Organic Chemistry

Learning Objectives

Organic Chemistry: Learning Guide 1 1. State the definition of organic chemistry. (p194) study of compounds that contain carbon and hydrogen 2. Why does carbon have a tendency to form so many different compounds? Because it is small and has 4 valance electrons 3. How many bonds can each carbon atom form? 4 4. (A) What type of bonding exists between atoms within molecules of organic compounds? covalent (B) This type of bonding produces properties such as high vapor pressure and low boiling point. What does this tell you about the intermolecular forces of attraction between organic molecules? IMFs are relatively weak in organic molecules

Organic Chemistry: Learning Guide 1 5. Explain why oil and water don’t mix, but table sugar(sucrose) and water do. (both oil and table sugar are organic molecules) (p71) ”Like dissolves Like” : oil is nonpolar, water is polar : sugar is polar, water is polar 6. Explain why salt solutions (NaCl (aq) ) conduct electricity, but sugar solutions (C 6 H 12 O 6(aq) ) do not. (p111) because salts are electrolytes, having ionic bonds and will dissociate in water – forming charged particles that will conduct electricity. Sugar is a covalent molecule that does not break apart in water 7. Explain why reactions between organic compounds are usually slower than those between inorganic compounds (p206) because organic molecules tend to be large and complex – it takes more energy and time to break bonds and form new ones

Organic Chemistry: Learning Guide 1 8. A structural formula shows the arrangement of each atom and the bond type in a compound 9. A structural isomer is a different form of a compound, having the same number of each element and bond type – just put together differently (isomers have the same molecular formulas, different names)

Organic Chemistry: Learning Guide 1

p p. 200p )19.)2.) 20.)3.) 21.)4.) 22.)5.) 23.)6.)

Organic Chemistry: Learning Guide 2 1.) Define hydrocarbon. (P.195-6) contain only H & C 2.) Explain why C 20 H 24 melts at 36 o C, but C 8 H 18 has a melting point of -56 o C. (relationship between #C atoms & MP)(p.196) more C needs more E to break up, so higher MP 3.) Provide four examples of hydrocarbons that are common fuels. NameMolecular FormulaCommon Use

Organic Chemistry: Learning Guide 2 4.) What is the difference between saturated & unsaturated compounds? (p.195) Saturated has Single bonds b / w C, Unsaturated has double & triple bonds b / t C 5.) Define homologous series. Group of compounds that change by the same unit - see table Q

Organic Chemistry: Learning Guide 2 Name\Prope rty Bond Type between C atoms General formula 2 carbon example: Name 2 carbon example: Structural Formula ALKANE ALKENE ALKYNE 6.) Complete the following table showing the 3 most important homologous series of hydrocarbons. (ref tables, p.196)

Organic Chemistry: Learning Guide 2 7.) Draw the complete structural formula for a straight-chain hydrocarbon containing 4 carbon atoms. (p.196) 8.) Draw the complete structural formula for a branched-chain hydrocarbon containing 4 carbon atoms. (p.196)

Organic Chemistry: Learning Guide 2 9.) Identify each of the following as (a) saturated or unsaturated and (b) alkane, alkene, alkane H H-C-C-H H l H-C=C-H H H H H-C-C-C-H H H-C-H H 1.a.2a.3a. 1b.2b.3b. H H l l H-C-C-H l l H-C-C-H l l H H H H l l H C=C-C=C H H-C=C-H 4a.5a.6a. 4b.5b.6b.

Organic Chemistry: Learning Guide ) Write the molecular formulas for the first 4 members of the homologous series: alkane. Methane ___________ Ethane_____________ Propane ___________ Butane_____________ 11.) Answer the following problems from the review book, page 198.

Flowchart for naming hydrocarbons Identify longest chain of carbons (determine prefix from # of carbons) Table P identify bond type (determine suffix from bond type) TableQ all single bonds one double bond one triple bond two double bonds alkane alkene alkyne alkadiene any HC branches? NOYES Done!!Count from side closest to branch & name alkyl group based on # of C present

Organic Chemistry: Learning Guide 3: Alkanes

Skill Practice: Alkanes 2,2,4 -trimethyl nonane 3-ethyl, 2,3-,dimethyl, hexane 2,2- dibromo, 3-methyl, heptane n-propane 1-chloro, 2-methyl butane2,4,6-trimethyl, 4-propyl, octane

Skill Practice: Alkanes

Organic Chemistry: Learning Guide 4: Alkenes & Alkynes 1.) Describe the kind of bonding found in an unsaturated compound. Double or triple bonds b / t C ’ s 2.) What is the general formula of an alkene? C n H 2 n

Parent ChainIUPAC Name Structural Formula Condensed Formula Molecular Formula 2 carbons C2H4 C2H4 3 carbons -C=C-C- 4 carbons 2-butene 5 carbons CH 3 CH 2 CHCHCH 3 6 carbons 3-hexene 6 carbons CH 3 CHCHCH 2 CH 2 CH 3 4.) Which of the above alkenes have isomers?

Organic Chemistry: Learning Guide 4: Alkenes & Alkynes 5.) How many bonds must each Carbon make with other atoms? 4 6.) Alkynes always contain one Triple bond ( C = C ) bond and their IUPAC name must end in - __yne______. 7.) What is the common name of ethyne? (p. 197) acetylene 8.) Determine the IUPAC name for the following : -C-C-C=C-C-

Skill Practice: Alkanes, Alkenes, Alkynes

Organic Chemistry: Learning Guide 5: Substitution, addition & Combustion Rxns S ubstitution Addition

Polymerization AdditionCondensation

Combustion IncompleteComplete

Organic Chemistry: Learning Guide 6: functional Groups Functional Group:

Organic Chemistry: Learning Guide 7: Alcohols 1.The functional group that gives alcohols their characteristic properties is the _hydroxyl_ group and its symbol is _OH___. 2. The IUPAC name for an alcohol ends in _”ol”_.

3. Draw the structural formula and write the IUPAC name for each of the following alcohols: 1 carbon alcohol __________________ 2 carbon alcohol ___________________ 4. Draw the structural formula for the following alcohols: 2- butanol3-methyl-3-pentanol

H H H | | | H  C  C  C  OH | | | H H H H H H | | | H  C  C  C  H | | | H OH H H | H  C  H H H | | H  C  C  C  H | | | H OH H 5. Monohydroxy alcohols are classified according to the number of carbon atoms that are bonded to the carbon atom with the  OH group. Primary alcohol Secondary alcohol Tertiary alcohol C atom with the  OH group C atom with the  OH groupC atom with the  OH group is bonded to 1 other C atom is bonded to 2 other C atoms is bonded to 3 other C atoms

7. A monohydroxy alcohol has ONE _OH_ per molecule. 8. A dihydroxy alcohol has __2 OH___ per molecule, but never more than one per carbon. 9. A trihydroxy alcohol has ____3 OH_____________ per molecule, but never more than one per carbon.

C 2 H 4 (OH) 2 Common name: IUPAC name: Use: Structure:

C 3 H 5 (OH) 3 Common name: IUPAC name: Use: Structure:

12. Describe the difference between ethanol (C 2 H 5 OH) and potassium hydroxide (KOH) in terms of the type of bonding. 13. Which of the following will conduct electricity? NaOH(aq), CH 3 OH(aq), C 6 H 12 O 6 (aq)

Write the balanced equation for the fermentation of glucose

Organic Chemistry: Learning Guide 8: Ethers R 1 -O-R 2 Ethers differ from alcohols because the “O” is in the interior of the Carbon Backbone, and and alcohol has the “OH” at the end of the carbons

Methyl Ethyl Ether

Name the molecules below: (a) H H H H (b) CH 3 CH 2 − O − CH 2 CH 3 | | | | H − C − O − C − C − C − | | | | H H H H _____________________

Organic Chemistry: Learning Guide 9: Adlehydes & Ketones

methanal Common name: Use: Structure:

Name of Aldehyde Condensed Structural Formula (circle functional group) CH 3 CHO propanal CH 3 CH 2 CH 2 CH 2 CHO

Name of Ketone Condensed Structural Formula (circle functional group) propanone _________________ (common name) CH 3 COCH 3 2-butanone

Organic Chemistry: Learning Guide 10: Organic Acids & Esters 1. Organic acids contain a carboxyl group: − COOH. Draw its structural formula. 2.To name an organic acid, drop the final “e” from the alkane name and add the ending ________and the word “acid”. A 5 carbon organic acid would be called ____________________.

Name Structural Formula Molecular Formula methanoic acid (formic acid) HCOOH ethanoic acid __________________ _ (common name) 2 formulas: C 2 H 5 COOH

O | | O | | R  C  O  R’ 5. Esters contain the functional group  C  O  within a carbon chain. The general formula can be written as where R and R ’ may represent different carbon chains. Draw the structural formula for an ester molecule that has a 3-carbon chain as R and a 2-carbon chain as R ’. Circle the functional group. R – C- O R ’ 6. Esters are formed in the process called _________________________________.

H O | | | H  C  C  OH | H H | HO  C  H | H H O H | | | | H  C  C  O  C  H + H 2 O | | H H The reaction for the formation of an ester: carboxylic acid + primary alcohol  ester + wa ter + → ethanoic acid methanolmethyl ethanoate

Naming esters Locate the COO, draw a line to separate: R acid -COO-R alcohol Alcohol: remove the “-anol” replace with “-yl” Acid: replace the “-ic” with “-oate”

Draw the structural formulas for reaction that produces methyl hexanoate:

Esterfication Alcohol + Acid  Ester + Water CH 3 CH 2 OH + C 3 H 7 COOH  C 3 H 7 COOCH 2 CH 3 + H 2 O ethanol + butanoic acid -> ethyl butanoate + water

Organic Chemistry: Learning Guide 11: Amines & Amides 1. Amines contain the functional group ___________. 2. Write the general formula for an amine. Circle the functional group.

Organic Chemistry: Learning Guide 11: Amines & Amides 1. Amides contain the functional group ___________. 2. Write the general formula for an amide. Circle the functional group.

5. Explain the system for naming amines and amides.

Organic Chemistry: Learning Guide 12: Amino Acids & polymerization Amino acid molecules contain two functional groups. Circle and label the functional groups on the amino acid molecule below. 2. Amino acids are the building blocks of _PROTEIN__ molecules.

3. What is a polymer? a long repeating chain of the same monomer 4. Name three natural polymers. Name three synthetic polymers. DNAnylon RNApolyester proteinspolystyrene 5. Amino acid molecules are linked together by the removal of a H 2 O molecule. This process is called dehydration synthesis or condensation polymerization.

6. Indicate (by circling) the location from which the water molecule is removed when the two amino acids below are linked together. Draw the products of the reaction. Circle the amide linkage on the organic product.

An addition polymerization reaction involves the joining of monomers of an unsaturated compound by breaking the C=C double bonds. 8. Draw the structural formulas for the addition polymerization reaction that forms polyethylene: nC 2 H 2  (C 2 H 2 ) n -C=C-  … -C-C-C-C-…. 1 MONOMER 1 MONOMER

Organic Chemistry: Learning Guide 13: Lipid Molecules & Saponification Lipid (fat) molecules are composed of one glycerol and three fatty acid molecules. 1.Glycerol is classified as a trihydroxy alcohol because it contains three hydroxyl groups. Long chain organic acid molecules found in lipids are called fatty acidmolecules.

#2 #3

4. The products of a saponification reaction are soap and glycerol. Describe the process of saponification. #5

Organic Chemistry: Learning Guide 14: Organic Reactions Directions: Classify each of the following organic reactions using the key provided. (A) Fermentation(B) Esterfication(C) Saponification (D) Polymerization(E ) Addition(F) Substitution (G) Hydrogenation(H) Oxidation (Complete Combustion) (I) Oxidation (Incomplete Combustion)

1 C 2 H 4 + H 2  C 2 H CH 4 + Br 2  CH 3 Br + HBr HCOOH + CH 3 OH  HCOOCH 3 + HOH zymase C 6 H 12 O  2 C 2 H 5 OH + 2CO 2 5 HCOOH + CH 3 (CH 2 ) 3 OH  HCOO(CH 2 ) 3 CH 3 + H C 2 H 4 + H 2  C 2 H 6

7 C 3 H 5 (C 17 H 35 COO) 3 + 3NaOH  3C 17 H 35 COONa + C 3 H 5 (OH) 3 8 n C 2 H 4  (-C 2 H 4 -)n 9 RCOOH + R’OH  RCOOR’ + H 2 O 10 CH 4 + 2O 2  CO 2 + 2H 2 O 11 2CH 4 + 3O 2  2CO + 4H 2 O 12 CH 4 + O 2  C + H 2 0

13 C 5 H 10 + H 2  C 5 H C 3 H 8 + Cl 2  C 3 H 7 Cl + HCl 15 C 3 H 8 + 2Cl 2  C 3 H 6 Cl + 2HCl 16 H H H H CH 3 C=CCH 3 +Cl 2  CH 3 C-CCH 3 Cl Cl 17 CH 3 OH + C 2 H 5 COOH  C 2 H 5 COOCH 3 + H 2 O

Funky Groups 1 1.)