Goals for the day… Review practice Exam 3 Review naming and 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…

Answers… 3-fluoro heptanoic acid isopropyl hexanoate

Draw structures from the following names in your notebook… Butanoic acidmethyl pentanoate

Answers (something like this)… Butanoic acidmethyl pentanoate

Which of the following are water soluble?

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.

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

Ranked highest to lowest… (hydrogen bonding > dipole > van deer Waals) __b___>__d____>__c____>___a___>__e____>__f_

Reactions (try these in your notebook)…

Answers…

Reactions (try these in your notebook)…

Answers…

Lipids

Five types of fatty acid lipids: Waxes triglycerides glycerophospholipids prostoglandins Steroids: 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°Csaturated A. 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. CH 3 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —COOH B. C.

Solution A. saturated (no double bonds) CH 3 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —COOH B. monounsaturated omega-3 (double bond at 3) C. monounsat urated 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

Know properties of Cholesterol… is the most important and abundant steroid in the body. is a sterol because it contains an oxygen atom as a hydroxyl group, –OH on carbon 3. has a double bond between carbon 5 and carbon 6. has methyl –CH 3 groups, at carbon 10 and 13. has a carbon chain at carbon 17.

Know properties of bile salts… are synthesized from cholesterol in the liver. are stored in the gallbladder and secreted into the small intestine. have a polar and a nonpolar region. help in the absorption of cholesterol into the intestinal mucosa.

Know the types of lipoproteins…

Know types of lipid structures… Lipoproteincell membrane

Four Reactions The 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…

Forming triacylglycerides (esterification)… Glycerol has 3 OH groups, so does 3 esterification reactions!

Forming triacylglycerides (esterification)… The product is a triacylglyceride was formed from 3 fatty acids and glycerol (highlighted in yellow)…

Hydrolysis In 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 H 2 SO 4, or an enzyme catalyst is required.

Another view of hydrolysis… Remember, it is the reverse reaction. The triglyceride reacts with water to form glycerol and 3 fatty acids…

Saponification glycerol + salts of fatty acids (soap) Fat or oil + strong base

Another view of saponification… A triacylglyceride reacts with 3 molecules of NaOH to form glycerol and 3 molecules of soap.

Hydrogenation of Glyceryl Trioleate In a hydrogenation reaction, H 2 adds across the double bond to form a carbon–carbon single bond.

Hydrogenation… How many molecules of H2 will react with this triglyceride? Hint on the next slide…

Hydrogenation… Remember to count the number of double bonds in the fatty acid chains…

Hydrogenation… There are 3 double bonds in the red chain, none in the blue, and 1 in the green, so 4 molecules of H2 will react! …

Cis vs. Trans Fats In vegetable oils, the unsaturated fats usually contain cis double bonds. during hydrogenation, some cis double bonds are converted to trans double bonds (more stable), causing a change in the fatty acid structure.

Type of lipid? What type of lipid is this?...

This is a steroid (testosterone to be specific!

Multiple Choice (for your review).

1.The –COOH group is called a(n) _______. carboxyl group carbonyl group aldehyde group hydroxyl group © 2013 Pearson Education, Inc.

1.The –COOH group is called a(n) _______. carboxyl group carbonyl group aldehyde group hydroxyl group © 2013 Pearson Education, Inc.

2.The carboxylic acid responsible for the pain of an ant sting is _______. ethanoic acid methanoic acid butanoic acid propanoic acid © 2013 Pearson Education, Inc.

2.The carboxylic acid responsible for the pain of an ant sting is _______. ethanoic acid methanoic acid butanoic acid propanoic acid © 2013 Pearson Education, Inc.

3.Which is the acid found in vinegar? nitric acid acetic acid valeric acid formic acid © 2013 Pearson Education, Inc.

3.Which is the acid found in vinegar? nitric acid acetic acid valeric acid formic acid © 2013 Pearson Education, Inc.

4.The IUPAC name and the common name for the following carboxylic acid are _______. ethanoic acid; acetic acid methanoic acid; formic acid ethanoic acid; formic acid methanoic acid; acetic acid © 2013 Pearson Education, Inc.

4.The IUPAC name and the common name for the following carboxylic acid are _______. ethanoic acid; acetic acid methanoic acid; formic acid ethanoic acid; formic acid methanoic acid; acetic acid © 2013 Pearson Education, Inc.

5.Which acid is palmitic acid? CH 3 (CH 2 ) 12 COOH CH 3 (CH 2 ) 10 COOH CH 3 (CH 2 ) 14 COOH CH 3 (CH 2 ) 16 COOH © 2013 Pearson Education, Inc.

CH 3 (CH 2 ) 12 COOH CH 3 (CH 2 ) 10 COOH CH 3 (CH 2 ) 14 COOH CH 3 (CH 2 ) 16 COOH © 2013 Pearson Education, Inc. 5.Which acid is palmitic acid?

6.Glacial acetic acid is _______. a frozen solution of acetic acid a mixture of acetic acid and water pure acetic acid acetic acid mixed with a base © 2013 Pearson Education, Inc.

6.Glacial acetic acid is _______. a frozen solution of acetic acid a mixture of acetic acid and water pure acetic acid acetic acid mixed with a base © 2013 Pearson Education, Inc.

7.The IUPAC name and the common name for the following ester are _______. methyl ethanoate; methyl formate methyl methanoate; methyl acetate methyl ethanoate; methyl acetate methyl methanoate; methyl formate © 2013 Pearson Education, Inc.

7.The IUPAC name and the common name for the following ester are _______. methyl ethanoate; methyl formate methyl methanoate; methyl acetate methyl ethanoate; methyl acetate methyl methanoate; methyl formate © 2013 Pearson Education, Inc.

8.The ester responsible for the flavor and odor of a banana is _______. ethyl benzoate pentyl butanoate octyl ethanoate pentyl ethanoate © 2013 Pearson Education, Inc.

8.The ester responsible for the flavor and odor of a banana is _______. ethyl benzoate pentyl butanoate octyl ethanoate pentyl ethanoate © 2013 Pearson Education, Inc.

9.Ethyl acetate is _______. C 2 H 5 COOCH 3 CH 3 COOC 2 H 5 CH 3 COOCH 3 C 2 H 5 COOC 2 H 5 © 2013 Pearson Education, Inc.

9.Ethyl acetate is _______. C 2 H 5 COOCH 3 CH 3 COOC 2 H 5 CH 3 COOCH 3 C 2 H 5 COOC 2 H 5 © 2013 Pearson Education, Inc.

10.What two types of chemicals are mixed to form an ester? a carboxylic acid and a base a carboxylic acid and an alcohol a base and an alcohol two different carboxylic acids © 2013 Pearson Education, Inc.

10.What two types of chemicals are mixed to form an ester? a carboxylic acid and a base a carboxylic acid and an alcohol a base and an alcohol two different carboxylic acids © 2013 Pearson Education, Inc.

11.Reactions that produce esters also produce _______. H 2 O H 2 H 3 O + O 2 © 2013 Pearson Education, Inc.

11.Reactions that produce esters also produce _______. H 2 O H 2 H 3 O + O 2 © 2013 Pearson Education, Inc.

12.Dacron is a synthetic fiber representative of which type of compound? carboxylic acid ester polyester alcohol © 2013 Pearson Education, Inc.

12.Dacron is a synthetic fiber representative of which type of compound? carboxylic acid ester polyester alcohol © 2013 Pearson Education, Inc.

13.The ester that provides the main ingredient for products like Bengay and Icy Hot is _______. acetylsalicylic acid methyl salicylate oxaloacetic acid ethyl butyrate © 2013 Pearson Education, Inc.

13.The ester that provides the main ingredient for products like Bengay and Icy Hot is _______. acetylsalicylic acid methyl salicylate oxaloacetic acid ethyl butyrate © 2013 Pearson Education, Inc. Photo from yahoo.com/photos

14.Which of the following compounds is not soluble in water? CH 3 CH 2 CH 2 CH 2 CH 3 O b) CH 3 CH 2 CO – Na + O c) CH 3 COCH 3 O d) CH 3 CH 2 COH © 2013 Pearson Education, Inc.

14.Which of the following compounds is not soluble in water? CH 3 CH 2 CH 2 CH 2 CH 3 (this is an alkane) O b) CH 3 CH 2 CO – Na + O c) CH 3 COCH 3 O d) CH 3 CH 2 COH © 2013 Pearson Education, Inc.

15.Alkaline hydrolysis of large, fatty esters is called _______. solvation saponification sublimation hydration © 2013 Pearson Education, Inc.

15.Alkaline hydrolysis of large, fatty esters is called _______. solvation saponification sublimation hydration © 2013 Pearson Education, Inc.