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Name:______________________ Date:_____________Period:____
Organic Chemistry Packet
Basic Organic Chemistry
Organic chemistry centers on the chemistry of a few elements, mainly _________________, and
a few others:
For the most part (and at all times in this class), all atoms obey the Octet Rule. This means:
o Carbon forms _____ bonds and has _____ lone pairs.
o Nitrogen (and its family) forms _____ bonds and has _____ lone pair.
o Oxygen (and its family) forms _____ bonds and has _____ lone pairs.
o The halogens form _____ bond and have _____ lone pairs.
o Hydrogen forms _____ bond.
What elements will we completely ignore for the next few weeks?
Properties of Organic Compounds:
o __________________ - do not dissolve in water
o ________ melting points. Why?
Increases as ________________________ increases. Why?
o React ______________ than ionic compounds. Why?
Types of Compounds:
o ________________________ - all carbon atoms are attached by ________________ bonds
o ________________________ - at least one _______________ or ______________ bond is present
o
Line-Bond Structures
These are exactly like Lewis Dot Structures (except you leave out the lone pairs, for simplicity)
Draw the Line-Bond Structure for CH3CH2CH(CH3)CH2CH3 in the space below:
Who wants to do that again??? (Me either…)
Name:______________________ Date:_____________Period:____
Skeletal Structures
These structures are much cleaner, but at first it seems like many things are missing.
However, as with most chemistry, there are rules that help with this!
What do you notice about these two structures?
Rules for Drawing Structures:
o Carbons are represented by the __________ of a line or the ___________________ of two lines
How many carbons are in each of the following structures? Number them.
o Hydrogens that are attached to ______________ are _________ drawn.
How many hydrogens are in each of the following structures? Draw them in!
o All atoms _________________ carbon and hydrogen must be shown. Hydrogens attached to
these atoms must also be shown.
Name:______________________ Date:_____________Period:____
Practice:
o Draw the skeletal structure for the following molecules:
Write the formula for the following molecules. Draw the line-bond structure for the left
column.
CC
CC
C
C
C
H
H
H
H
H
HH
H
HH
HH
H
H
HH
CC
CC
C
C
C
C
CC
C
CC C
CBr
H
H
H
H
H
H H
H H
CC
CC
CC
Cl
C
H
HH
H
H
HH
H
H
HH
HH
OH O
OH O
OH O
Name:______________________ Date:_____________Period:____
Homework 1
Directions: Draw the skeletal structures for the following molecules.
1) CH3CH2CH3
2) CH3CH(CH3)CH(CH3)CH2CH2CH3
3) CH3CH2CH2CH(CH2CH3)CH2CHCHCH3
4) CH2O
5) CH3CH2CH2CH2COOH
6) BrC(CH3)COOH
7) CH3CH2CH2COOCH2CH3
8) CH3CH2CH2OCH2CH3
Name:______________________ Date:_____________Period:____
Organic Nomenclature (IUPAC – International Union of Pure & Applied Chemistry)
Hydrocarbons – compounds that are made of only _____________ and ___________________
Base Names:
Prefix Length of Carbon Chain
Meth
Eth
Prop
But
Pent
Hex
Hept
Oct
Non
Dec
Alkanes – simplest hydrocarbons
o Saturated (only _____________ bonds)
o General formula:
o What is the formula for an alkane with 5
carbons?
o What is the formula for an alkane with
20 carbons?
o Name the following alkanes:
CH4
C2H6
C3H8
C4H10
C8H18
Alkenes – unsaturated hydrocarbons with one ______________ bond
o General formula:
o What is the formula for an alkene with 8 carbons?
o What is the formula for an alkene with 43 carbons?
o Name the following alkenes:
C3H6
C5H10
C9H18
o Isomers – molecules with the same molecular formula but different structural formulas
1-pentene has the double bond between the 1st and 2nd carbon
2-pentene has the double bond between the 2nd and 3rd carbon
o Add all of the possible names to the alkenes listed above!
Name:______________________ Date:_____________Period:____
Alkynes – unsaturated hydrocarbons with one ______________ bond
o General formula:
o What is the formula for an alkyne with 7 carbons?
o What is the formula for an alkyne with 34 carbons?
o Name the following alkynes (all possible isomers):
C2H2
C5H8
C10H18
Alkyl Groups – branches that have one less hydrogen than the corresponding alkane
isopropyl sec-butyl tert-butyl isobutyl
o Write the formula AND draw the skeleton structures for the following alkyl groups:
Propyl—
Butyl—
Decyl—
Cycloalkanes – hydrocarbons with a ring structure
o General formula:
o Write the formula and draw the skeleton structure for the following cycloalkanes:
Cyclopropane (very uncommon)
Cyclobutane
Cyclopentane
Name:______________________ Date:_____________Period:____
Homework 2
Directions: Write the formula and draw the skeletal structures for the following hydrocarbons.
1) Cycloheptane
2) 3-octene
3) 1-decyne
4) Propene
5) 2-hexyne
6) 3-octen-1-yne
Directions: Name the following hydrocarbons using the IUPAC Rules.
1)
2)
3)
4)
5)
6)
7)
8)
Name:______________________ Date:_____________Period:____
Branched Hydrocarbon Nomenclature
Find the longest continuous chain of carbons. Note: This may not be straight!
o This is your _________________ chain.
Number the carbons in your parent chain so the branches are attached to the _______________
numbered carbons.
Add ______________ to the names of the groups to identify the carbon they are attached to.
o These numbers become _________________ to the parent chain.
Use prefixes to indicate any branches that appear more than once.
o Di – ______
o Tri – ______
o Tetra – ______
o Penta – ______
List the alkyl groups in ________________________ order.
Use punctuation:
o _______________ to separate numbers from each other
o _______________ to separate numbers with words
If a double or triple bond is present, start numbering closest to the double/triple bond!
Practice:
o Number and name the following branched hydrocarbons:
Name:______________________ Date:_____________Period:____
o Draw the skeleton structure for the following branched hydrocarbons:
3-ethyl hexane
2,2,4-trimethylpentane
2,3-dimethylhexane
5-ethyl-2-3-9-trimethyldecane
Methylcyclopentane
5-ethyl-2-octene
Name:______________________ Date:_____________Period:____
Homework 3
Directions: Draw the following skeletal structures.
1) 4-ethyloctane
2) 2-methylnonane
3) 3,3-dimethylpentane
4) 3-ethylpentane
5) 3-ethyl-2-methylheptane
6) 3-ethyl-4-(1-methylpropyl)-2,2-
dimethyloctane
Directions: Name the following branched hydrocarbons using IUPAC Rules.
1)
2)
3)
4)
5)
6)
7)
Name:______________________ Date:_____________Period:____
Alkyl Halides
Compounds that are formed when any ________________
replaces one or more hydrogens in a hydrocarbon.
Use a _______________ to specify where the halogen is
attached.
Practice:
o Name the following alkyl halides:
o Draw the skeleton structure for the following alkyl halides:
Bromocyclohexane
3-chloro-1-pentene 1-bromo-7-iodo-heptane
Alcohols
Compounds that are formed when a __________________ group (-OH) replaces one or more
hydrogens in a hydrocarbon.
o Primary alcohol – the OH group is attached to an ________ carbon
o Secondary alcohol – the OH group is attached to a ______________ carbon
o Tertiary alcohol – the OH group is attached to a ____________________________ carbon
Name:______________________ Date:_____________Period:____
To name alcohols, replace the final “e” with “ol”.
o Methane
o Ethane
o Propane
o Butane
o Pentane
Use a number to specify on which carbon the –OH group is attached (should be on the lowest
possible)
o Draw and name all possible structural isomers of pentanol. Why are there only 3?
Practice:
o Name the following alcohols:
o Draw the skeleton structure for the following alcohols and classify them as primary,
secondary, or tertiary:
2,2-propanediol
4-methyl-cyclohexanol
3-methyl-1,10-decanediol
3-ethyl-3-hexanol
tert-butanol
4-penten-2-ol
Name:______________________ Date:_____________Period:____
Homework 4
Directions: Draw the skeletal structures for the following molecules.
1) Ethanol
2) 2-chloropropane
3) Fluoromethane
4) Isobutanol
5) 3-chloro-cyclopentanol
6) 2-bromo-3-methyl-1-butanol
Directions: Name the following alkyl halides and alcohols using the IUPAC Rules.
1)
2)
3)
4)
5)
Name:______________________ Date:_____________Period:____
Carboxylic Acids
Compounds that are formed when a terminal H atom is replaced by a carboxyl group (-COOH)
To name carboxylic acids, replace the final “e” with “oic” acid
o Methane
o Ethane
o Propane
o Butane
o Pentane
Why does a carboxylic acid functional group have to be on the END of a hydrocarbon chain?
Aldehydes
Compounds that are formed when a terminal H atom is replaced by a –CHO group.
To name aldehydes, replace the final “e” with “al”.
o Methane
o Ethane
o Propane
o Butane
o Pentane
Why does an aldehyde have to be on the END of a hydrocarbon chain?
Name:______________________ Date:_____________Period:____
Homework 5
Directions: Draw the skeletal structures for the following molecules.
1) Hexanoic acid
2) Ethanal
3) 5-fluoropentanal
4) 2-methylbutanoic acid
5) 2-cyclohexyldecanal
6) 2,3,4-triethylnonanoic acid
Directions: Name the following carboxylic acids and aldehydes using the IUPAC Rules.
1)
2)
3)
4)
5)
6)
Name:______________________ Date:_____________Period:____
Ketones
Compounds that are formed when a C=O group is in the middle of a hydrocarbon chain.
To name ketones, replace the final “e” with “one”. Add a number to denote the carbon in the
C=O group
o Propane
o Butane
o Pentane
o Hexane
Why are methanone and ethanone not possible compounds?
Ethers
Compounds that are formed when an oxygen atom is bonded to two hydrocarbon chains.
To name ethers, name the two hydrocarbon chains as alkyl groups and then add ether. List the
shorter carbon branch first.
Name:______________________ Date:_____________Period:____
Homework 6
Directions: Draw the skeletal structures for the following molecules.
1) Isopropyl cyclohexyl ether
2) 1-fluoro-3-hexanone
3) Ethyl 2-methylpentyl ether
4) 3-decanone
5) 2,2-dimethyl-4-heptanone
6) Diisopropyl ether
Directions: Name the following ketones and ethers using the IUPAC Rules.
1)
2)
3)
4)
5)
6)
Name:______________________ Date:_____________Period:____
Esters
Compounds containing a –COO group in the middle of a hydrocarbon chain.
To name esters, name the alkyl chain AFTER the –COO group, then name the carbon chain
including the C=O carbon, replacing the final “e” with “oate”.
Amines
Compounds that are formed when a hydrogen atom is replaced by a nitrogen group (-NH2)
To name amines, replace the final “e” with “amine”
o Methane
o Ethane
o Propane
Amides
Compounds containing a –CONH2 group at the end of a hydrocarbon chain.
To name amides, replace the final “e” with “amide”
o Methane
o Ethane
o Propane
Name:______________________ Date:_____________Period:____
Homework 7
Directions: Draw the skeletal structures for the following molecules.
1) Isopropanamine
2) Ethyl pentanoate
3) Cyclopentanamine
4) 2-methylbutanamide
5) Isopropyl ethanoate
6) 4-chloropentanamide
Directions: Name the following esters, amines and amides using the IUPAC Rules.
1)
2)
3)
4)
5)
6)
Name:______________________ Date:_____________Period:____
Summary Sheet
Make yourself a summary of all the functional groups on the back of this page! This will be a quick
reference sheet for your final exam.
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