Slide 1 / 123 Slide 2 / 123 Organic Chemistry New Jersey Center - PDF document

Slide 1 / 123 Slide 2 / 123 Organic Chemistry New Jersey Center for Teaching and Learning Progressive Science Initiative Carbon and the Molecular Diversity of Life This material is made freely available at www.njctl.org and is intended for the non-commercial use of students and teachers. These materials may not be used for any commercial purpose without the written permission of the owners. NJCTL maintains its website for the convenience of teachers who wish to make their work available to other teachers, participate in a virtual professional learning community, and/or provide access to course materials to parents, students and others. Click to go to website: www.njctl.org Slide 3 / 123 Slide 4 / 123 Organic Chemistry Organic Chemistry Organic chemistry is the chemistry of carbon Organic compounds range from simple molecules to compounds. colossal ones Carbon is the backbone of biological molecule Carbon has the ability to form long chains. Most organic compounds contain hydrogen atoms in Without this property, large biomolecules such as addition to carbon atoms proteins, lipids, carbohydrates, and nucleic acids could not form. Stearate C 17 H 36 O 2 Slide 5 / 123 Slide 6 / 123 Organic Chemistry 1 Organic chemistry is a science based on the study of A Carbon has four valence electrons to make covalent bonds functional groups. B vital forces interacting with matter. Carbon atoms can form diverse molecules by bonding to four C carbon compounds. other atoms water and its interaction with other D kinds of molecules. Electron configuration is the key to an atom’s characteristics E inorganic compounds. Electron configuration determines the kinds and number of bonds an atom will form with other atoms

Slide 7 / 123 Slide 8 / 123 3 How many electron pairs does carbon share in order 2 Which property of the carbon atom gives it to complete its valence shell? compatibility with a greater number of different elements than any other type of atom? A 1 B 2 A Carbon has 6 to 8 neutrons. B Carbon has a valence of 4. C 4 C Carbon forms ionic bonds. D 6 D A and C only E 8 E A, B, and C Slide 9 / 123 Slide 10 / 123 4 What type/s of bond/s does carbon have a 5 Organic chemistry is currently defined as tendency to form? the study of compounds that can be made only by A A Ionic living cells. Hydrogen the study of carbon compounds. B B Covalent C C the study of vital forces. D A and B the study of natural (as opposed to synthetic) D compounds. A, B and C E the study of hydrocarbons. E Slide 11 / 123 Slide 12 / 123 Hydrocarbons Aliphatic hydrocarbon: Alkanes Hydrocarbons are compounds made up of carbon and hydrogen Hydrocarbon chains made up of all SINGLE carbon bonds atoms. There are two major categories: Aliphatic and Aromatic They are also known as saturated hydrocarbons Aliphatic hydrocarbons : compounds with carbon atoms They are “saturated” with hydrogens connected in a straight chain Name uses the ending -ane Aliphatic compounds consist of three classes of compounds: Examples: Methane, Propane, Butane, Octane · Alkanes · Alkenes · Alkynes Aromatic hydrocarbons : compounds with carbon atoms connected to form cyclic structure and with an aroma (smell or odor)

Slide 13 / 123 Slide 14 / 123 Aliphatic hydrocarbon: Alkanes Aliphatic hydrocarbon: Alkanes The general formula C n H 2n+2 n = number of carbon atoms Formula Name Formula Name CH 4 Methane Hexane C 2 H 6 Ethane Heptane C 3 H 8 Propane Octane C 4 H 10 Butane Nonane C 5 H 12 Pentane Decane (The students can fill this) Slide 15 / 123 Slide 16 / 123 Aliphatic hydrocarbon: Alkanes Aliphatic hydrocarbon: Alkanes Straight chain alkanes: An alkane that has all its carbons connected in a row. CH 3 -CH 2 -CH 3 Branched chain alkanes: An alkane that has a branching connection of carbons. CH 3 Hydrocarbons are non polar. All C-H bonds are nonpolar. CH 3 -CH-CH 2 -CH 3 As the number of electrons in the molecule increases ( larger molecules), it would be easily polarizable and hence the LD forces increases. This increases the bpt. of the higher alkanes. Slide 17 / 123 Slide 18 / 123 Alkanes Alkanes: Ethane Isopentane Pentane Condensed formula Structural formula CH 3 - CH 3 H H CH 3 - CH 2 - CH 2 - CH 2 - CH 3 CH 3 - CH(CH 3 ) - CH 2 - CH 3 H C C H H H Neopentane C(CH 3 ) 4 Branched chain Branched chain

Slide 19 / 123 Slide 20 / 123 Alkenes 6 What is the reason why hydrocarbons are not soluble in water? Alkenes have at least one 1 double bond between two carbon atoms. The majority of their bonds are polar covalent A carbon to hydrogen linkages General formula: C n H 2n The name uses the ending -ene The majority of their bonds are nonpolar covalent B carbon to hydrogen linkages The first member would be They are hydrophilic C C 2 H 4 - Ethene (from 2 carbon parent, ethane) Ethene C 3 H 6 - Propene They exhibit considerable molecular complexity D and diversity E They are lighter than water Slide 21 / 123 Slide 22 / 123 Alkynes Aliphatic hydrocarbons Alkyne general formula: C n H 2n-2 Ball and stick Space filling Structural Molecular formula model model formula They must have at least one triple bond The name uses the ending -yne C 2 H 2 Ethyne or commonly known as acetylene C 3 H 4 Propyne or propylene Ethyne Slide 23 / 123 Slide 24 / 123 Cycloalkanes Aromatic hydrocarbons Carbon can also form ringed structures. They have benzene ring structure (hexagon) and a particular aroma. Five and six-membered rings are most stable. CH 3 They can take on conformations in which their bond angles are very close to the tetrahedra angle. Smaller rings are quite strained Benzene Toluene (methyl benzene)

Slide 25 / 123 Slide 26 / 123 7 Hydrocarbons 8 Which of the following hydrocarbons has a double bond in its carbon skeleton? A are polar. A C 3 H 8 B are held together by ionic bonds. B C 2 H 6 contain nitrogen. C CH 4 C contain only hydrogen and carbon atoms. D C 2 H 4 D are held together by hydrogen bonds. E E C 2 H 2 Slide 27 / 123 Slide 28 / 123 9 The gasoline consumed by an automobile is a 10 Hydrocarbons containing only single bonds fossil fuel consisting mostly of between the carbon atoms are called __________. aldehydes alkenes A A amino acidd alkynes B B alcohols C aromatics C hydrocarbons D alkanes D thiols ketones E E Slide 29 / 123 Slide 30 / 123 11 Which is the formula of an alkane? 12 Hydrocarbons containing carbon-carbon triple bonds are called________. C 10 H 10 A alkenes A C 10 H 18 B alkynes B C 10 H 20 C aromatics C C 10 H 22 D alkanes D C 10 H 24 E ketones E

Slide 31 / 123 Slide 32 / 123 13 Which is the formula of an alkyne? 14 The molecular geometry of each carbon atom in an alkane is ________. C 10 H 10 A octahedral A C 10 H 18 B square planar B C 10 H 20 C trigonal planar C C 10 H 22 D tetrahedral D C 10 H 24 E trigonal pyramidal E Slide 33 / 123 Slide 34 / 123 An alkene has at least one ________ and has the 15 The general formula of an alkane is _______. 16 general formula ______. A C 2n H 2n+2 C-C single bond, C n H 2n+2 A B C n H 2n C-C double bond, C n H 2n B C n H 2n+2 C C-C triple bond, C n H 2n C C n H 2n-2 C-C double bond, C n H 2n-2 D D C n H n E C-C triple bond, C n H 2n-2 E Slide 35 / 123 Slide 36 / 123 17 The compound below is an _________. 18 Gasoline and water do not mix because gasoline is __________. alkyne A less dense than water A alkene B less viscous than wtaer B C alkane nonpolar and water is polar C aromatic compound D volatile and water is not D olefin E polar and water is nonpolar E

Slide 37 / 123 Slide 38 / 123 19 Which substance would be the most soluble in 20 ________ could be the formula of an alkene. gasoline? C 3 H 8 A water A C 3 H 6 B B NaNO 3 C 6 H 6 C HCl C D C 17 H 36 hexane D CH 8 E NaCl E Slide 39 / 123 Slide 40 / 123 Isomers Isomers Hydrocarbons exhibit a phenomenon called isomerism- existence of different molecular arrangement but same formula. Isomers are compounds with the same molecular formula but different structures and properties: Structural isomers have different covalent arrangements of their atoms Structural Isomers Geometric isomers have the same covalent arrangements but differ in spatial arrangements Enantiomers are isomers that are mirror images of each other Slide 41 / 123 Slide 42 / 123 Isomers Isomers cis isomer: trans isomer: The The two CH 3 two CH 3 are on are on the Enantiomers are opposite sides. same side. isomers that are nonsuperimposable mirror images Enantiomers (optical isomers) Enantiomers differ in spatial arrangement around an asymmetric Geometric Isomers carbon, resulting in molecules that are mirror images, like left and right hands. The two isomers are designated the L and D isomers from the Latin for left and right ( levo and dextro ). Enantiomers cannot be superimposed on each other.