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155 Cards in this Set
- Front
- Back
What is a phenol?
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an organic compound that includes a benzene ring attach to a hydroxyl (OH)
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What do you call an organic compound with a hydroxyl attached to a benzene ring?
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phenol
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What do you call a compound that includes a C6H6 attached to an OH?
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phenol
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What is the difference between a phenyl and a phenol?
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A phenol is an organic compound that includes a hydroxyl (OH) attached to a benzene ring. A phenyl is what you call a benzene ring when it is a substituent on a carbon chain.
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What do you call the group contained in thiols? What is its formula?
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sulfhydrl (-SH)
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Sulfhydrls are found in what family of compounds?
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Thiols
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Compounds with -SH are part of what group? What family is this group found in?
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sulfhydrls, found in Thiols
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how do you change the name of a compound to indicate that it's an alcohol?
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Replace the suffix with "ol"
e.g., Methane becomes "methanol" Methanol = CH3-OH |
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How do you name thiols?
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Replace the "ane" suffix of the compound with "-ethiol"
E.g., Ethanethiol = CH3-CH2-SH |
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What type of compound is CH3-CH2-CHSH-CH2-CH3? What is the IUPAC name for this particular compound?
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It is a Thiol because of the SH. The IUPAC name would be 3-sulfhydrlpentane.
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Carbons are classified by the number of carbon atoms attached to what?
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the carbon atom bonded to the hydroxyl (OH) group.
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What is the difference between a primary, secondary and tiertiary alcohol?
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Primary, secondary and tertiary alcohols have 1, 2 and 3 additional carbon atoms bonded to the carbon that the OH is attached to.
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What family and class is the compound CH3-CH2-C2H4-OH?
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It is a secondary alcohol.
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What is another name for 2-bromophenol?
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ortho-bromophenol or o-bromophenol
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What is another name for 3-chlorophenol?
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meta-chlorophenol or m-chlorophenol
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What do you call a benzene ring with a hydroxyl at 1 and ethyl at 4?
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4-ethylphenol or para-ethylphenol, or p-ethylphenol
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What is a cresol?
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A methylphenol.
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What is an example of a cresol?
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any benzene ring with OH and CH3 attached at different points on the ring.
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What would para-cresol look like?
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a benzene ring with OH attached at point one (so, its a phenol) and a CH3 attached at point 4 opposite the OH
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What is a benzenediol?
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a benzene ring with two hydroxl (OH) groups attached
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What is the IUPAC name for a chain of 5 carbons with a CH2-CH3 attached at spot 4, an iodine at point 5, and an OH attached at point 2?
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4-ethyl-5-iodo-2-pentanol
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What do you call benzene ring with both a hydroxide and methyl group attached?
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cresol
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What do you call a benzene ring with two OH groups attached?
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benzenediol
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What do you call a benzene ring with OH groups attached at 1 and 3?
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1,3-benzenediol, aka resorcinol
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How do you name thiols?
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Add the suffux "thiol" to the end. So, propane becomes propanethiol
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What is the IUPAC name for CH2=CH-CH2-SH?
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2-propene-1-thiol
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What is the common name of CH3-OH?
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Methyl alcohol
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What is the common name of Pentanol?
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Pentyl alcohol
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What do you call CH3-CH2-CH2-CH2-SH?
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butanethiol
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Functional group containing one oxygen between two single bonded carbons
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ether
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Does alkene or alcohol numbering take priority?
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alcohol
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What would you call CH2=CH2CH-OH?
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2-propen-1-ol
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What would 6-bromo-4-hexen-2-ol look like?
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A chain 6 carbons long, with an OH attached at point 2, a double bond at point 4, and a Br at point 6
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What would CH3-CH2-CH=CH-SH be called?
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4-buten-1-thiol
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What would o-phenylphenol look like?
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A benzene ring with OH at 1 and a another benzene ring attached at 2
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What would you call a benzene ring with an OH attached at 1, and Cl attached at 2 and 5?
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2,5-dichlorophenol
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What is unique about naming simple ethers?
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SIMPLE ethers don't use IUPAC, they use common names. Complex ethers do use IUPAC.
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What would you call CH3-CH2-O-CH3?
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ethyl methyl ether or methoxyethane
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What would methyl phenyl ether look like?
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an O atom sandwiched between a benzene ring and a methyl group
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How do you name simple ethers (those with identical alkyls attached)?
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List the name of each alkyl or aromatic group attached to the O in alphabetical order, followed by the word ether
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What do you call CH3-O-CH3?
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Dimethyl ether
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How do you name complex ethers?
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Replace the suffix of the smaller alkyl with -oxy and then append that as a prefix to the larger alkyl name. Now number the main chain beginning at the end nearest the alkoxy group and give the location of the alkoxy group on the main chain.
e.g., CH3-O-CH2-Ch2-CH3 = 1-methoxypropane |
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What is the IUPAC and common name for a compound with an O atom sandwiched between a benzene ring and an ethyl group?
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Common: ethyl phenyl ether
IUPAC: ethoxybenzene |
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What would you call a compound with O sandwiched between an ethyl and a benzene ring?
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ethoxybenzene (ethyl phenyl ether)
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True or false: isomers of a given formula all fall into the same functional group.
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False. e.g., C2H6O = CH3-CH2-OH (ethyl alcohol) = CH3-O-CH3 (dimethyl ether)
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When do you call something an "iso" in the common name?
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When it is branched. E.g, CH3-CH2-CH2-OH is just propyl alcohol; CH3-CH-CH3 with OH coming off the middle C is isopropyl alcohol.
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Define heterocyclic compound
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rings with one or more atoms that are not carbon
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What do you call cyclic compounds with one or more atoms that aren't carbon?
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heterocyclic compounds
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Do cyclic ethers usually use IUPAC or common names, or both?
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common
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Which types of ethers usually use common names?
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Cyclic and simple ethers
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How are cyclic ethers numbered?
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Starting from the oxygen atom
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What suffix is used for cyclic ethers with 5 atoms?
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furan. e.g., 3-methylfuran
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What do you call a 5-atom ring with O instead of C at 1, and CH2-CH3 at 2?
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2-ethylfuran
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What do you call a 5-atom ring with O instead of carbon at one of the atoms, and no substituents?
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furan
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What do you call an unsaturated ether ring of six atoms?
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pyran
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Define furan
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a 5-atom cyclic ether
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What is a pyran?
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a 6-atom cyclic ether with one O atom
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What do you call a ring of six atoms with two C atoms replaced by O?
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dioxane
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What are dioxanes?
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6-atom rings with two C atoms replaced by O
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What do you call a 6 atom ring with O replacing C at points 1 and 3?
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1,3-dioxane
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What would 1,4-dioxane look like?
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A 6-atom ring with O replacing C atoms at points 1 and 4 in the ring
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What are dioxins?
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dioxanes bonded to aromatic rings
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What is the difference between furan and pyran?
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Furans are 5 atom rings with one O atom, pyrans are 6 atom rings with one O atom
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What is a hydrogen bond?
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A hydrogen bond is the attractive force between an H atom (as part of a compound) and a dipole negatively charged atom of a different compound. Usually the electronegative atom is oxygen, nitrogen, or fluorine.
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What three electronegative atoms are most common in hydrogen bonds?
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O, N and F
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Hydrogen bonding lowers or raises boiling temperatures?
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raises
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What kinds of compounds commonly form hydrogen bonds?
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ethers and alochols
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True or false: Alcohols are usually soluble in water
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True. The polar OH group hydrogen bonds with water, making alcohols with one to four carbon atoms very soluble in water.
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What makes the difference between soluble and insoluble alcohols?
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Alcohols with 5 or more C atoms do not hydrogen bond, so are insoluble in water.
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Are ethers or alcohols more soluble in water?
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Alcohols
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Why are phenols soluble in water?
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The hydroxyl (OH) group ionizes slightly as a weak acid, creating H3O and a phenol with an O- attached.
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What would a phenoxide ion look like?
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A benzene ring with O- having replaced one of the H+, giving the compound an ionic charge
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Do alcohol or ether molecules have higher boiling points? Why?
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Alcohols have higher boiling points because ethers do not bond to eachother like alcohols do, requiring more energy to separate them.
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What happens during the dehydration of an alcohol?
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an H and OH are removed from adjacent carbon atoms to produce water, a double bond forms between those carbon atoms producing an alkene.
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What do you call the process of H and OH being removed from alcohols to form water and an alkene?
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dehydration
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What does Saytzeff's Rule say?
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the major product of the dehydration of a secondary alcohol is the one that results when the H is removed from the C atom with the fewest H atoms. This occurs because the H of a secondary C atom is easier to remove than an H from a primary carbon atom.
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What two outcomes can result from the dehydration of a secondary alcohol?
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This could result in a double bond between the the C atom adjacent to the OH-bonded C with the fewest C bonds (major product) or a double bond between the OH-bonded C and one with more C bonds (minor product)
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What is the name of the compound produced by the dehydration of cyclobutanol?
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cyclobutene
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What process turns alcohols into alkenes?
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dehydration
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What is the name of an alcohol that forms 2-methylpropene through dehydration?
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2-methyl-2-propenol or 2-methyl-1-propanol
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How do ethers form?
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when two alcohol molecules dehydrate at low temperatures in the presence of an acid catalyst (e.g., H+). H is removed from one, and OH from the other and the remaining molecules join with one O sandwiched in the middle.
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If you add H+ and heat to two CH3-OH molecules, what is likely to result?
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The formation of an ether (CH3-O-CH3) through dehydration and H2O
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What happens in oxidation?
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There is an increase in bonds between O and C, either through gaining an O, or losing H (resulting in a double bond C=O)
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What happens in a reduction reaction?
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Some bonds between O and C break, reducing the number of O-C bonds either by completely losing the O or by gaining H.
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A loss of O from a C chain would be called what?
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reduction
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The addition of an O atom to a C chain would be called what?
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oxidation
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The oxidation of a primary alcohol creates what?
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an aldehyde (C bonded to at least one H and double bonded to O)
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How are aldehydes created?
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through the oxidation of primary alcohols, removing two H atoms, one from the OH group and another from the C bonded to the OH
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How do you name aldehydes?
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Replace the suffix with "al"
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The suffix "al" is used for what type of compound?
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Aldehydes
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What does oxidation of aldehydes turn them into?
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carboxylic acids
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Carboxylic acids are created how?
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through the oxidation of aldehydes
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How are carboxylic acids named?
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By replacing the suffix with "-oic acid"
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The suffix "-oic acid" is used for what?
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carboxylic acids
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The oxidation of a secondary alcohol results in what?
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a ketone
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How are ketones created?
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through the oxidation of secondary alcohols
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What happens in the oxidation of secondary alcohols to create ketones?
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One H atom is removed fro the OH and another from the C bonded to the OH group. The result is a ketone with the C=O double bond and C on both sides of the bonded C.
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How do you name ketones?
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By replacing the "e" suffix with "one"
e.g., Propenone, butanone, etc |
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Hexan-3-one is what type of compound?
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A ketone
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True or false: tertiary alcohols readily oxidize.
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False
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Thiols that undergo oxidation create...
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disulfides
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Disulfides result from the oxidation of what?
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Thiols
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What happens in the oxidation of thiols?
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Two thiols and an oxidizing compound react to create H2O through the loss of an H from each thiol, and the thiols then merge to form a disulfide
e.g., CH3-SH + CH3-SH ->[O] -> CH3-S2-CH3 + H2O |
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Combustion of alcohols produces what two compounds?
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CO2 and H2O
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What is the difference between an aldehyde and a ketone?
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In an aldehyde, the carbonly group is bonded to at least one hydrogen; in ketone, the carbonyl group is bonded to two C atoms
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What two types of molecules have carbonyl groups?
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Aldehydes and ketones
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What is the aldehyde of benzene called?
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benzaldehyde
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What is benzaldehyde?
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A benzene ring with a CHO attached (aldehyde because it's attached also to the C on the benzene)
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What would the name be of a carbon chain of 4 with a double bond to O and single bond to H at one end, and a CH3 bonded to the 3rd C?
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3-methylbutanal. It's an aldehyde so al ending. Aldehydes always occur at the end so no need to number the butanal part.
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What is another name for propanone?
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ketone
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What is another name for ketone?
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propanone
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What feature gives aldehydes and ketones higher boiling points?
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the polar carbonyl group
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Aldehydes and ketones have boiling points that are higher or lower than alcohols? Why?
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Lower. Though they have polar carbonyl groups, they do have not have H attached to the O so can not form hydrogen bonds with eachother.
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Arrange the following in order of lowest to highest boiling points:
aldehydes, ketones, alcohol, alkanes, |
alkanes, aldehydes/ketones, alcohol
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What group has the "al" suffix?
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aldehydes
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Why are aldehydes and ketones often soluble in water?
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carbonyl compounds with one to four C are very soluble in water
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Solubility of carbonyl compounds increases as....
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the length of the chain decreases
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Would ethanol have a higher or lower boiling point than ethanal? Why?
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Ethanol would have a higher boiling point because its molecules can hydrogen bond with each other.
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Why is acetone soluble in water?
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It is a ketone with a polar carbonyl group that bonds with the H atoms of H2O.
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Similar compounds with higher molar mass have higher boiling points. T or F
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True.
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Describe the process of reduction
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The addition of a catalyst such as Ni and H2 are added to an aldehyde or ketone and the H attach to the O and the C bonded to the O.
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What is the structure of formaldehyde?
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an aldehyde with the C bonded to an additional H.
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What would you call an aldehyde bonded to a second H atom?
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formaldehyde
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What do you call the hydrate of formaldehyde?
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formalin
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Explain the formation of carbonyl hydrates.
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In the presence of an acid or base, water breaks up and donates OH to the carbonyl carbon, while H bonds to the negative O.
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What is acetaldehyde?
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an aldehyde attached to CH3 (methyl)
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What do you call the compound of methyl attached to an aldehyde?
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acetaldehyde
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What do you call the compound of Cl3C attached to an aldehyde?
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chloral
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What is the hydrate of the compound of Cl3C attached to an aldehyde?
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chloral hydrate
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What is the structure of chloral?
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Cl3C attached to an aldehyde
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What is the hydrate of formaldehyde called and what is its structure?
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Formalin. C connected to two H atoms, and two OH groups.
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How are acetals formed?
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They form through the reaction of aldehydes or ketones with alcohols in the presence of an acid catalyst. The two H that were attached to the OH go to a spare O to form H2O in additio to the acetal
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What is created the the reaction of aldehydes or ketones with alcohols in the presence of an acid catalyst?
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An acetal
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What is the primary characteristic of acetals?
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two -OR groups are attached to a C atom. R represents any alkyl.
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What type of compound has two -OR groups attached to a C atom? R represents an alkyl.
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Acetal
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What is the intermediate structure formed during the creation of acetals called?
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hemiacetal
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What are hemiacetals?
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intermediate forms of acetals, formed when one of the two alcohol molecules adds to the carbonyl C
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What is propionaldehyde?
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A 3 carbon aldehyde
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What do you call an aldehyde with a 3 carbon chain?
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propionaldehyde
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When do cyclic hemiacetals form?
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when the carbonyl group and the OH group are in the SAME molecule
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How do you form a cyclic hemiacetal?
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Alcoholic aldehyde + acid = the chain loops around and connects to itself.
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How do cyclic acetals form?
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Alochols add to cyclic hemiacetals in the presence of an acid, which are formed when the OH and C=O are on the same molecule.
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Define structural isomer
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molecules with same molecular formula, but different bonding sequence
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Define stereoisomer
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identical formulas, but aren't structural isomers. They are bonded in the same sequence, but differ in how they're arranged in space
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Define chiral
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when stereoisomers have mirror images that are NOT superimposable
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When stereoisomers are superimposable, they are said to be...
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achiral
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When stereoisomers are NOT superimposable, they are said to be...
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chiral
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Define achiral
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When stereoisomers have mirror images that are superimposable
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Define enantiomer
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Stereoisomers that are mirror images that CANNOT be superimposed on each other.
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True or false: enantiomers are achiral.
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False. Enantiomers are NOT superimposable and so are chiral.
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What is a chiral carbon?
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a carbon atom attached to four unique atoms or groups of atoms, making it nonsuperimposable (chiral).
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What must be true for a C atom to be superimposable?
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It must be bonded to four atoms or groups of atoms (no double bonds) and at least two of the atoms or groups of atoms must be the same
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How do you draw a fischer projection?
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Horizontal and vertical lines represent bonds that point toward you and away, respectively. The chiral carbon is at the center. The most highly oxidized Carbon goes at the top.
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What letter is used as a prefix to the names of chiral molecules with OH on the right of the C?
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D
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What letter is used as a prefix to the names of chiral molecules with OH on the left of the C?
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L
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