Goals for the day… Review practice Exam 3 Review 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…

Answers… 3-fluoro heptanoic acid isopropyl hexanoate

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

Answers (something like this)… Butanoic acid methyl 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… _____>______>______>______>______>______

__b___>__d____>__c____>___a___>__e____>__f_ 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°C saturated 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? 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 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…

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 H2SO4, or an enzyme catalyst is required.

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

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

Learning Check Draw (explain) the condensed structural formula of the product of the following reaction.

Solution

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 _______. O CH3-C-OH 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 _______. O CH3-C-OH 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? CH3(CH2)12COOH CH3(CH2)10COOH CH3(CH2)14COOH CH3(CH2)16COOH © 2013 Pearson Education, Inc. 59

5. Which acid is palmitic acid? CH3(CH2)12COOH CH3(CH2)10COOH CH3(CH2)14COOH CH3(CH2)16COOH © 2013 Pearson Education, Inc. 60

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. 61

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. 62

7. The IUPAC name and the common name for the following ester are _______. O CH3-O-C-CH3 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 _______. O CH3-O-C-CH3 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 _______. C2H5COOCH3 CH3COOC2H5 CH3COOCH3 C2H5COOC2H5 © 2013 Pearson Education, Inc. 67

9. Ethyl acetate is _______. C2H5COOCH3 CH3COOC2H5 CH3COOCH3 C2H5COOC2H5 © 2013 Pearson Education, Inc. 68

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 _______. H2O H2 H3O+ O2 © 2013 Pearson Education, Inc.

11. Reactions that produce esters also produce _______. H2O H2 H3O+ O2 © 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. 73

12. Dacron is a synthetic fiber representative of which type of compound? carboxylic acid ester polyester alcohol © 2013 Pearson Education, Inc. 74

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.

14. Which of the following compounds is not soluble in water? CH3CH2CH2CH2CH3 O b) CH3CH2CO–Na+ c) CH3COCH3 d) CH3CH2COH © 2013 Pearson Education, Inc.

14. Which of the following compounds is not soluble in water? CH3CH2CH2CH2CH3 O b) CH3CH2CO–Na+ c) CH3COCH3 d) CH3CH2COH © 2013 Pearson Education, Inc.

15. Alkaline hydrolysis of large, fatty esters is called _______. solvation saponification sublimation hydration © 2013 Pearson Education, Inc. 79

15. Alkaline hydrolysis of large, fatty esters is called _______. solvation saponification sublimation hydration © 2013 Pearson Education, Inc. 80