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88 Cards in this Set
- Front
- Back
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alcohol
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a compound that has an -OH group bonded to a saturated, alkane-like carbon atom (R-OH)
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phenol
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a compound that has an -OH group bonded directly to an aromatic, benzene like ring (Ar-OH)
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ether
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a compound that has an oxygen atom bonded to two organic groups, R-O-R
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the high boiling point of water is due to....
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hydrogen bonding
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what bonds form between alcohol (or phenol) molecules
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hydrogen bonds
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methyl alcohol
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(methanol) CH3OH- known as wood alcohol
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how is methyl alcohol made
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by reaction of carbon monoxide with hydrogen
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what is methanol (methyl alcohol) used for
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industrially as a solvent, and as a starting material for preparing formaldehyde
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properties of methyl aclohol (methanol)
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colorless, miscible (soluble) with water and toxic. causes blindness in low doeses and death in larger amounts
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ethyl alcohol
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(ethanol) CH3CH2OH- known as grain alcohol and is present in alcoholic beverages
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industrially, ethyl alcohol is made by...
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hydration of ethylene
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isopropyl alcohol
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(CH3)2CHOH- often called rubbing alcohol
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what is isopropyl alcohol used for
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rubdowns and in atringents, as a solvent, a sterilant and as a skin cleanser
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ethylene glycol and its properties
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HOCH2CH2OH- it is a diol. it is a colorless liquid, miscible with water, and insoluble in nonpolar solvents. it is highly toxic and has a slightly sweet taste
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what is ethylene glycol used for
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an engine antifreeze and coolant, also used as a starting material for the manufacture of polyester
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glycerol and its properties
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HOCH2CH(OH)CH2OH- it is a triol, also called glycerin. it is a colorless liquid that is miscible with water, nontoxic and has a sweet taste that is useful in foods
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because of glycerol's extensive hydrogen bonding, it is an extremely _______ fluid
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viscous
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step one in naming alcohols
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name the parent compound- find the longest chain with the hydroxyl substituent attached, and name chain by replacing the -e ending of the corresponding alkane with -ol
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dialcohols (diols)
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has two hydroxy (-OH) groups
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thriol
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has 3 -OH groups
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step 2 in naming alcohols
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number the carbon atoms in the main chain- begin at end nearer hydroxyl group, ignoring other substituents
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when naming unsaturated alcohols, the double bond is shown by the infix _____ and the hydroxyl group is shown by the suffix _____
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-en-, -ol
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step 3 in naming alcohols
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write the name, placing the number that locates the hydroxyl group immediately before the compound name. number all other substituents and list them alphabetically.
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when naming a diol....
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attach the ending diol to the alkane name, add the 2 numbers indicating the carbons bonded to the OH groups
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glycols
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a dialcohol or diol with the 2 -OH groups on adjacent carbons
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alcohols are classified as primary, secondary, or tertiary according to.....
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the number of carbon substituents bonded to the hydroxyl-bearing carbon
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primary alcohol
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(1°)- 1 substituent (one R group on OH bearing carbon)
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secondary alcohol
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(2°)- 2 substituents (2 R groups on OH bearing carbon)
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tertiary alcohol
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(3°)- 3 substituents ( 3 R groups on OH bearing carbon)
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alcohols are nonpolar or polar? because of what
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polar because of the electronegative oxygen atom
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_________ bonding occurs in alcohols and has a strong influence on....
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hydrogen bonding, on alcohol properties
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straight-chain alcohols with up to 12 carbons are....
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liquid
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methanol and ethanol are ________ with water and can dissolve small parts of......
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miscible, ionic compounds. both are also miscible with many organic solvents
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all alcohols are composed of what two parts
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a hydrophilic "water-loving" part and a hydrophobic "water-fearing" part
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hydrophilic
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water-loving
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hydrophobic
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water-fearing
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alcohols with a larger hydrophobic part are more like _____ and less like ______
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alkanes and less like water
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alcohols with two or more -OH groups can form more than one.....
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hydrogen bond
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because alcohols with 2 or more OH groups can form more than one hydrogen bond, they are.....
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higher boiling and more water-soluble than similar alcohols with one -OH group
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dehydration
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(elimation reaction) the loss of water from an alcohol- with the treatment of a strong acid- to yield an alkene
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how does dehydration occur
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reaction is driven to completion by heating, the -OH group is lost from one carbon and an -H is lost from an adjacent carbon to yield an alkene
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when more than one alkene can result from dehydration. a mixture of products is formed. the major product has the greater number of....
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alkyl groups directly attached to the double-bond carbons
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oxidation of alcohol
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occurs when primary and secondary alcohols are converted into carbonyl-containing compounds by an oxidizing agent
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carbonyl group
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a carbon attached to an oxygen by a double bond (C=O)
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an organic oxidation is
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one that increases the number of C-O bonds and/or decreases the number of C-H bonds
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an organic reduction is
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one that decreases the number of C-O bonds and/or increases the number of C-H bonds
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how does oxidation of alcohol occur
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2 hydrogen atoms are removed during reaction - one from the -OH group and one from the carbon attached to the -OH group.
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oxidation of primary alcohols converts them into
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aldehydes under controlled conditions or carboxylic acid if an excess of oxidant is used
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oxidation of secondary alcohols (R2CHOH) converts them into
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ketones (R2C=O) on treatment with oxidizing agents
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______ alcohols do not normally react with oxidizing agents because.....
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tertiary alcohols, because they do not have a hydrogen on the carbon atom to which the -OH group is bonded
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potassium dichromate oxidation of ethanol to acetic acid is the basis for....
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alcohol breathing test used by law enforcement agencies
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the alcohol breath test is based on the different in color between the....
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dichromate ion (reddish orange) and chromium (III) ion (green)
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the word phenol is the name both of a _______ as well as a ________
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specific compound (hydroxybenzene C6H5OH) and a family of compounds
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phenol is a medical antiseptic that....
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numbs the skin
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other alkyl-substituted phenols such as cresols are common as....
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disinfectants
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phenols are usually named with the ending _____ rather than ______
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phenol, rather than benzene
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the properties of phenols are influenced by the...
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electronegative oxygen and hydrogen bonding
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properties of phenols
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most are somewhat water-soluble and have higher melting and boiling points than similar alkylbenzenes, they are less soluble in water than alcohols.
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alcohols and phenols are very weakly acidic because of the...
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positively-polarized -OH hydrogen
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alcohols and phenols _____ slightly in solution and establish _____ between _________________
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dissociate, equilibria between neutral and anionic forms
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methanol and ethanol dissociate so little in water that their aqueous solutions are...
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neutral (pH 7)
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alkoxide ion
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the anion resulting from deprotonation of an alcohol, RO⁻. it is as strong a base as a hydroxide ion
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how is an alkoxide ion produced
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by reaction of an alkali metal with an alcohol
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how is a phenoxide ion produced
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by reaction of a phenol with dilute aqueous sodium hydroxide
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ethers
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compounds with two organic groups bonded to the same oxygen atom
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how are ethers named
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by identifying the two organic groups and adding the word ether
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cyclic ethers are often referred to by their
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common names
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alkoxy group
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an -OR group
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ethers do not form ______ bonds to one another
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hydrogen
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ethers are ______ boiling than alkanes but ____ boiling than alcohols
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higher, lower
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ethers are _____-like in many properties and do not react with.....
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alkane-like, acids or bases
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simple ethers are highly________
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flammable
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ethers must be handled with care and stored in the absence of......
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oxygen
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thiols
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also called mercaptans, are sulfur analogs of alcohols- contains an -SH group (R-SH)
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the systematic name of a thiol is formed by...
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adding -thiol to the parent hydrocarbon name
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thiols have an appalling....
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odor
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skunk scent and the odor when garlic and onions are being sliced are...
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thiols
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natural gas is odorless, but methanethiol is added to....
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make leak detection easy
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thiols react with mild oxidizing agents to yield....
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disulfides
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disulfide
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a compound that contains a sulfur-sulfur bond (RS-SR)
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how are disulfides produced
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two thiols join together in a reaction, the hydrogen from each is lost, and a bond forms between the sulfurs
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thiols are important because they occur in the....
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amino acid cysteine, which is part of many proteins
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the proteins in hair are unusually rich in ______ and ______ groups
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S-S and S-H groups
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the simplest halogen-containing compounds are....
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alkyl halides, RX
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alkyl halide
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a compound that has an alkyl group bonded to a halogen atom, R-X
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alkyl halide common names consist of the name of the ______ followed by the halogen name with an _____ ending
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alkyl group, -ide ending
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in alkyl halides, the halogen atom is a _______ on a parent alkane
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substituent
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halogenated compounds are used widely in industry as....
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solvents and degreasing agents
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