organic compounds. organic halides a hydrocarbon in which one or more hydrogen atoms have been...
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Naming Organic Halides Consider halogen as a branch. Properties of Organic Halides Halogen makes the molecule more polar, increasing strength of the intermolecular forces –Higher boiling points than their corresponding hydrocarbons –More soluble in polar solvents Molecules with more halogens are more polarTRANSCRIPT
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Organic Compounds
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Organic Halides• A hydrocarbon in which one or more
hydrogen atoms have been replaced by halogen atoms
• Freons (chlorofluorocarbons) in refrigeration and air conditioning
• Teflon (polytetrafluoroethane)• DDT, PCBs
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Naming Organic Halides• Consider halogen as a branch.
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Properties of Organic Halides• Halogen makes the molecule more polar, increasing
strength of the intermolecular forces– Higher boiling points than their corresponding hydrocarbons– More soluble in polar solvents
• Molecules with more halogens are more polar
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Preparing Organic HalidesRecall: Substitution reaction produce halides in alkanes and aromatic hydrocarbons
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Preparing Organic HalidesRecall: alkyl halides are produced in halogenation reactions
with hydrocarbons
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Elimination Reactions• Preparing alkenes from alkyl halides• Most common method of preparing alkenes• Alkyl halides can eliminate a hydrogen and a halide ion
from adjacent carbon atoms forming a double bond.• Presence of a hydroxide ion is required
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Alcohols• Organic compounds containing a hydroxyl group -OH• E.g. ethanol, cholesterol, retinol (vitamin A)Naming:• -ol suffix e.g. methane + OH = methanol
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Polyalcohols• Alcohols containing more than one -OH
group• -diol, -triol suffix• Or hydroxy prefix
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1,2-dihydroxyethane 1,2,3-trihydroxypropane
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Properties of Alcohols• More polar and can hydrogen bond
– Higher boiling points– More soluble in polar solvents
• Long-chain alcohols are nonpolar (hydrocarbon portion) and polar (-OH)– Ideal solvents in organic reactions because
they will dissolve both polar and nonpolar compounds
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Hydration Reactions• Alkene + water --> alcohol• Follows Markovnikov’s rule
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Combustion of AlcoholsQuickTime and aᆰ
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Elimination ReactionsDehydration (Condensation) Reactions:• Under certain conditions alcohols can decompose to
produce alkenes and water• A catalyst (sulfuric acid) removes a hydrogen atom and a
hydroxyl group from neighbouring carbons• Resulting in C=C and H2O
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Ethers• Molecules with C-O-C group• More polar than hydrocarbons • But, unlike alcohols, ethers cannot hydrogen bond
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Naming:• Add oxy to the prefix of the smaller hydrocarbon group and
join it to the alkane name of the larger hydrocarbon group• E.g. CH3-O-C2H5 is methoxyethane
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Condensation Reactions• When two alcohols combine, an ether and water are formed
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Aldehydes and KetonesKetone: Molecule with a carbonyl group (C=O) between two
carbon atoms. Alkane name with -one suffix
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Aldehyde: Molecule with a carbonyl group (C=O) on a terminal carbon. Alkane name with -al suffix
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Properties of Aldehydes and Ketones
• Lower boiling point and less soluble in water than alcohols (no -OH)
• More polar than hydrocarbons (higher boiling points and more soluble)
• Good solvents (both polar and nonpolar)
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Oxidation Reactions• Alcohol + an oxidizing agent (removes
electrons) to form an aldehyde or ketone and water
• The oxidizing agent removes two H-atoms (one from the -OH group and one from the adjacent carbon) resulting in C=O and H2O
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Oxidizing agent
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Hydrogenation Reactions• The C=O double bond can undergo an addition reaction with
hydrogen to form an -OH group.• Aldehydes always produce 1˚ alcohols
• Ketones always produce 2˚ alcohols
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Carboxylic Acids• Molecules with a carboxyl group -COOH• E.g. lactic acid, citric acid
• Alkane name with -oic acid• E.g. methanoic acid
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Properties of Carboxylic Acids
• Polar and can hydrogen bond• Similar properties to alcohols (smaller
members are soluble in water, larger members are insoluble)
• pH < 7 (H-atom in -OH group)
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Oxidation ReactionsRecall: A 1˚ alcohol can be oxidized to form an aldehyde.
An aldehyde can be further oxidized to form a carboxylic acid
A ketone cannot be oxidized because there is mo free H-atom
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Oxidation Reaction
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EsterficationRecall: acid + base --> salt + water (neutralization reaction)
Carboxylic acid + alcohol --> ester + water
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Properties of Esters• Similar to carboxylic acids, but lacking -OH group
• Esters are less polar (less soluble in water), lower boiling points (no H-bonds)
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Naming Esters• 1st part is the name of the alkyl group in the alcohol• 2nd part is the ending of the acid name changed from -oic
to -oate
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Amines• An ammonia molecule in which one or more H-atoms are
substituted by alkyl or aromatic groups
Naming:• Amino + alkane name OR• Alkyl group + amine
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Naming 2˚ and 3˚ Amines• N- prefix used for the substituted groups on the nitrogen
atom• Alkyl groups are listed alphabetically
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N,N-dimethyl-2-aminopropane
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Properties of Amines• N-C, and N-H polar bonds• H-bonding occurs but N-H is less polar than
O-H
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Synthesizing Amines from Alkyl Halides• Alkyl halide + ammonia --> 1˚ amine + HX
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• Alkyl halide + 1˚ amine --> 2˚ amine + HX
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• Alkyl halide + 2˚ amine --> 3˚ amine + HX
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Synthesizing Amines from Alkyl Halides
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Amides• Similar to esters, except N instead of O
Recall: Carboxylic acids + alcohols --> esters + water
Carboxylic acids + ammonia/1˚/2˚ amines--> amides + water
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Naming Amides• 1st part is the name is from the amine• 2nd part is the ending of the acid name changed from -oic
to -amide• Alphabetical order with N- groups
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N-ethyl propanamide
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Summary
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