Goals for the day…Review practice Exam 3Review naming and physical properties of

carboxylic acids and esters.Review physical properties of carboxylic acids

and esters.Review reactions of carboxylic acids and esters.Review lipids (both fatty acid lipids and steroids).Review physical properties of lipids.Review reactions of lipids.

Now a bit of a review…

Write the IUPAC name for each of the structures below in your notebook…

O

HO

F O

O

Answers…

3-fluoro heptanoic acid isopropyl hexanoate

O

HO

F O

O

Draw structures from the following names in your notebook…

Butanoic acid methyl pentanoate

Answers (something like this)…

Butanoic acid methyl pentanoate

O

HO

O

O

Which of the following are water soluble?

H

O

OH

O

O

O

O OH

NH2

Answer…

Most groups with O or N with 5 or fewer carbons are water soluble.

Groups with just carbons and hydrogens (and ethers) are not water soluble.

H

O

OH

O

O

O

O OH

NH2

Rank the following in order of decreasing melting point in your notebook, then we’ll check together…

_____>______>______>______>______>______

H

O

OH

OOOHNH2

a b c d e f

Ranked highest to lowest…(hydrogen bonding > dipole > van deer Waals)

__b___>__d____>__c____>___a___>__e____>__f_

H

O

OH

OOOHNH2

a b c d e f

Reactions (try these in your notebook)…

OH

O NaOH

OH

O CH3OH

H+

Answers…

OH

O NaOH

OH

O CH3OH

H+

O

O

O

O

CH3

Reactions (try these in your notebook)…

O

O NaOH

H2O

H+O

O

Answers…

O

O NaOH

H2O

H+O

O

O

O

+HO

OH

O

+HO

Lipids

Five types of fatty acid lipids:

Waxes triglycerides

glycerophospholipids prostoglandins

Steroids:

O

O

O

O

O

P

O

OO

NH2

OHHN

O

O

R

P

O O

O

N

sphingomyein

Types of Fatty Acid Lipids

Learning Check

Assign the melting point (mp) of −17°C, 13°C, or 69°C to each one of the following 18-carbon fatty acids, and list the fatty acids in order from highest to lowest melting point. Explain.

A. oleic acid

B. stearic acid

C. linoleic acid

Solution Stearic acid is saturated and would have a higher melting point than the unsaturated fatty acids. Oleic acid, which has one double bond, has a higher mp than linoleic acid, which has two double bonds.

B. stearic acid mp 69°C saturatedA. oleic acid mp 13°C unsaturated with one

double bond C. linoleic acid mp −17°C unsaturated with two

double bonds

Which of these are: saturated,

monounsaturated omega-3 and monounsaturated omega-6?

A. CH3—CH2—CH2—CH2—CH2—CH2—CH2—CH2—CH2—COOH

B.

C.

Solution

A. saturated (no double bonds)CH3—CH2—CH2—CH2—CH2—CH2—CH2—CH2—CH2—COOH

B. monounsaturated omega-3 (double bond at 3)

C. monounsaturated omega-6 (double bond at 6)

Recognize the difference…Oil: at room temperature, it is a

viscous liquid. Triacylglyceride that has unsaturation, so has a low melting point.

Fat: at room temperature, it is a solid. Triacylclyceride that is saturated, so has a higher melting point.

Wax: Contains an ester of a “fat” and an alcohol.

Glycerophospholipids Contain Amino Alcohols.

Three amino alcohols found in glycerophospholipids are choline, serine, and ethanolamine.

In the body, at a physiological pH of 7.4, these amino alcohols are ionized.

Insert structures of amino alcohols pg 618 bottom

Four ReactionsThe chemical reactions of triacylglycerols are similar to

those of alkenes and esters.

esterification (making the triacylglycerol)ester hydrolysis (breaking the triacylglycerol into the

fatty acid and glycerol)Saponification (adding NaOH and making a salt)hydrogenation (adding H2 to the double bonds)

Esterifcation…To form the triacylglycerols, you take 3 fatty

acids and glycerol…ester formation…

HydrolysisIn acid or enzyme hydrolysis, water adds to the ester bonds.triacylglycerols hydrolyze forming glycerol and

three fatty acids.a strong acid, such as HCl or H2SO4, or an

enzyme catalyst is required.

Saponificationglycerol + salts of fatty acids (soap)

Fat or oil + strong base

Hydrogenation of Glyceryl Trioleate

In a hydrogenation reaction, H2 adds across the double bond to form a carbon–carbon single bond.

Learning CheckDraw (explain) the condensed structural formula of the product of the following

reaction.

O

O

CH2

O

O

CH

CH2 O

O

C

C

C

(CH2)7 CH CH

CHCH(CH2)7

CHCH(CH2)7

(CH2)5 CH3

(CH2)5 CH3

(CH2)5 CH3

+ 3H2

Ni

Solution

CH2 (CH2)14

CH2

CH O C

O

O C

O

O

O

C

(CH2)14 CH3

(CH2)14 CH3

CH3

Multiple Choice (for your review).

1. The –COOH group is called a(n) _______.

carboxyl groupcarbonyl groupaldehyde grouphydroxyl group

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1. The –COOH group is called a(n) _______.

carboxyl groupcarbonyl groupaldehyde grouphydroxyl group

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2. The carboxylic acid responsible for the pain of an ant sting is _______.

ethanoic acidmethanoic acidbutanoic acidpropanoic acid

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2. The carboxylic acid responsible for the pain of an ant sting is _______.

ethanoic acidmethanoic acidbutanoic acidpropanoic acid

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3. Which is the acid found in vinegar?

nitric acidacetic acidvaleric acidformic acid

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3. Which is the acid found in vinegar?

nitric acidacetic acidvaleric acidformic acid

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4. The IUPAC name and the common name for the following carboxylic acid are _______. O CH3-C-OH

ethanoic acid; acetic acidmethanoic acid; formic acidethanoic acid; formic acidmethanoic acid; acetic acid

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4. The IUPAC name and the common name for the following carboxylic acid are _______. O CH3-C-OH

ethanoic acid; acetic acidmethanoic acid; formic acidethanoic acid; formic acidmethanoic acid; acetic acid

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5. Which acid is palmitic acid?

CH3(CH2)12COOH

CH3(CH2)10COOH

CH3(CH2)14COOH

CH3(CH2)16COOH

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5. Which acid is palmitic acid?

CH3(CH2)12COOH

CH3(CH2)10COOH

CH3(CH2)14COOH

CH3(CH2)16COOH

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6. Glacial acetic acid is _______.

a frozen solution of acetic acida mixture of acetic acid and water pure acetic acidacetic acid mixed with a base

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6. Glacial acetic acid is _______.

a frozen solution of acetic acida mixture of acetic acid and water pure acetic acidacetic acid mixed with a base

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7. The IUPAC name and the common name for the following ester are _______. O CH3-O-C-CH3

methyl ethanoate; methyl formatemethyl methanoate; methyl acetatemethyl ethanoate; methyl acetatemethyl methanoate; methyl formate

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7. The IUPAC name and the common name for the following ester are _______. O CH3-O-C-CH3

methyl ethanoate; methyl formatemethyl methanoate; methyl acetatemethyl ethanoate; methyl acetatemethyl methanoate; methyl formate

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8. The ester responsible for the flavor and odor of a banana is _______.

ethyl benzoatepentyl butanoateoctyl ethanoatepentyl ethanoate

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8. The ester responsible for the flavor and odor of a banana is _______.

ethyl benzoatepentyl butanoateoctyl ethanoatepentyl ethanoate

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9. Ethyl acetate is _______.

C2H5COOCH3

CH3COOC2H5

CH3COOCH3

C2H5COOC2H5

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9. Ethyl acetate is _______.

C2H5COOCH3

CH3COOC2H5

CH3COOCH3

C2H5COOC2H5

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10.What two types of chemicals are mixed to form an ester?

a carboxylic acid and a basea carboxylic acid and an alcohola base and an alcoholtwo different carboxylic acids

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10.What two types of chemicals are mixed to form an ester?

a carboxylic acid and a basea carboxylic acid and an alcohola base and an alcoholtwo different carboxylic acids

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11.Reactions that produce esters also produce _______.

H2O

H2

H3O+

O2

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11.Reactions that produce esters also produce _______.

H2O

H2

H3O+

O2

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12.Dacron is a synthetic fiber representative of which type of compound?

carboxylic acidesterpolyesteralcohol

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12.Dacron is a synthetic fiber representative of which type of compound?

carboxylic acidesterpolyesteralcohol

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13.The ester that provides the main ingredient for products like Bengay and Icy Hot is _______.

acetylsalicylic acidmethyl salicylateoxaloacetic acidethyl butyrate

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13.The ester that provides the main ingredient for products like Bengay and Icy Hot is _______.

acetylsalicylic acidmethyl salicylateoxaloacetic acidethyl butyrate

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14.Which of the following compounds is not soluble in water?

CH3CH2CH2CH2CH3

Ob) CH3CH2CO–Na+

Oc) CH3COCH3

Od) CH3CH2COH

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14.Which of the following compounds is not soluble in water?

CH3CH2CH2CH2CH3

Ob) CH3CH2CO–Na+

Oc) CH3COCH3

Od) CH3CH2COH

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15.Alkaline hydrolysis of large, fatty esters is called _______.

solvationsaponificationsublimationhydration

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15.Alkaline hydrolysis of large, fatty esters is called _______.

solvationsaponificationsublimationhydration

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