutsch 2003

16. Naming hydrocarbons with alkyl groups:
Find the longest continuous chain of carbons. This is the backbone. Find the name of the backbone.
Find the name of the alkyl group (or groups) attached to the backbone.
Name the alkyl group and then the name of the backbone.
Use a number to indicate which carbon the alkyl group is attached to if necessary.
J Deutsch 2003

17. Find the name of this hydrocarbon.
H C H
H H H H H
H C C C C C C H
H H H H H H
Find the alkyl group
Find the longest chain 1 6 2 5 3 4 4 3 5 2 6 1 3-
methyl
hexane
Counting from each direction find the carbon where the alkyl group is attached (the lower number)
J Deutsch 2003

18. The longest chain does not have to be drawn straight.
H C H
H H H H
H C C C C C H
H H H H H H
H C H
H H H H
H C C C C C H
H H H H H
3-methylhexane
J Deutsch 2003

19. Chains of carbons can form rings
Use a prefix cyclo when a ring is formed
To make a ring, two Hydrogen atoms are removed
Cyclopentane is a 5 carbon ring with all single bonds.
J Deutsch 2003

20. Organic acids, alcohols, esters, aldehydes, ketones, ethers, halides, amines, amides, and amino acids are categories of organic molecules that differ in their structures. Functional groups impart distinctive physical and chemical properties to organic compounds. (3.1hh)
J Deutsch 2003

21. Reference Table R lists all the functional groups.
J Deutsch 2003

22. Reference Table R Cont’d.
J Deutsch 2003

23. Regents Question: 06/03 #44
Given the formulas of four organic compounds:
Which pair below contains an alcohol and an acid?
(1) a and b (3) b and d
(2) a and c (4) c and d þ
J Deutsch 2003

24. Naming Halocarbons (-X)
Halocarbons (or halides) have a halogen (F, Cl, Br, I) in place of a hydrogen
Name the halogen first (fluoro, chloro, bromo, iodo) then name the alkane
If there are more than 2 carbons in the chain, use a number to indicate which carbon the –X group is attached to. (Number from the direction that gives the smallest number)
1-chloropropane
2-bromobutane
H H Cl
H C C C H
H H H
H Br H H
H C C C C H
H H H H
J Deutsch 2003

25. Naming Alcohols (-OH) Alcohols have the hydroxyl group -OH
The prefix is the number of carbons in the longest chain
Name the alkane and drop the letter e
The suffix is ol
If there are more than 2 carbons in the chain, use a number to indicate which carbon the –OH group is attached to. (Number from the direction that gives the smallest number)
1-propanol
2-propanol
H H OH
H C C C H
H H H
H OH H
H C C C H
H H H
J Deutsch 2003

26. Regents Question: 08/02 #20 þ Which compound is an alcohol? propanal
(2) ethyne
(3) butane
(4) methanol þ
J Deutsch 2003

27. Naming Ethers (-O-) Ethers have an Oxygen in the chain of carbons
Name the alkyl groups on either side of the O that is in the chain
If both alkyl groups are the same it is named once with the prefix DI in front of it.
H H H
H C C O C H
Methyl ethyl ether
H H
H C O C H
Dimethyl ether
J Deutsch 2003

28. Naming Aldehydes (-CHO)
Aldehydes have a double bonded Oxygen on the last carbon in the chain.
Name the alkane, drop the e and add __al
propanal
methanal
H H O
H C C C H
H H O
H C H
J Deutsch 2003

29. Naming Ketones (-CO-)
Ketones have a double bonded Oxygen on a carbon in the middle of the chain. (Not the last carbon)
Name the alkane, drop the e and add __one
If there are more than 4 carbons in the chain, use a number to indicate the location of the =O
butanone
3-pentanone
H H O H
H C C C C H
H H H
H H O H H
H C C C C C H
H H H H
J Deutsch 2003

30. Naming Organic Acids (-COOH)
Acids have a double bonded Oxygen and an –OH on the last carbon in the chain.
Name the acid, drop the e and add __oic acid
This is OH and not HO…the Carbon is bonded to the O
Propanoic acid
Pentanoic acid
H H O
H C C C OH
H H
O H H H H
HO C C C C C H
H H H H
J Deutsch 2003

31. Naming Amines (-NH2)
Amines have a nitrogen bonded to the carbon chain. The nitrogen may have two, one or no hydrogen atoms bonded to it.
Name the alkane, drop the e and add __amine
If there are more than two carbon atoms, use a number to indicate which carbon the N is attached to.
ethanamine
2-Pentanamine
H H
H C C NH2
H NH2 H H H
H C C C C C H
H H H H H
J Deutsch 2003

32. Name the folowing: Ethanoic acid 1-Propanamine Ethanal 2-butene
H H H H
H C C C N H
H H H
H O
H C C OH H
Ethanoic acid
1-Propanamine
H O
H C C H H
H H H H
H C C C C H
H H
Ethanal
2-butene
H H O H H H
H C C C C C C H
H H H H H
H OH H H H
H C C C C C H
H H H H H
3-hexanone
2-pentanol
J Deutsch 2003

33. Regents Question: 06/02 #17
Which compound is classified as a hydrocarbon?
Ethane
(2) Ethanol
(3) chloroethane
(4) ethanoic acid þ
J Deutsch 2003

34. Regents Question: 06/02 #48 þ Which pair of compounds are alcohols?
J Deutsch 2003

35. Regents Question: 01/03 #49
Which type of organic compound is represented
by the structural formula shown below?
(1) aldehyde
(2) alcohol
(3) ether
(4) ester þ
J Deutsch 2003

36. Isomers of organic compounds have the same molecular formula but different structures and properties. (3.1ii)
Pentane C5H12
Methylbutane C5H12
H H H H
H C C C C H
H H H
H C H H
H H H H H
H C C C C C H
J Deutsch 2003

37. Examples of isomers: 1-butanol (C4H9OH) diethyl ether (C2H5OC2H5)
4 Carbon, 10 Hydrogen, 1 Oxygen
propanal (C2H5CHO) propanone (CH3COCH3)
3 Carbon, 6 Hydrogen, 1 Oxygen
Isomers have the same chemical formulas but different structural formulas.
J Deutsch 2003

38. Regents Question: 06/03 #25 þ Which compound is an isomer of pentane?
(1) butane
(2) propane
(3) methyl butane
(4) methyl propane þ
J Deutsch 2003

39. Regents Question: 06/02 #19 þ Which formula is an isomer of butane?
J Deutsch 2003

40. Regents Question: 08/02 #55 Given the structural formula for butane:
Draw the structural formula for an isomer of butane.
H H H
H C C C H
H H
H C H H
J Deutsch 2003

41. Regents Question: 01/03 #18 þ Which compound has an isomer?
J Deutsch 2003

42. In a multiple covalent bond, more than one pair of electrons are shared between two atoms.
Alkenes have one double bond
H H
C C
Alkynes have one triple bond
H C C H
Ethene C2H4
Ethyne C2H2
J Deutsch 2003

43. Alkenes and Alkynes are unsaturated.
Unsaturated organic compounds contain at least one double or triple bond. (5.2e)
Alkenes and Alkynes are unsaturated.
By breaking the multiple bond in alkenes and alkynes, more hydrogen atoms can be added
Alkanes are saturated.
Alkanes do not have multiple bonds, therefore, they already have as many hydrogen atoms as they could possibly hold.
J Deutsch 2003

44. Regents Question: 01/03 #25
In saturated hydrocarbons, carbon atoms are bonded to each other by
(1) single covalent bonds, only
(2) double covalent bonds, only
(3) alternating single and double covalent bonds
(4) alternating double and triple covalent bonds þ
J Deutsch 2003

45. Types of organic reactions include: addition, substitution, polymerization, esterification, fermentation, saponification, and combustion. (3.2c)
J Deutsch 2003

46. Organic Reactions-Addition
H2, Cl2, Br2, HCl, HBr is added to an unsaturated hyrdrocarbon. Both atoms are added to where the double (or triple) bond was located.
Key to look for – Unsaturated hydrocarbon reactant and one product.
H H
C C
H H
C C
Cl Cl
H C C H
H H
+ Cl2
J Deutsch 2003

47. Organic Reactions-Addition Cont’d
Addition of hydrogen H2 Can be used to saturate and unsaturated hydrocarbon. It uses a catalyst such as platinum (Pt)
H H
C C
H H
C C
H H
H C C H
+ H2 Pt
J Deutsch 2003

48. Regents Question: 01/03 #26
Which formula correctly represents the product
of an addition reaction between ethene and chlorine?
CH2Cl2
(2) CH3Cl
(3) C2H4Cl2
(4) C2H3Cl þ
J Deutsch 2003

49. Organic Reactions-Substitution
A halogen is reacted with a saturated hydrocarbon. One of the halogen atoms substitutes one of the hydrogen atoms.
Key to look for – Saturated hydrocarbon reactant and two product.
H H
H C C H
H Cl
H C C H
H H
+ Cl2 UV
+ HCl
J Deutsch 2003

50. Organic Reactions-Polymerization
Polymerization – joining many small molecules together to form a large molecule
A single unit is called a monomer
Many monomers are bonded together to form a polymer
Polymers can be natural or artificial
Natural Polymers
Artificial Polymers
Protein
Polyester
Rubber
Nylon
Cellulose
Styrofoam
J Deutsch 2003

51. Regents Question: 06/02 #49
The process of joining many small molecules
into larger molecules is called
(1) neutralization
(2) polymerization
(3) Saponification
(4) substitution þ
J Deutsch 2003

52. Regents Question: 06/03 #45
Which type of reaction is represented by the equation below?
Note: n and n are very large numbers equal to about 2000.
(1) Esterification (3) saponification
(2) fermentation (4) polymerization þ
J Deutsch 2003

53. Organic Reactions-Esterification
Esterification – making an ester by combining an alcohol with an organic acid
H H
H C C OH
O H
HO C C H H +
H H
H C C O
O H
C C H H
H2O +
J Deutsch 2003

54. Naming Esters (-COOC-)
Esters have a double bonded Oxygen and an –O– bonded to another carbon.
Name the alkyl group that came from the alcohol. Name the acid but drop __ic acid and replace it with ate.
Propanoic acid + pentanol Pentyl propanoate + water
Propanoic acid
1-Pentanol
H H O
H C C C OH
H H
H H H H H
HO C C C C C H
J Deutsch 2003

55. Making an ester by removing water from an acid and an alcohol
Propanoic acid
1-Pentanol
H H O
H C C C O
H H
H H H H H
C C C C C H
H HO
Pentyl propanoate
J Deutsch 2003

56. Name the ester: Methyl ethanoate H O H H C C O C H H H Ethanoate
Acid
Alcohol
Determine which side was the alcohol and which side was the acid by drawing a line through the oxygen in the chain. The side with the double bonded O was the acid.
Alcohol will make you yl if you ate the acid.
J Deutsch 2003

57. Regents Question: 08/02 #56 Given the ester: ethyl butanoate
a. Draw the structural formula for this ester.
b. Determine the gram formula mass of this ester.
C 6 x 12 = 72
O 2 x 16 = 32
H 12 x 1 = 12
116 g
H H H O
H C C C C O
H H H
H H
C C H
Even if you got the structure wrong but you got the correct mass for the structure you drew, you got one point.
J Deutsch 2003

58. Amides (-CON) are made by reacting an organic acid with ammonia or with an amine.
From amine (CH3NH2)
H O
H C C N H
H H
H O H
H C C N C H
H H H
From ammonia (NH3)
J Deutsch 2003

59. Propanoic acid + 1-pentanamine Pentyl propanamide + water
Naming Amides (-CON-)
Amides have a double bonded Oxygen and a Nitrogen.
Name the alkyl group that came from the amine. Name the acid but drop __oic acid and replace it with amide.
Propanoic acid + 1-pentanamine Pentyl propanamide + water
Propanoic acid
1-Pentanamine
H H O
H C C C OH
H H
H H H H H
H2N C C C C C H
J Deutsch 2003

60. Making an amide by removing water from an acid and an amine
Propanoic acid
1-Pentanamine
H H O
H C C C
H H
H H H H H
N C C C C C H
H H H H H H
OH H
Pentyl propanamide
J Deutsch 2003

61. Amino acids have both an amine group and an acid group.
An amino acid is a compound that has an amine group on one side and an acid group on the other.
O R H
HO C C N
H H
R is the only part that changes in different amino acids.
J Deutsch 2003

62. Proteins are polymers of amino
Remove water
O R
HO C C N
H H
O R
C C N H
H H
O R
HO C C N H
H H
J Deutsch 2003

63. Organic Reactions-Fermentation
Fermentation – yeast and bacteria can make ethanol and carbon dioxide by breaking down sugar using an enzyme.
The alcohol can be used to make beer and wine,
The carbon dioxide can be used to make bread rise or make the bubbles in beer and champagne.
Enzyme
C6H12O C2H5OH + 2CO2
J Deutsch 2003

64. Organic Reactions-Saponification
Saponification is a reaction in which a lipid (fat or oil) is used to make soap.
J Deutsch 2003

65. Organic Reactions-Combustion
Burning
Combining with oxygen to produce carbon dioxide and water
Burning Methane CH4 + 2O CO2 + 2H2O
Burning Octane C8H18 +25O CO2 + 18H2O
Burning Ehtanol C2H5OH + 3O CO2 + 3H2O
J Deutsch 2003

66. Regents Question: 08/02 #21 þ In which reaction is soap a product?
(1) addition
(2) substitution
(3) Saponification
(4) polymerization þ
J Deutsch 2003