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CHM 106
Organic Chemistry chapter 4
| Question | Answer |
|---|---|
| Organic Chemistry | is the study of Carbon and it's componds (structure, properties, and reactivity of carbon containing compounds, found in fossil fuels, plants, animals skeletons Examples include: gasoline, oil, sugars fossil fuels |
| Hydrocarbon | contains Hydrogen and carbon Therefore hydrocarbons are organic, but all organic compounds are not hydrocarbons |
| Biomolecules-molecules of life | Proteins, carbohydrates, lipids, DNA |
| Why Carbon? | is unique in its ability to form bonds Has 4 valence electrons, so it can bond 4 times to achieve a stable octet Can form a variety of compounds, ability to manipulate and react |
| Organic Chemistry shapes | Can form Chain or rings of various sizes and shapes, can be very large |
| Hydrocarbons are the | simplest C, H only |
| Aliphatic Hydrocarbons - straight chain Saturated and unsaturated are also called | 1. Saturated hydrocarbons - Alkane 2. Unsaturated hydrocarbons - Alkene, Alkyne |
| Aromatic Hydrocarbons | form rings, cyclo- |
| Hydrocarbons derivatives | C,H,O,N,P,S and halogens (N.CHOPS) |
| Aliphatic compounds | are those hydrocarbons that are both open and closed chain compounds. |
| Aromatic compounds are those who have only a ______________chain structure. | closed |
| Molecular Formula | shows the number of atoms of each element in a compound (least informative formula and least expanded form) Ex. Propane = C3H8 |
| Structural Formula | shows the fewest bonds as possible (number of atoms) in each element and the arrangement; most informative formula double bond = Bonds to carbon are shown Bonds to hydrogen are implied Bonds to other elements drawn at the end of chain |
| What is the most expanded formula? | Most expanded form Lewis structure |
| Condensed/Collapsed Formula | combination of both molecular formula and Lewis structure each carbon is written with its attached hydrogens followed by the proper Subscript Ex. Propane = CH3CH2CH3 Straight chain |
| Skeletal structures | are bare bone structure and only shows the bonds between carbon atoms as each of the bond line) Carbon and hydrogen atoms are not shown explicitly All lines are drawn in except those of hydrogen |
| Types of structural formulas | Straight Chain Chain and Branch Cyclic( Ring ) |
| ALKANES: THE SIMPLEST ORGANIC COMPOUNDS | Single bonded hydrocarbons contain hydrogen and carbon These bonds are considered saturated hydrocarbons Maximum number of hydrogen atoms attached |
| Name straight chain alkanes using prefixes (numbers 1-4) | 1 Meth 2 Eth 3 Prop 4 But |
| Name straight chain alkanes using prefixes (numbers 5-10) | 5 Pent 6 Hex 7 Hept 8 Oct 9 non 10 dec |
| Straight-chain alkanes are made up of | carbon atoms joined to one another to form continuous, unbranched chains of varying length. |
| Each compound is given a name that is based on | the number of carbon atoms in its chain. |
| Alkanes general formula | CnH2n+2 |
| Cycloalkanes general formula | CnH2n |
| All alkanes are | non-polar and not radioactive |
| What do alkanes react with ___________and name the reaction | React with oxygen and undergo combustion reaction. Carbon dioxide and water are burned products. Incomplete combustion results in carbon soot and carbon monoxide. |
| Cycloalkanes name shapes and smallest and most common | Cyclo- ring compound , Form long chains also rings Smallest is cyclopropane ring is 3 carbon atoms Most common is five and six carbon rings Name based on the number of carbons with 1 hydrogen Cyclopropane, cyclohexane |
| All alkenes are | nonpolar and do not break down easily / Not water Soluble Lipids and amino acids eg. cyclopropane, cyclobutane, cyclopentane |
| Physical properties of alkanes | The electronegativities of carbon and hydrogen are so similar that when these two elements form covalent bonds, the electrons are shared equally, and the bond is nonpolar. |
| Physical properties of alkanes- composed of | Composed solely of carbon and hydrogen and are nonpolar regardless of their shape. The nonpolar nature of alkanes affects the behavior of these compounds in aqueous systems. |
| Functional Groups of Singly Bonded C - bonds and charges | Bonds are polar, with a partial positive charge on C(+) and partial negative charge (-) on electronegative atom |
| Organic compounds are classified based on | functional groups, this is the reactive part of the compound Rest of the compound is represented with the R group (-R) |
| Heteroatoms | elements other than carbon or hydrogen that are present in organic compounds |
| Functional Groups of Alkane: Alkyl halide Singly Bonded C | C bonded to halogen (C-X) |
| Functional Groups of Alkane: Alcohol Singly Bonded C | C bonded O of a hydroxyl group (C-OH) |
| Functional Groups of Alkane: Ether Singly Bonded C | Two C's bonded to the same O (C-O-C) |
| Functional Groups of Alkane: Amine Singly Bonded C | C bonded to Nitrogen (C-N) |
| Functional Groups of Alkane:Thiol Singly Bonded C | C bonded to SH group (C-SH) |
| Functional Groups of Alkane: Sulfide Singly Bonded C | Two C's bonded to same sulfur (C-S-C) |
| Functional Groups Doubly bonded to C=C (group) | carbonyl |
| Alkanes can be both singly and double bonded to C. One is called _______________ and the other un_____________. | Saturated and unsaturated |
| Functional Groups - carbonyl group: Aldehyde | one hydrogen bonded to H-C-C |
| Functional Groups - carbonyl group: Ketone: | two C's bonded to the C=C-CO |
| Functional Groups - carbonyl group: Carboxylic acid | OH bonded to the C=O |
| Functional Groups - carbonyl group: Ester | CO bonded to the C=O |
| Functional Groups - carbonyl group: Amide | CN bonded to the C=N |
| Functional Groups - carbonyl group: Acid chloride | Cl bonded to the Cl-C=O |
| Alkenes end in -ene | Double bonded hydrocarbons contain double carbon to carbon bond |
| Alkene bonds | These bonds are considered unsaturated hydrocarbons because more than 1 home to carbon atoms(acyclic hydrocarbon) Example: Ethylene (C2H4) C-C=C-C |
| General formula | CnH2n for molecules with one double bond (and no rings) |
| Terpenes | are the primary constituents of essential oils and are responsible for the aroma characteristics of cannabis. |
| Alkynes end in -ynes | Alkynes are unsaturated hydrocarbons that contain carbon-carbon triple bonds. More than one bond between two carbon atoms |
| Alkyne bonds are triple but | shorter and stronger than alkenes |
| Alkynes general formula is | (CnH2n-2) for molecules with one triple bond (and no rings). |
| Aromatics / Phenyl Alkyne group | Cyclic structure like ; have an aroma (aromatic compounds like spearmint and peppermint. Unsaturated closed six-membered ring- usually stable and not very reactive |
| Aromatics general formula is | C4r+2H2r+4 |
| Bonds between carbon in an aromatic is = (how many) | Equal double bonds and equal single bonds |
| Benzene exhibits | resonance. (Sharing of electrons) aromaticity also exhibited |
| Lipids are | Fatty Acids |
| Saturated and unsaturated have the same meaning | carbon-carbon bond. |
| Fats may be saturated (having single bonds) or unsaturated (having double bonds). Unsaturated fats may be _________(hydrogens in same plane) or______ (hydrogens in two different planes). | cis or trans |
| Monounsaturated bonds have | one double |
| Polyunsaturated bonds have | two or more double |
| Fatty acids aka lipids are mainly | nonpolar biomolecules mostly made up of hydrocarbon |
| Saturated fatty acids are long | straight-chain, alkane like, with a carboxylic acid functional group at one end. (12-22 C atoms- mostly even numbers) |
| Nomenclature : Straight-chain alkanes | are made up of carbon atoms joined to one another to form continuous, unbranched chains of varying length |
| Each compound is given a name that is based on | the number of carbon atoms in its chain. |
| Nomenclature :Alkanes that do not have their carbon atoms connected in a single continuous chain are called | branched-chain alkanes. |
| The IUPAC nomenclature rules provides a ____________ ___________ for any organic compound and ensure that every compound has just one correct systematic name. | unique name |
| All of the millions of organic compound names have three basic parts: | Substituents- Attachments Parent Name - Number of carbons in the longest continuous chain Suffix- Family name Substiuents + Parent name + Suffix |
| Naming Branched Alkanes | Identify the longest cont. chain of carbons. Identify the substituents to the main chain that were not part of the parent chain. Number the parent chain starting at the end nearest to the subs. Assign a number, (ABC order beginning name) |
| Naming Branched Alkanes - name change | These are the alkyl groups for branched alkanes. -Ane changes to -yl |
| Haloalkanes | Halogens are common substituents on alkane chains. These are also called alkyl halides. The substituent names of the halogens are fluoro, chloro, bromo, and iodo. |
| Rules for naming haloalkanes | The rules for naming haloalkanes are the same as those for naming branched-chain alkanes, with the halogen being the substituent. |
| Nomenclature of cycloalkanes: The rules for determining the IUPAC names for cycloalkanes are the same as those for branched-chain alkanes, with a couple of modifications: | Ring is parent chain (as long as it has more carbon that any other substituents Identify the substituent Number the carbons in the ring. Carbon 1 will always have a substituent Assign a number to the substituents |
| Isomer | Molecules having the same molecular formula but different connectiviuty or arrangement , Has to have four or more carbons |
| Structural isomers | two molecules have the same molecular formula but different connections to atoms, single atoms bonds in a non cyclic compound |
| Conformational isomer or conformer | not different compounds; single bonds can rotate and make molecules look different but are the same molecule |
| Cis-Trans Stereoisomers occur where? | occurs in alkenes |
| Stereoisomers | two molecules have the same molecular formula and the same attachments to skeleton bt have different arrangement |
| Cis - | isomer substituents at opposite end of C=C, are on opposite sides of bond |
| Trans - Stereoisomers | stereoisomer molecule; opposite from each other Unsaturated fatty acids are C=C, only cis alkenes |
| Omega number indicates | carbon position of double bond in structure of fatty acid (ω- omega) |
| Essential fatty acids- can not be produced | by our bodies, component in fats and oils in triglycerides |
| Enantiomers- | same molecular formula and same connectivity but non-superimposable mirror image, Known as chiral. |
| The molecule is said to be chiral if | the image of the molecule cannot be superposed on its mirror image by any combination of translations or rotations. |
| How to determine Chiral center | Locate tetrahedral carbons with four atoms bonded to them Determine if two or more hydrogens are bonded to the tetrahedral carbons- if yes then they can NOT be chiral center |
| Diastereomers | non-mirror image and non-identical stereoisomers on one another |
| enantios in greek means meros in greek means (together make up enantiomers) | the Greek word for opposite Greek word for part |
| Consequences of Chirality - Thalidomide | medication given for morning sickness. Alleviated symptoms; however cause birth defects such as shortened limbs or no limbs. |
| resonance | when more than one correct model exists for the electron distribution of a molecule. |
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