organic chemistry packet -...

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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…)

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Page 1: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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…)

Page 2: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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.

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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

Page 4: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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

Page 5: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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!

Page 6: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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

Page 7: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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)

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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:

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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

Page 10: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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)

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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

Page 12: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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

Page 13: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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)

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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?

Page 15: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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)

Page 16: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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.

Page 17: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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)

Page 18: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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

Page 19: Organic Chemistry Packet - hallsciencedsa.weebly.comhallsciencedsa.weebly.com/.../6/8/7/56874993/organic_chemistry_pac… · Organic Chemistry Packet Basic Organic Chemistry Organic

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)

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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.