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CHM231 Ch.8

What's the functional group of an alcohol? The -OH group bonded to an sp3 hybridized carbon
What's it called if an -OH group is bonded to an sp2 hybridized carbon? phenol or enol
What's the difference between a primary, secondary, & tertiary alcohol? The -OH is on a primary, secondary, or tertiary carbon
If a compound contains two -OH groups, what is it called? A diol
If a compound contains three -OH groups, what's it called? A triol
What's an unsaturated alcohol? An alcohol that contains an -OH and a C=C double bond
Are alcohols polar or nonpolar? Polar
What two bonds in an alcohol are polar covalent? C-O & O-H
What are the only intermolecular forces that occur in nonpolar molecules? London [Dispersion] Forces
What types of molecules do London [Dispersion] forces occur in? Alkanes, alkenes, & alkynes
Are London Forces weak or strong, and how do their strengths change? Weak, and the force increases with the number of electrons in the molecule
Do Dipole-dipole interactions occur on polar or nonpolar molecules? Polar
What type of molecules do dipole-dipole interactions occur on? Haloalkanes
What's a hydrogen bond? An attractive force between a positively-charged H on one atom and a negatively-charged O or N on another atom
What molecules do hydrogen bonds occur on? Alcoholes, amines, amino acids, & carboxylic acids
Which have higher boiling points: Alcohols or hydrocarbons, and why? Alcohols, hydrogen bonds
Which has higher solubility: Alcohols or hydrocarbons, and why? Alcohols, hydrogen bonds
What are hydrophilic molecules? Give examples Molecules that are soluble in water; Polar molecules (like alcohols & acids), hydrogen bonds
What's another name for hydrophobic? Lipophilic
What are hydrophobic molecules? Give examples. Those that are insoluble in water and are soluble in nonpolar solvents; Apolar molecules (like alkanes, alkenes, & alkynes), London forces
What are amphiphilic molecules? Give an example. Molecules with polar and apolar parts, so they can have long hydrophobic chains with polar groups at the end of the chain; Fatty acids
How does chain length affect boiling point and why? As chain length increases, boiling point increases because of increasing London forces
What are two examples of where hydrogen bonds occur in the biology world? DNA & cellulose
How do alcohol's acidity compare to water's? Alcohol's is about the same acidity or slightly weaker than water
As the acid strength increases, the pKa will increase or decrease? Decrease
When a strong acid is present, what does the oxygen atom of an alcohol behave like? A weak base
What does the proton transfer from a strong acid to a weak base create? An oxonium ion
What are two examples of molecules that are amphoteric? Water & alcohols
What does amphoteric mean? A molecule has characteristics of both an acid & a base and can act as either
What do you need to do to convert an alchol to an alkyl halide? Substitute the -OH for a halogen
Is OH- a good or poor leaving group and why? Poor leaving group because it's a strong base
What are the most common reagents that can convert an OH- into a better leaving group? Halogen acids, HX, thionyl chloride, & SOCl2
What mechanism do tertiary alcohols use to react with an HX? Sn1
What are the steps for the reaction of a tertiary alcohol with HX? A proton attaches to the oxygen of the alcohol, an H2O is lost from the oxonium ion giving a tertiary carbocation intermediate, and then a reaction with the halide ion occurs
What mechanism do primary alcohols use to react with an HX? Sn2
What are the steps for the reaction of a primary alcohol with HX? A proton attaches to the OH- giving H2O, and a nucleophilic substitution occurs and H2O is replaced by the halogen ion
What type of reaction in haloalkanes is the reaction of a tertiary alcohol with HX similar to? Sn1
What type of reaction in haloalkanes is the reaction of a parimary alcohol with HX similar to? Sn2
Between Sn1 & Sn2 reactions, which are governed by steric factors & which are governed by electronic factors? Sn1 = electronic, Sn2 = steric factors
What is the most widely-used reagent for converting alcohols to alkyl chlorides? thionyl chloride (SOCl2)
What's splenda and what is it molecularly? An artificial sweetener, sucralose
Of the three, do primary, secondary, or tertiary alcohols require the highest temperature to be converted to an alkene through beta-elimination? Primary alcohols
Do higher reaction temperatures favor nucleophilic substitutions or beta-eliminations in alcohols? Beta eliminations
What's the equation for the change in Gibbs free energy? ΔG = ΔH – TΔS; (ΔG = Gibbs free energy, ΔH = enthalpy, T = temperature [K], ΔS = Entropy [measure of disorder])
What two reactions can occur in the dehydration of alcohols? Nucleophilic substitutions & beta eliminations
What does Zaitsev's rule say about alcohol dehydration? When more than one alkene can be obtained, the more stable alkene will be the major product
How does dehydration of a secondary alcohol occur? Proton transfer from an H3O creates an oxonium ion and a water molecule; H2O is lost & leaves a carbocation intermediate + water; Proton transfer gives an alkene & regenerates the acid catalyst
How does dehydration of a primary alcohol occur? proton transfer of Alcohol + H3O → oxonium ion + H2O; Proton transfer gives H3O + alkene + H2O
Explain hydration-dehydration equilibrium. Adding water to an alkene gives an alcohol, and taking away water from an alchol gives an alkene
Do large amounts of water favor alkene or alcohol formation? Alcohol
Does the scarcity of water favor alkene or alcohol formation? Alkene
What type of molecules can primary alcohols be oxidized to? Aldehydes or carboxylic acids
What type of molecules can secondary alcohols be oxidized to? Ketones
What type of molecules can tertiary alcohols be oxidized to? Actually, oxidation doesn't occur without breaking C-C bonds
What is the most common oxidizing agent of alcohols? Chromic acid, H2CrO4
What molecule do you use to oxidize a primary alcohol to an aldehyde? PCC
What does PCC stand for? Pyridinium chlorochromate
Does PCC oxidize C=C double bonds? No
Are ethers polar or nonpolar, and why? Polar because the C-O bonds are polar-covalent
What type of interactions occur in pure ethers? Dipole-dipole interactions
In solutions with water, what type of molecules are ethers? Hydrogen-bond donors
Compare the boiling points of alkanes, alcohols, and ethers Alcohol > ether > alkanes
Describe the bonds and solubilities of alcohols, ethers, and alkanes Bonds: alcohol = hydrogen bonds, ether = dipole-dipole interactions, alkanes = London forces; solubility: alcohol = in water, ether = mostly in water, alkane = insoluble in water
What's Williamson ether synthesis? When an ether is formed from an organohalide & an alcohol
Why are ethers excellent solvents in which to carry out organic reactions? They have good solvent properties and are generally inert to chemical reactions
What prefix & suffix do cyclic ethers contain? Ox- & -ane
How many atoms are in a ring with the suffix -irane? 3
How many atoms are in a ring with the suffix -etane? 4
How many atoms are in a ring with the suffix -olane? 5
How many atoms are in a ring with the suffix -ane? 6
How are cyclic ethers prepared? Nucleophilic substitution
What's an epoxide? A cyclic ether in which oxygen is one atom of a three-membered ring
How reactive are epoxides to aqueous acid? Readily & very reactive, due to the angle strain in the three-membered ring
What does the reaction of an epoxide with an aqueous acid give? A glycol
What's a thiol? A molecule containing an -SH group bonded to an sp3 hybridized carbon
What suffix is used with thiols? -thiol
What prefix is used with the common names of thiols? Mercapto-
Low-molecular-weight thiols have a __. Give examples Stench (like those present in the scent of skunks & in natural gas odorants)
How are thiols' polarity, and why? Low in polarity because C & S have the same electronegativity
How are thiols boiling points and solubility compared to alcohols? Lower & less soluble than alcohols
How are thiols acidity compared to alcohols? Stronger acids than alcohols
What do thiols + strong bases form? Salts
What are thiols oxidized to? Disulfides
What can disulfides easily be reduced to? Thiols
What does a disulfide refer to? Usually a linked pair of Sulfur atoms
Created by: 817229501