Organic Chemistry

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63 Terms

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steps for naming alkanes

1. name the **main chain** (the longest continuous chain of carbons)
2. **number** the carbon atoms in the main chain
* start at the end closest to the first substituent
3. identify and number the **branching substituent**
4. write the name as a single word
* use hyphens to separate different prefixes and commas to separate numbers
* list substituents in alphabetical order
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properties of alkanes
* called **paraffins** since they don’t react as most chemicals
* will burn in a flame producing carbon dioxide, water, and heat
* react with Cl2 in the presence of light to replace H’s with Cl’s
* boiling points and melting points increase as size of alkane increases
* forces between molecules are weak
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cracking
large alkane + hydrogen gas → smaller alkane
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reforming
small alkane → larger alkane + hydrogen gas
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halogenation (substituation)
replace H with a halogen atom

* initiated by addition of energy in the form of heat or ultraviolet light
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combustion
hydrocarbon + oxygen → carbon dioxide + water

* all hydrocarbons undergo combustion
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steps for naming cycloalkanes
* count the number of carbon atoms in the ring and the number in the largest substituent chain
* if the number of carbon atoms in the ring is equal or greater than the number in the substituent the compound is named as an alkyl-substituted cycloalkane
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isomers
different molecules with the same molecular formula
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structural isomers
different pattern of atom attachment
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alkene
contain a double bond (C=C)

* one double bond = CnH2n
* have straight chains and are unsaturated
* polyunsaturated = many double bonds
* much more reactive than alkanes
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naming alkenes

1. find the longest continuous carbon chain containing the **double bond**
2. identity the substituents
3. number the chain from the end **closest** to the **double bond**
4. write the name in the following order:
* substituents in alphabetical order
* number of first carbon **double bond**
* name of main chain
* end with **-ene**
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alkynes
contain a triple bond

* one triple bond = CnH2n-2
* have straight chains and are unsaturated
* more reactive than alkenes
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naming alkynes

1. find the longest continuous carbon chain that contains the **triple bond**
2. identify the substituents
3. number the chain from the end **closest** to the **triple bond**
4. write the name in the following order:
* substituents in alphabetical order
* number of first carbon **triple bond**
* name of main chain
* end with **-yne**
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gemoetric isomerism
result of rotations around the double bond being highly restricted
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cis isomerism
groups are bonded on the **same** side
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trans isomerism
groups are bonded on opposite sides
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aromatic hydrocarbons
contain a ring structure with a series of alternating single and double bonds in a **delocalized** arrangement

* in simple aromatic compounds, the **benzene ring** is the parent chain
* if the attached benzene group is not easily named the benzene ring is the attached branch, called the **phenyl** group
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numbering carbons on the benzene ring
* 1,2 - ortho (o)
* 1,3 - meta (m)
* 1,4 - para (p)
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addition reaction
adding a molecule across the multiple bond (for alkenes and alkynes)
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substitution reaction
the hydrogen atoms in an alkane may be substituted by a halogen such as F2, Cl2, Br2
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hydrogenation
adding H2

* converts unsaturated molecule → saturated
* alkene/alkyne + H2 → alkane
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halogenation
adding X2 where X = F, Cl, Br, I
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hydrohalogenation
adding HX where HX is polar

* when adding a polar reagent to a double or triple bond the positive part attaches to the carbon with the most H’s
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hydration (hydrocarbons)
adding water

* converts unsaturated hydrocarbon → alcohol
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Markovnikov’s rule
in the addition of HX to alkene, the H attaches to the carbon with the most H’s, and the X attached to the end with the most alkyl substituents
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organic halides
a group of compounds commonly used as refigerants (CFC’s) and non-stick coating (Teflon)

* many organic halides are toxic and/or carcinogenic
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properties of organic halies
* the bonds between the **carbon** and **halogens** are more **polar** than those between **carbon** and **hydrogen**
* **alkyl halides** are **more polar** than their hydrocarbon parents
* they are more **soluble** in **polar solvents** than their hydrocarbon parents and have **higher boiling points**
* when a compound such as **propane** reacts with a **halogen** a mixture of compounds containing 1,2,3 or more **halogens** form
* the more **halogenated** a compound is the more polar it is
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preparing organic halides
* **alkenes** and **alkynes** readily add halogens or hydrogen halides to their double or triple bonds
* **Markovnikov’s rule** applies when hydrogen halides are reactants
* alkene/alkyne + hydrogen halide → organic halide
* compounds with **benzene rings** have a substitution reaction
* **elimination reaction**: a hydroxide ion is used to eliminate a hydrogen and halide ion from adjacent carbon atoms to form a double bond making an **alkene**
* alkane + OH → alkene + water + halogen
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alcohol
a water molecule with one of the hydrogen atoms replaced with an alkyl group (R - O - H)
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classifications of alcohol

1. **primary alcohols**: hydroxide is attached to an alkyl group attached to **one** other alkyl group
2. **secondary alcohols**: hydroxide is attached to an alkyl group attached to **two** other alkyl groups
3. **tertiary alcohols**: hydroxide is attached to an alkyl group attached to **three** other alkyl groups
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properties of alcohols
* much **higher boiling points** than parent alkanes
* more **soluble** than parent alkanes
* properties are due to H-bonding among molecules
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hydration (alcohols)
reacting alkenes with water in the presence of a catalyst results in an alcohol

* alkene + water → alcohol
* OH is found on the second carbon due to **Markovnikov’s rule**
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ether
a water molecule with both of the hydrogen atoms replaced with alkyl groups (R - O - R) or (R - O - R’)
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properties of ethers
* don’t form hydrogen bonds since they lack an OH group
* more **polar** than hydrocarbons because of the **dipole** arising from their C-O-C bonds
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naming ethers
add **oxy** to the prefix of the **smaller** hydrocarbon group and **join** it to the name of the **larger** hydrocarbon group
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preparing ethers
condensation: ethers are formed by the reaction of **2 alcohols** and the **elimination** of a **water molecule**

* alcohol + alcohol → ether + water
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aldehydes
consist of an **alkyl** group bonded to a **carbonyl** group with a **hydrogen** atom on the end
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ketones
consist of **two alkyl** groups attached to a **central carbonyl** group
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naming aldehydes and ketons
* **aldehyde**: name ends with **-al**
* **ketones**: name ends with **-one**
* if the carbon chain has 5 or more carbon atoms a number is needed to indicate the location of the carbonyl group
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properties of aldehydes and ketones
* **lower boiling points** and **less soluble** than corresponding alcohols
* **more soluble** than corresponding alkanes
* aldehydes and ketones can mix with both **polar** and **non-polar** substances
* allows **non-polar** materials to be mixed with **polar materials**
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preparing aldehydes and ketones from alcohols by oxidation reaction
* when **primary alcohol** is oxidized, an H atom remained on the C atom and an aldehyde is produced
* primary alcohol + (O) → aldehyde + water
* when **secondary alcohol** is oxidized, the carbonyl group that forms is attached to two alkyl groups forming a ketone
* secondary alcohol + (O) → ketone + water
* **tertiary alcohols** don’t react since there’s no hydrogen available for oxidation
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hydration (aldehydes and ketones)
* hydrogen can be added to the carbonyl group in aldehydes and ketones
* high temperatures and catalysts are required for this reaction
* this is the reverse of the controlled oxidation of alcohols
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carboxylic acids
characterized by the presence of carboxyl functional groups (R-COOH)
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naming carboxylic acids
* the carboxyl group is made up of a **hydroxyl** (OH) bound to the C atom on a carbonyl group
* the main chain is the longest chain containing the **carboxyl group**
* ends with **-oic acid**
* when naming multiple carboxyl groups the suffix **-dioic** is used
* when more than two carboxyl groups are present, all COOH groups may be named as substituents on the parent chain
* the parent chain doesn’t include the carboxylic atoms
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properties of carboxylic acids
* highly **polar** molecules
* the **polarity** of the carboxyl group makes carboxylic acids **soluble** in water
* chains longer than **ten carbons** insoluble in water
* **higher boiling points** than their corresponding alkanes
* **smaller** members are soluble in water, **larger** carboxylic acids are relatively **insoluble**
* **conduct** electricity
* react with organic bases in neutralization reactions
* **short chain** carboxylic acids are **liquids** at standard temperature
* **long chain** carboxylic acids are **waxy solids**
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preparing carboxylic acids
* when **alcohol** is **mildy oxidized**, an **aldehyde** is produced


* if this aldehyde is oxidized further a **carboxylic acid** is produced
* alcohol + (O) → aldehyde
* aldehyde + (O) → carboxylic acid
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ester
similar to carboxylic acids but th eH atom in the acid is replaced with another alkyl group (R - COO - R)
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naming esters
* the name of an ester has 2 parts
* first part: the name of the alkyl group used in the esterification process
* second part: the name of the acid
* the ending of the acid name change from -oic acid to -oate
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properties of esters
* the presence of the **carbonyl group** make esters somewhat **polar**
* esters are **less polar** than corresponding carboxylic acids because they lack an OH group capable of H bonding
* they are **less soluble** in water with **lower melting and boiling points** than corresponding alcohols and carboxylic acids
* **smaller esters** are **liquid** at standard temperatures while **longer esters** are **insoluble**
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esterification
* carboxylic acid + alcohol → ester + water
* alcohol acts as an organic base and carboxylic acid acts as an acid
* the ester formed is considered an organic salt
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hydrolysis
* reverses esterification by reacting the ester with an acid or base
* ester + acid/base → acid + alcohol
* a bond is broken by the addition of water resulting in two or more products
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amines
ammonia with one to all of its hydrogens substituted by alkyl groups
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classifications of amines

1. primary amine: one hydrogen is substituted with an alkyl group
* prepared by reacting ammonia with an alkyl halide
* ammonia + alkyl halide → primary amine + hydrogen halide
2. secondary amine: two hydrogens are substituted with alkyl groups
* prepared by reacting a primary amine further with an alkyl halide
* primary amine + alkyl halide → secondary amine + alkyl halide
3. tertiary amine: all three hydrogens are substituted with alkyl groups
* prepared by reacting a secondary amine further with an alkyl halide
* secondary amine + alkyl halide → tertiary amine + alkyl halide
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naming amines
* amines are nitrogen derivatives of an **alkane**
* amines can also be named as **alkyl derivatives** of ammonia
* **diamines**: molecules with 2 amino groups
* for secondary and tertiary amines include the N-prefix to show the substituted groups on the amine
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properties of amines
* primary and secondary amines are **very polar** due to the N-H bond which allows them to H-bond with each other
* tertiary amines don’t have N-H bonds and can’t H-bond
* **higher boiling** and **melting points** than similar sized ethers and alkanes
* smaller amines are **soluble** in water
* N-C and N-H bonds are **more polar**
* amines share a **lower boiling point** than alcohols of similar size because N-H bonds are less polar than O-H bonds
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amide
hydrocarbon that contains a carbonyl group bonded to a nitrogen atom

* similar to esters but the N atom replaces the O atom in the chain of an ester
* they are the backbone of all protein molecules
* in proteins amide bonds are called **peptides**
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properties of amides
* amides have a **polar** carbonyl group and amides with a least one NH group can form strong hydrogen bonds among themselves
* **higher boiling points**that their corresponding hydrocarbon derivatives
* **weak bases** that are **insoluble** in water
* **low molecular weight** amides are **slightly soluble**
* can be **hydrolyzed** in acidic or basic conditions to produce a carboxylic acid and an amine
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naming amides
* the first part of an amide’s name comes from the amine
* the second part of the name comes from the acid
* ends with the suffix **-amide**
* if one or more alkyl groups is attached to the N atom the upper case N is used to clarify the location
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preparing amides
* **condensation**: carboxylic acids react with **ammonia** or **primary** or **secondary** amines to produce amides
* carboxylic acid + ammonia → amide + water
* tertiary amines don’t undergo condensation reactions since they lack the extra H atoms needed to make water
* amides can also be made with **primary amines** and **carboxylic acids** by **condensation** reactions
* carboxylic acid + primary amine → amide + water
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polymer
made up of a group of **monomers** (usually 10 or more)

* **monomer**: a hydrocarbon derived molecule
* polymers may contain thousands of individual monomers, the subscript ***n*** is used to indicate the number of repeating units
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addition polymerization
consists of three stages (initiation, propagation, and termination)

* an **initiating molecule** with an **unpaired electron** forms a bond with one of the **carbon**atoms in the **double bonded monomer**
* this yields an unpaired electron on the other end of the monomer
* this electron can then form **covalen bonds** with another group
* the reaction continues/propigates
* the chain grows until **two unpaired electrons combine** forming a **covalent bond** that **links** the growing chains together
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cross-linking
occurs between -dienes because the second **double bond** allows for the formation of **covalent bonds** between different chains of monomers
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condensation polymers
when monomers join end to end in ester or amide linkages they form **polyesters** and **polyamides**