Review Two

Exam Setup… Naming/Drawing questions Multiple choice Short answer Reaction Page

Topics…

Alcohols, Phenols, Ethers, Thiols, Aldehydes, Ketones Topics (page 1)… Alcohols, Phenols, Ethers, Thiols, Aldehydes, Ketones Naming Physical properties (water solubility) Needs to have an oxygen or nitrogen to be water soluble * 5 carbons… (melting point/ boiling point ranking) Hydrogen bonding > dipole > van der Waals Reactions (on following slides)

Reactions…

Please try this in your notebook…just put what goes in the box! 

Two more to try…

Acetal; hemiacetal; carbohydrates Topics (page 2)… Acetal; hemiacetal; carbohydrates Recognizing the hemiacetal/acetal carbon in sugars Recognize the structures of ribose, fructose, glucose, and galactose. Recognize the structures of maltose, sucrose, and lactose. Recognize the structures of amylose, amylopectin, cellulose, and glycogen Answer questions relating to the relationships of alpha & beta glycosidic linkages between these sugars…

Are these alpha or beta?

Both are beta…b/c the OH groups are up!

These are the four sugars you need to know…

Disaccharides… Recognize the structures of maltose, sucrose, and lactose.

Which sugar gives galactose and glucose upon hydrolysis? B) maltose C) sucrose D) tetraose

Which sugar gives galactose and glucose upon hydrolysis? B) maltose C) sucrose D) tetraose

Which is sucrose? b a c

Sucrose is “c” remember that it is the one that has fructose in it, so has the 5 membered ring. What are the other two sugars?.. b a c

The other two sugars are… A (maltose…2 glucoses) B (lactose…galactose & glucose) C (sucrose…glucose & fructose)

Recognize the structures of amylose, amylopectin, cellulose, and glycogen

Which is amylopectin? a b c

Amylopectin is the polysaccharide with the branches…what are the other two?... B (amylopectin) c

A (amylase…alpha chain of glucoses) B (amylopectin) C (cellulose…beta chain of glucoses)

Multiple Choice Questions…

The name of the functional group of aldehydes and ketones is a(n)_______. double bond hydroxyl group carbonyl group carboxyl group

The name of the functional group of aldehydes and ketones is a(n)_______. double bond hydroxyl group carbonyl group carboxyl group

2. The IUPAC name for the following compound is_______. Br O CH3CHCH2CH 3-bromobutanal 2-bromobutanal 3-bromobutanone 2-bromobutanone

2. The IUPAC name for the following compound is_______. Br O CH3CHCH2CH 3-bromobutanal 2-bromobutanal 3-bromobutanone 2-bromobutanone

3. The common name for the following compound is_______. O CH3CH methyl aldehyde methyl ketone formaldehyde acetaldehyde

3. The common name for the following compound is_______. O CH3CH methyl aldehyde methyl ketone formaldehyde acetaldehyde

4. The compound CH3COCH3 is_______. a) formic acid b) formaldehyde c) acetone d) methanone 55

4. The compound CH3COCH3 is_______. a) formic acid b) formaldehyde c) acetone d) methanone 56

5. The condensed structural formula of the 5. The condensed structural formula of the alcohol needed to give 2-butanone is_______. CH3CH2CHCH3 CH3CH2CH2CH2OH CH3CH2CH2OH CH3CHCH3 OH

5. The condensed structural formula of the 5. The condensed structural formula of the alcohol needed to give 2-butanone is_______. CH3CH2CHCH3 CH3CH2CH2CH2OH CH3CH2CH2OH CH3CHCH3 OH

The IUPAC name for the following compound is______. Cl CH3CH2CCH2CHCH3 2-chloro-4-hexanone 2-chloro-4-hexanal 5-chloro-3-hexanone 5-chloro-3-hexanal

The IUPAC name for the following compound is______. Cl CH3CH2CCH2CHCH3 2-chloro-4-hexanone 2-chloro-4-hexanal 5-chloro-3-hexanone 5-chloro-3-hexanal

7. The structural formula of the organic product when hydrogen and a nickel catalyst reduce the following is_______. O CH3CCH3 CH3CH2OH OH CH3CHCH3 CH3CH2CH2OH CH3OH

7. The structural formula of the organic product when hydrogen and a nickel catalyst reduce the following is_______. O CH3CCH3 CH3CH2OH OH CH3CHCH3 CH3CH2CH2OH CH3OH

9. When an aldehyde is oxidized, the product is a(n)_______. a) alcohol b) aldehyde c) ketone d) carboxylic acid

9. When an aldehyde is oxidized, the product is a(n)_______. a) alcohol b) aldehyde c) ketone d) carboxylic acid

10. Ketones are prepared by the oxidation of_______. a) primary alcohols b) secondary alcohols c) tertiary alcohols d) carboxylic acids

10. Ketones are prepared by the oxidation of_______. a) primary alcohols b) secondary alcohols c) tertiary alcohols d) carboxylic acids

13. Isopropanol could be made from the reduction of which compound? a) propionic acid b) ethyl methyl ketone c) acetone d) acetaldehyde 67

13. Isopropanol could be made from the reduction of which compound? a) propionic acid b) ethyl methyl ketone c) acetone d) acetaldehyde 68

14. Most biologically active enantiomers consist of_______. a) D-enantiomers b) L-enantiomers c) only one enantiomer d) both enantiomers

14. Most biologically active enantiomers consist of_______. a) D-enantiomers b) L-enantiomers c) only one enantiomer d) both enantiomers

15. Chiral molecules are optically active_______. a) always b) under most conditions c) under some conditions d) never 71

15. Chiral molecules are optically active_______. a) always b) under most conditions c) under some conditions d) never 72

alcohol ether phenol thiol 2. The presence of a hydroxyl group attached directly to a benzene ring makes the compound a(n)_______. alcohol ether phenol thiol © 2013 Pearson Education, Inc. 73

2. The presence of a hydroxyl group attached directly to a benzene ring makes the compound a(n)_______. alcohol ether phenol thiol © 2013 Pearson Education, Inc. 74

3. The IUPAC name for the following compound is_______. CH3OCH2CH3 methyl ethyl ether methoxyethane ethyl methyl ether ethoxymethane © 2013 Pearson Education, Inc.

3. The IUPAC name for the following compound is_______. CH3OCH2CH3 methyl ethyl ether methoxyethane ethyl methyl ether (note this is correct alphabetically)!  ethoxymethane © 2013 Pearson Education, Inc.

4. The formula for anesthetic “ether” is_______. CH3OCH3 C2H5OH C2H5OC2H5 CH3OC2H5 © 2013 Pearson Education, Inc. 77

4. The formula for anesthetic “ether” is_______. CH3OCH3 C2H5OH C2H5OC2H5 CH3OC2H5 © 2013 Pearson Education, Inc. 78

6. Which alcohol is least soluble in water? CH3OH C3H7OH C6H13OH C10H21OH © 2013 Pearson Education, Inc. 79

6. Which alcohol is least soluble in water 6. Which alcohol is least soluble in water? (note: this is the one with the most carbons) CH3OH C3H7OH C6H13OH C10H21OH © 2013 Pearson Education, Inc. 80

8. All except which of the following compounds are soluble in water? ethanol 2-propanol dimethyl ether 1-hexanol © 2013 Pearson Education, Inc.

8. All except which of the following compounds are soluble in water? ethanol 2-propanol dimethyl ether 1-hexanol © 2013 Pearson Education, Inc.

9. The alcohol present in alcoholic beverages is_______. methyl alcohol ethyl alcohol isopropanol denatured alcohol © 2013 Pearson Education, Inc.

9. The alcohol present in alcoholic beverages is_______. methyl alcohol ethyl alcohol isopropanol denatured alcohol © 2013 Pearson Education, Inc.

alcohols are ionic compounds they have higher molecular weight 10. Alcohols boil at appreciably higher temperatures than hydrocarbons of similar formula weight because_______. alcohols are ionic compounds they have higher molecular weight alcohols interact through hydrogen bonding alcohols are soluble in water © 2013 Pearson Education, Inc.

alcohols are ionic compounds they have higher molecular weight 10. Alcohols boil at appreciably higher temperatures than hydrocarbons of similar formula weight because_______. alcohols are ionic compounds they have higher molecular weight alcohols interact through hydrogen bonding alcohols are soluble in water © 2013 Pearson Education, Inc.

11. Secondary alcohols undergo oxidation to form_______. aldehydes ketones carboxylic acids secondary alcohols to not undergo oxidation © 2013 Pearson Education, Inc.

11. Secondary alcohols undergo oxidation to form_______. aldehydes ketones carboxylic acids secondary alcohols to not undergo oxidation © 2013 Pearson Education, Inc.

12. The dehydration of an alcohol produces a(n)_______. ether aldehyde alkene carboxylic acid © 2013 Pearson Education, Inc.

12. The dehydration of an alcohol produces a(n)_______. ether aldehyde alkene carboxylic acid © 2013 Pearson Education, Inc.

hexane < diethyl ether < butanol 13. Which grouping gives the proper order for increasing solubility in water? (most soluble is on the right side)… hexane < diethyl ether < butanol diethyl ether < butanol < hexane butanol < hexane < diethyl ether hexane < butanol < diethyl ether © 2013 Pearson Education, Inc.

hexane < diethyl ether < butanol 13. Which grouping gives the proper order for increasing solubility in water? hexane < diethyl ether < butanol diethyl ether < butanol < hexane butanol < hexane < diethyl ether hexane < butanol < diethyl ether © 2013 Pearson Education, Inc.

15. Chiral molecules are optically active_______. a) always b) under most conditions c) under some conditions d) never 93

15. Chiral molecules are optically active_______. a) always b) under most conditions c) under some conditions d) never 94

1. The following monosaccharides are all aldoses except_______. fructose ribose xylose galactose © 2013 Pearson Education, Inc.

1. The following monosaccharides are all aldoses except_______. fructose ribose xylose galactose © 2013 Pearson Education, Inc.

2. The monosaccharide that is also called blood sugar is_______. ribulose galactose glucose ribose © 2013 Pearson Education, Inc.

2. The monosaccharide that is also called blood sugar is_______. ribulose galactose glucose ribose © 2013 Pearson Education, Inc.

3. Ribose is a(n)_______. aldotetrose aldopentose ketotriose ketohexose © 2013 Pearson Education, Inc.

3. Ribose is a(n)_______. aldotetrose aldopentose ketotriose ketohexose © 2013 Pearson Education, Inc.

4. Which is not a reducing sugar? fructose glucose maltose sucrose © 2013 Pearson Education, Inc. 101

fructose glucose maltose sucrose 4. Which is not a reducing sugar? (this is because it is a disaccharide) fructose glucose maltose sucrose © 2013 Pearson Education, Inc. 102

5. The disaccharide that is found in milk and milk products is_______. sucrose maltose cellobiose lactose © 2013 Pearson Education, Inc.

5. The disaccharide that is found in milk and milk products is_______. sucrose maltose cellobiose lactose © 2013 Pearson Education, Inc.

maltose lactose starch cellulose 6. Which of the following yields a sugar other than glucose upon complete hydrolysis? maltose lactose starch cellulose © 2013 Pearson Education, Inc.

maltose lactose starch cellulose 6. Which of the following yields a sugar other than glucose upon complete hydrolysis? maltose lactose starch cellulose © 2013 Pearson Education, Inc.

galactose maltose lactose sucrose 7. Hydrolysis of which disaccharide gives glucose and fructose as products? galactose maltose lactose sucrose © 2013 Pearson Education, Inc.

galactose maltose lactose sucrose 7. Hydrolysis of which disaccharide gives glucose and fructose as products? galactose maltose lactose sucrose © 2013 Pearson Education, Inc.

amylose cellulose glycogen starch 8. Which of the following carbohydrates would not yield maltose if it were partially hydrolyzed? amylose cellulose glycogen starch © 2013 Pearson Education, Inc. 109

amylose cellulose glycogen starch 8. Which of the following carbohydrates would not yield maltose if it were partially hydrolyzed? amylose cellulose glycogen starch © 2013 Pearson Education, Inc. 110

9. Saccharin is_______. a pentose a hexose an aldose none of these © 2013 Pearson Education, Inc.

9. Saccharin is_______. a pentose a hexose an aldose none of these © 2013 Pearson Education, Inc.

10. The polysaccharide that is not digestible by humans is_______. glycogen cellulose amylose amylopectin © 2013 Pearson Education, Inc.

glycogen cellulose amylose amylopectin 10. The polysaccharide that is not digestible by humans is_______. (remember it has beta links that we cannot digest) glycogen cellulose amylose amylopectin © 2013 Pearson Education, Inc.

maltose amylose glycogen cellulose 11. In which of the following are monosaccharide units not joined by alpha linkages? maltose amylose glycogen cellulose © 2013 Pearson Education, Inc. 115

maltose amylose glycogen cellulose 11. In which of the following are monosaccharide units not joined by alpha linkages? maltose amylose glycogen cellulose © 2013 Pearson Education, Inc. 116

12. The most highly branched polysaccharide is_______. amylose glycogen amylopectin cellulose © 2013 Pearson Education, Inc.

12. The most highly branched polysaccharide is_______. amylose glycogen amylopectin cellulose © 2013 Pearson Education, Inc.

the length of the polysaccharide 13. Which structural feature prevents the human digestion of cellulose? the length of the polysaccharide the branches formed in the polysaccharide the β form of the linkages the galactose units in the polysaccharide © 2013 Pearson Education, Inc.

the length of the polysaccharide 13. Which structural feature prevents the human digestion of cellulose? the length of the polysaccharide the branches formed in the polysaccharide the β form of the linkages the galactose units in the polysaccharide © 2013 Pearson Education, Inc.

14. Which compound contains a -acetal linkage? amylose glycogen lactose maltose © 2013 Pearson Education, Inc. 121

14. Which compound contains a -acetal linkage? amylose glycogen lactose maltose © 2013 Pearson Education, Inc. 122

15. Which compound contains -acetal linkages and 1,6 branching? amylose cellulose glycogen sucrose © 2013 Pearson Education, Inc. 123

15. Which compound contains -acetal linkages and 1,6 branching? amylose cellulose glycogen sucrose © 2013 Pearson Education, Inc. 124