Organic and Biochemistry organic chemistry: the study of

Organic and Biochemistry organic chemistry: the study of carbon-containing compounds the chemistry of living things biochemistry: (aspirin) -- molecular shape is crucial 3-D structure of salicylic acid 3-D structure of acetylsalicylic acid Carbon is unique among the elements because: -- it can have up to four bonds per C atom single, double, or triple bonds CC C=C

C=C -- it can form REALLY long chains of C atoms -- its bonds are strong Basic Definitions hydrocarbons: compounds containing only __ H and __ C single bonds alkanes: hydrocarbons having only ______ -- ALKANES = FUEL -- very stable; no rxn w/acids, bases, strong oxidizers -- anes are saturated H H H HCCC H H H H H H H H CCCC H HC H H H H H H

structural isomers: same molecular formula, differentbonding arrangements alkenes: hydrocarbons having at least one ____ C=C bond H H C=C H C H H H CH2CHCH3 C=C bond alkynes: hydrocarbons having at least one ____ H H H H

HCC=CCCCH H H H H CH3CC(CH2)2CH3 The simplest alkyne, ethyne (i.e., acetylene) C2H2 is the fuel in oxyacetylene torches. aromatic hydrocarbons: benzene and compounds w/a benzene-related structure 6 C atoms in a planar ring w /tweener bonds (C6H6) -- enes, ynes, and aromatics unsaturated are __________ August Kekule (18291896), who claimed that a dream

gave him insight into the structure of benzene. Finer-Point Definitions C H 5 12 Straight-chain compounds have a single carbon backbone. CH3(CH2)3CH3 CH3CH2CH2CH2CH3 Branched-chain compounds have a main carbon backbone AND one or more branches Substituted compounds have one or more H atoms removed, with other atoms in their place(s) (often halogens) C8H18 Br C5H11Br

Branches and H-replacing atoms/groups are collectively calledsubstituents. Cl H Cl H Cl H CCCCCC H H H H H H Polyvinylchloride (PVC) is a material made of long-chain carbons that have many chloride substituents. Functional group: a characteristic pattern that makes up a portion of a larger mcule -- specific atoms, specific bonding arrangements -- importance: fgs largely determine the behavior of their mcules -- several examples of fgs: alcohols ketones O C OH

O = = OH O C O COOH carboxylic acids OH Many organic compounds are combinations of several categories. C10H21Cl

Cl Cl fg + sub. Br sub. C6H12O2 br. + sub. C6H13OCl C6H11Br OH O fg

OH C9H17OBr Br O fg + sub. + br. Organic Nomenclature Memorize the prefixes that tell the # of C atoms in a chain. 1= 2= 3= 4= 5= 6= 7= 8= 9= 10 = meth

eth prop but pent hex hept oct non dec pent non dec hept Naming Straight-Chain Alkanes 1. Find the longest continuous chain of C atoms. Choose the appropriate prefix. 2. The name ends with ane. Provide the counterpart to the given. (C3H8) propane

heptane (C7H16) Alkanes: modification for substituent hydrocarbon (HC) groups (i.e., branches) 1. Number the longest chain carbons. Start with the end nearest a branch. 2. Name and give the #ed location of each substituent. -- HC substituent groups use the prefixes, but end in yl. 3. List substituents in alphabetical order. Provide each counterpart. 4-ethyl-2-methylhexane (C9H20) 1 2

5-ethyl-3-methyloctane 3 7 5 4 6 (C11H24) 8 Alkanes: modification for non-HC substituents 1. The longest chain MUST contain the substituent. -- example substituents: NO2 nitro NH2 amino

F fluoro Br bromo I iodo 2. Number the chain carbons, starting with the end nearest a substituent. -- A non-HC substituent takes precedence over an HC branch. 3. Name and give the #ed location of each substituent. -- If necessary, choose #s so that their sum is as low as possible. Provide each counterpart. Br 3-bromo-2-chlorohexane Cl 2-ethyl-1,1-diiodoheptane

I I 2-methyl-1-nitrobutane NH2 NO2 NO2 2-amino-6-nitro-3-propyl heptane Alkanes: modification for cycloalkanes -- Use the cyclo- prefix before the word alkane. Provide each counterpart. ethylcyclohexane (C8H16) 1-bromo-1-chloro-2-methylcyclopentane (C6H10BrCl) Br Cl Naming Alkenes and Alkynes 1. The C-chain MUST include the multiple bond.

Use ene or yne, as appropriate. 2. Number so that you get to the multiple bond ASAP. -- The multiple bond takes precedence over branching or substituents. 3. Use di- or tri- right before ene or yne if you have two or three multiple bonds. Polyunsaturated fats and oils contain double and/or triple bonds. Provide each counterpart. 1-butyne (C4H6) 2-butyne (C4H6) 7-methyl-2,4-nonadiene (C10H18) 7-fluoro-6-methyl-3-octyne F

(C9H15F) Cl Cl Cl 3,3,4-trichlorocyclohexene (C6H7Cl3) 4. For geometric isomers (different spatial arrangements of atoms), use cis- (same) or trans- (opposite). Geometric isomerism is possible only with alkenes. Cl C=C CH3CH2 CH2CH3 Cl 3,4-dichloro-trans- 3-hexene Cl

Cl C=C CH3CH2 CH2CH3 3,4-dichloro-cis- 3-hexene Benzene, Phenol, (FEE nahl or fn AHL) and Toluene These are the Big Three aromatic compounds. (C6H6) benzene OH (C6H5OH) phenol CH3 (C6H5CH3) toluene

For phenols and toluenes, the C to which the OH or CH3 is attached is carbon #1. Provide each counterpart. (C6H5Br) bromobenzene Br ethylbenzene (C8H10) 2-propylphenol (C9H12O) OH en NH2 ph OH

am ino H2N - di ol 2,4 iod CH3 trin l ue ne tol u NO2 itro

ot o O2N , 6- - di CH3 2,6 3,4 en I e I NO2 paradichlorobenzene Cl

meta- ortho- l C C l Cl ic d 2- hl e b o r o

e n e z n Cl r lo h ic d 3- e b o e n e z n

Cl b o or z n e l , h 1, 1 c i d For this class, if a benzene ring is 4 , 1 connected to an interior C atom in a hydrocarbon chain, it is called a phenyl (FENN uhl) group. It

looks C6H5. like THIS and has the formula e n e Provide each counterpart. 2-bromo-2-chloro-3-phenylpentane Br Cl 3-amino-3-phenyl-1-butene NH2 NO2 3-nitro-2,4-diphenylhexane Br Br

1,1-dibromo-3-phenyl cyclopentane Alcohols Alcohols contain the hydroxyl group. OH -- low molar mass alcohols are soluble in polar solvents, due to the polar nature of OH -- all alcohols have higher BPs than their parent alkanes (due to HBFs btwn. adj. mcules OH grps) Primary (1o) alcohols have one R group; secondary (2o) have two; R tertiary (3o) have three. RC OH H R H

RC OH RC OH H R Naming Alcohols 1. Without being redundant, specify the location of the OH group(s); the suffix is ol. 2. Use di- or tri- right before ol if you have two or three OHs. Provide each counterpart. 1-propanol OH OH OH 1,1-propane diol 3-ethylphenol OH 3-ethylcyclohexanol OH

5-bromo-2-propyl-6-chloro-1-hexanol HO Br Cl HO OH HO 1,2,4-cyclopentane triol Many pharmaceuticals (including aspirin, shown above) contain hydroxyl groups. Carboxylic Acids O C O C H

O C O O C OH Names end in oic acid, w/the C in the carbonyl being C #1. = = = Esters The C in the carbonyl is C #1. Whatever is attached to the O is named first, then the name ends in oate. =

Aldehydes Names end in al, w /the C in the carbonyl being C #1. Names end in one, w /the C in the carbonyl having the lowest possible number. Functional groups containing the carbonyl group Ketones Provide each counterpart. O 3-hexanone O propylpropanoate O

3-phenylbutanal O F F O H 5,6-difluoro-2-heptanone O 2-ethylpentanal H O 3-propylhexanoic acid OH O methyl-2-methyloctanoate O 4,4,4-trifluorobutanoic acid

O F F F OH Other Functional Groups to Recognize Ethers Amines Amides (EETH erz) (uh MEENZ) (uh MIDZ or AM idz) N caffe-ine = O O CN Organic Reactions

combustion of hydrocarbons OR compounds w/only C, H, and O: products areCO2 and H2O Write the equation for the complete combustion of 2-methyl-2pentene. C6H12 + 9 O2 6 CO2 + 6 H2O Write the equation for the complete combustion of ethylbutanoate. O C6H12O2 + 8 O2 6 CO2 + 6 H2O O substitution: an H atom is removed and something else is put in its place halogen atom replaces an H. -- In halogenation, a _______ Write an equation for the reaction between ethane and chlorine. H H H H

H CCH + Cl2 H CCCl + HCl H H H H If more chlorine is provided, the reaction will produce... H H H H H CCCl + Cl2 ClCCCl + HCl H H H H AND SO ON. Substitution occurs with aromatic compounds, too. Br + Br2 + CH3CH2Cl catalyst catalyst + HBr

+ HCl Ethylbenzene is an important intermediate in the production of styrene which, in turn, is used to make polystyrene. Roughly 25 million tons of ethylbenzene are produced and used every year. addition: a multiple bond is broken and two things are inserted (p(s) is/are broken, s remains intact) H H H H BrCCBr + Br2 C=C H H H H H H H H H CCBr

+ HBr C=C H H H H H H H H H2SO4 H CCOH + H2O C=C H H H H H H H Cl H HCCCCH + Cl2 H CC=CC H H Cl H H

H A specific addition rxn is hydrogenation, in which __ H is added across a multiple C-C bond. -- requires a catalyst (usually a finely-divided _____) metal to rupture the multiple bond H H C=C H H + H2 catalyst H H HCCH H H

Another addition reaction is polymerization. H H H H H H C=C H H H H CCCC C=C H HH H H H H H C=C H H lots of ethylene polyethylene condensation (or elimination, or dehydration): water is a product

_____ -- One reactant provides an __, H the other provides an ___. OH Complex protein molecules are made from condensation reactions of amino acids. NO2 + HNO3 H2SO4 CH3CH2OH + CH3OH alcohol mc alcohol mc + H2O CH3CH2OCH3 + H2O

an ether water -- Condensation reactions polymerize amino acids into...proteins. R O HNCCOH H H R O + HNCCOH H H amino acid #1 amino acid #2 R O R O HNCC NCCOH H H H H a bit of a protein

Note that amino acids have amine groups attached to the C NEXT TO the carboxyl group. + H2O water -- Amides can be formed in condensation rxns between carboxylic acids and amines. Write the equation for the reaction between butanoic acid and ammonia. Ammonia is the simplest amine. O O + NH3 + H2O NH2 OH

carboxylic acid amine amide water Esterification is a condensation reaction between a carboxylic acid and an alcohol. Write the equation for the reaction between butanoic acid and 1-butanol. O + OH HO O O butylbutanoate + H2O (the active substance in the characteristic flavor/odor of pineapple)

Write the equation for the reaction between 3-phenyl-2-propenoic acid and ethanol. O + HO OH O + H2O O ethyl-3-phenyl-2-propenoate (i.e, ethyl cinnamate ) (the active substance in the characteristic flavor/odor of cinnamon) When in doubt, make water. Mr. B

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