Organic Chem ACS Test Review

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What are characteristics of organic compounds
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most are insoluble in water. Most are liquid or low melting solids at room temp and few are gases.
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What is a functional group?
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atom/group within a molecule that has a characteristic physical and chemical behavior
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What is the general rule for isomers?
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all hydrocarbons except methane is that carbon must be bonded to at least 1 carbon. Carbon atoms makes backbone.
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What is the general formula for alkanes?
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CnH2n+2
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What is an isomer?
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compounds with same molecular formula, but with different connection.
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What are functional group isomers?
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Molecular formula contains atoms other than carbon and hydrogen, the consitutuional isomer is obtained.
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How do you name Alkanes?
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Named by counting the # of carbon atoms and adding family suffix -ane. No prefix needed.
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What are the 4 possible substitution patterns?
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Primary, Secondary, Tertiary, and Quaternary
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What are some properties of alkanes?
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The only intermolecular forces influencing them are weak London dispersion forces. First 4 alkanes are gases at room temp. 5-15 are liquids. 16 or more are low melting, waxy solids. Insoluble in water. odorless, colorless, tasteless, and nontoxic
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What is the Curved Arrow formalism?
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Movement is depicted by curved arrows. Single is 1 electron. Double is movement of 2 elections
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What is combustion?
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Alkanes reacting with an oxygen. Complete combustion forms CO2 and H2O. Releases a lot of heat. Incomplete can create carbon monoxide and carbon with soot.
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What is Halogenation?
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Replacement of an alkane hydrogen by a chlorine or bromine initiated by heat or light.
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What are properties of cycloalkanes?
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Cycloprotane and cyclobutane are gases at room temp. Non polar, insoluble in water and flammable. More rigid and less mobility.
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How do you name cycloalkanes?
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use cycloalkane name as parent. Identify and number substituents. Go alphabetical priority. Give substituents lowest number
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Describe Saturated and Unsaturated in alkanes, alkenes, and alkynes.
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Alkanes are saturated because they have many hydrogen’s as possible. Alkenes and Alkynes are unsaturated because they contain carbon-carbon multiple bonds.
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How do you name Alkenes or Alkynes?
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Name the parent compound. Longest chain containing double/triple bonds. Add suffix -ene or -yne. Then number carbon atoms in the mainchain so that those with multiple bonds have the lowest index numbers possible
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What is Ethylene?
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2 carbon alkene called ethene
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What is Propylene?
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3 carbon alkene called propene
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What is Isoprene?
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4 carbondiene, or 2-methyl-1,3-butadiene
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What is acetylene?
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The simplest alkyne. Should be known as ethyne.
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What are properties of alkenes or alkynes?
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less dense than water, non-toxic, flammable. Alkenes display cis-trans isomerism. Chemically reaction at multiple bond. Non-polar, not soluble in water.
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What is an addition reaction?
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Where a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that only single bonds.
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What is an elimination reaction?
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Saturated reactant yields an unsaturated product by losing.
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What is a substitution reaction
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Atom/group of atoms in a molecule is replaced by another atom/group
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What is an rearrangement reaction
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molecule undergoes bond reorganization to yield an isomer
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What is Hydrogenation
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In presence of a metal catalyst to yield the corresponding alkane product
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What is Markovnikovs Rule?
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The major product arises from the H attaching to the double bond carbon that has the largest # of H atoms directely attached to it, and the x attaching to the carbon with less #.
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What is Hydration?
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Alkenes wont react with pure water. If small amounts of a strong acid catalyst is added, an addition reaction will happen and yield an alcohol.
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What is a benzene?
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Hexagon with 3 double bonds.
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What are properties of benzene?
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They are much less reactive than alkenes and normally don’t undergo addition reactions. Nonpolar, insoluble in water, volatile, and flammable.
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What is Resonance?
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Each C-C bond is intermediate between a single bond and double bond.
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How to name substituents on Benzene Rings.
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Ortho-1,2. Meta-1,3. Para-1,4.
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What is the systemic name of toluene?
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Methylbenzene
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What is the systemic name of phenol?
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Hydroxybenzene
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What is the systemic name of Ciniline?
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Aminobenzene
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What is a phenyl?
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When a benzene is a substituent group.
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What is Nitration?
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Substitution of nitro group NO2 for a H.
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What is Halogenation?
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Substitution of a halogen group, X, for a H.
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What is sulfonation?
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Substitution of sulfonic acid group, SO3H, for a H.
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What is an alcohol?
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Has an -OH group bonded with a saturated, alkane-like carbon atom.
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What is a phenol?
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OH attached to a benzene ring.
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What is an Ether?
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Oxygen bonded with 2 organic groups
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What are properties of Alcohols?
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Polar, hydrogen bonding occurs, straight chain alcohols with up to 12 carbons are liquid. Hydrophilic and hydrophobic parts. Has a larger hydrophobic part.
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Describe Methyl Alcohol.
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Methanol. Wood Alcohol. Used as a solvent and start of formaldehyde. Colorless, miscible in water, and toxic. Causes blindness and death
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Describe Ethyl Alcohol.
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Enthanol. Grain Alcohol. Produced in fermentation. Ethyl alcohol is made by hydration of ethylene.
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Describe Isopropyl Alcohol.
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Rubbing alcohol. Less toxic than methanol but more toxic than Ethanol. Skin Cleanser
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Describe Ethylene Glycol.
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It is a diol. Used as engine antifreeze and coolant. Highly toxic and has a slightly sweet taste.
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Describe Glycerol.
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Useful in food so it is sweet. Used as moisturizer and solvent. Extremely viscous fluid. Provides back bone for animal fats or veggie oils.
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How do you name alcohols?
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Name parent chain, Number carbons, and write name
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What are diols?
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2 OH groups on adjacent carbons.
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What is Dehydration?
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Alcohols undergo a loss of water on treatment with a strong acid. Completed by heating. OH group is lost from 1 carbon and H is lost from an adjacent carbon to yield an alkene
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What is Zaitsevs Rule?
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More substituted alkene will be favored, result of equilibrium process that is operating; the less table form is more likely to revert to the cation.
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What is Oxidation?
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Occurs when primary and secondary alcohols are converted into carbonyl-containing compounds by an oxidizing agent. Increase in C-O bonds and or decrease in C-H bonds
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Primary alcohols are converted to…
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Aldehydes under controlled conditions. or carboxylic acids, if in excess of oxidant is used.
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Secondary alcohols are converted to…
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Ketones
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Describe Phenols
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Alcohol on a benzene ring. Used as a medical antiseptic that numbs skin. Name ends with phenol not benzene
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What are properties of phenols?
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Somewhat water soluble. higher boiling and melting points. Less soluble in water than alcohols.
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Describe the acidity of alcohols and phenols.
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Very weak acidity because of the positively polarized OH hydrogen. They dissolve slightly in solution and establish equilibria between neutral and anionic forms. Phenols are 10,000 more acidic than water
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What is an alkoxide ion?
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a strong base as a hydroxide ion. (Anion of alcohol)
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How do you name ethers?
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Named by identifying the two organic groups and adding the word ether
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What are properties of ethers?
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do not react with acids or bases. Highly flammable. In standing air, many ethers form explosive peroxides. Found in plant oils and in nature
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How is the systemic name formed for a thiol?
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Adding thiol to the parent hydrocarbon name
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What are characteristics of thiols?
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most outstanding characteristic is their odor. React with mild oxidizing agents to yield disulfides. Two thiols join, the H is lost, and bond forms between sulfers.
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What are Amines?
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one or more organic groups bonded to nitrogen. Organic derivatives of ammonia.
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What is an amino group?
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NH2
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How to name an amino group as a substituent
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Amino- is used as a prefix in the name of the compound
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What are anilines?
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the simplest aromatic amine
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What are properties of Amines?
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can form H bonds with water. up to 6 carbons are soluble in water. Many have strong odors. They are weak bases
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What are heterocycles?
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Compounds with atoms other than C in a ring
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Describe the basicity of amines
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An ammounium ion is a positive ion formed by addition of hydrogen to amine.
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How are alkylamine cations named?
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Replaceing ending -amine with -ammonium
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What is an ammounium salt?
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ionic compound composed of an ammonium cation and an anion. an amine salt.
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How are ammonium salts named?
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combining the ion names.
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What are properties of ammonium salts?
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Odorless, white, chrystalline solids that are more soluble than neutral amines.
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What is an alkaloid?
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Naturally occurring Nitrogen-containing compounds isolated from a plant; usually basic, bitter, and poisonous.
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What are the 5 carbonyl groups?
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Aldehyde, Ketone, Carboxylic Acid, Ester, and Amide
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What is an aldehyde?
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compound that has a carbonyl group bonded to at least one H. RCHO. Always are the end of a carbon chain.
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What is a ketone?
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A compound that has a carbonyl group bonded to two carbons in organic groups that can be the same or different. RCOR. Always within a carbon.
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How do you name aldehydes?
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End in -aldehyde. Systemic name is replacing the final -e with -al. When substituents are present, the chain is numbered beginning with carbonyl carbon
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How do you name ketones?
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Replace final -e with -one. numbering chain begins at end closest to ketone
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Boiling points in order of highest to lowest
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Alcohols, amines, aldehydes/ketones, alkanes/alkenes/alkynes
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Describe Formaldehyde
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colorless gas with an odor. formed by incomplete combustion of hydrocarbon fuels and partly responsible for irritation by smog-air
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Describe Acetaaldehyde
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Sweet smelling but narcotic. Flammable liquid formed by the oxidation of ethynol.
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Describe Acetone
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A super solvent. Dissolved most organic compounds and is miscible with water. Volatile.
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Describe the oxidation of aldehydes
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Alcohols can be oxidized to aldehydes or ketones. Aldehydes go to carboxylic acid. Aldehyde oxidation is H bonded to carbonyl carbon is replaced with OH group
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What is Tollens Reagent
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Consists of silver ion in aqueous ammonia. Treatment of aldehyde with reagent rapidly yeilds the carboxylic acid anion and metallic silver
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What is Benedicts reagent.
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It contains blue copper. If aldehyde is present, it will turn red.
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Describe Hemiacetal formation.
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Aldehydes and ketones undergo addition reaction in which an alcohol combines with the carbonyl carbon and oxygen. Hemis have both an alcohol-like OH group and an ether like OR group bounded to a once was the carbonyl carbon atom. Often too unstable to be isolated.
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Describe Acetal formation
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Small amount of acid catalyst is added to reaction of alcohol with aldehyde or ketone the hemiacetal initially formed is converted to an alcohol. Acetal is a compound that has 2 ether like groups bonded to what was the carbonyl carbon group
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What is Acetal Hydrolysis
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Reversal required an acid catalyst and a large quantity of water to drive the reaction back towards aldehyde or ketone
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What is a carbonyl group substitution reaction?
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Group -Z replaces the group bonded to the carbonyl carbon atom.
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Describe Carboxylic Acids
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They surrender the H of the carboxyl group to bases and establish acid-base equilibria in aqueous solutions
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What are properties of carboxylic acids
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Form H-bonds with each other. Up to 9 carbons, they are liquid. Water soluble up to 4 carbons.
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How do you name Carboxylic Acid?
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Replacing -e at end with -oic acid
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How do you name Acetyl Groups?
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replace the -ic at the end of acid with -oyl.
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How are unsaturaed acids named?
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Ending with -enoic
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Describe Esters
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Simple esters are lower boiling points than acids from which they are derived. Simple are colorless, volatile with a pleasant odor
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How do you name esters?
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Name the alkyl group R in the ester group. Then name of the parent acid group with family name ending -ic acid replaced by -ate
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What are amides?
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Compounds with nitrogen directly attached to a carbonyl carbon.
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What are properties of amides?
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soluble in water and organic solvents. No basic like amines. Low-molecular weight unsubstituted are solids.
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What are properties of Carboxylic Acids, Esters and Amides?
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All undergo carbonyl group substitution reactions. Esters and amides made from carboxylic acids.
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Describe Acetic Acid
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Primary organic compound of vinegar.
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Describe Citric Acid
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Produced by almost all plants and animals during metabolism. Commonly used to buffer pH. Very soluble in water. White, crystalline solid.
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Describe the acidity of Carboxylic acids
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They are weak acids that establish equilibria in aqueous solutions with caroxylate anions.
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How are carboxylate anions named?
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By replacing the -ic ending in the carboxylic acid name with -ate
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How is strength of an acid measured?
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By its dissociation constant. (Ka) smaller value of Ka, the weaker the acid.

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