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

Topics…

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…

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 monosaccharides you need to know…

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

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

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

Which is sucrose? a b 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?.. a b 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?... a B (amylopectin) c

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

Multiple Choice Questions…

a) double bond b) hydroxyl group c) carbonyl group d) carboxyl group 1.The name of the functional group of aldehydes and ketones is a(n)_______.

a) double bond b) hydroxyl group c) carbonyl group d) carboxyl group

a)3-bromobutanal b)2-bromobutanal c)3-bromobutanone d)2-bromobutanone 2. The IUPAC name for the following compound is_______. Br O CH 3 CHCH 2 CH

2. The IUPAC name for the following compound is_______. Br O CH 3 CHCH 2 CH a)3-bromobutanal (remember the aldehyde carbon is carbon #1) b)2-bromobutanal c)3-bromobutanone d)2-bromobutanone

3. The common name for the following compound is_______. O CH3CH a) methyl aldehyde b) methyl ketone c) formaldehyde d) acetaldehyde

3. The common name for the following compound is_______. O CH3CH a) methyl aldehyde b) methyl ketone c) formaldehyde d) Acetaldehyde (acet is another root name for 2 carbons)

4. The compound CH 3 COCH 3 is_______. a) formic acid b) formaldehyde c) acetone d) methanone

4. The compound CH 3 COCH 3 is_______. a) formic acid b) formaldehyde c)Acetone (the book uses the abbreviation CO for a ketone)… d) methanone

5. The condensed structural formula of the alcohol needed to give 2-butanone is_______. a)CH 3 CH 2 CHCH 3 b)CH 3 CH 2 CH 2 CH 2 OH c)CH 3 CH 2 CH 2 OH d)CH 3 CHCH 3 OH

5. The condensed structural formula of the alcohol needed to give 2-butanone is_______. a)CH 3 CH 2 CHCH 3 b)CH 3 CH 2 CH 2 CH 2 OH c)CH 3 CH 2 CH 2 OH d)CH 3 CHCH 3 OH

6.The IUPAC name for the following compound is______. a)2-chloro-4-hexanone b)2-chloro-4-hexanal c)5-chloro-3-hexanone d)5-chloro-3-hexanal O Cl CH 3 CH 2 CCH 2 CHCH 3

a)2-chloro-4-hexanone b)2-chloro-4-hexanal c)5-chloro-3-hexanone (count from the left, b/c it is closer to the carbonyl group) d)5-chloro-3-hexanal 6.The IUPAC name for the following compound is______. O Cl CH 3 CH 2 CCH 2 CHCH 3

7. The structural formula of the organic product when hydrogen and a nickel catalyst reduce the following is_______. O CH 3 CCH 3 a)CH 3 CH 2 OH OH b)CH 3 CHCH 3 c)CH 3 CH 2 CH 2 OH d)CH 3 OH

7. The structural formula of the organic product when hydrogen and a nickel catalyst reduce the following is_______. O CH 3 CCH 3 a)CH 3 CH 2 OH OH b)CH 3 CHCH 3 c)CH 3 CH 2 CH 2 OH d)CH 3 OH Remember, you add a hydrogen to the oxygen and a hydrogen to the carbon of the carbonyl in a reduction reaction…

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 Aldehydes oxidize to carboxylic acids.

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 Note: secondary alcohols oxidize to ketones. (You remove the hydrogen from the oxygen and the hydrogen from the carbon)…

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

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

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

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

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.

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.

3.The IUPAC name for the following compound is_______. CH 3 OCH 2 CH 3 methyl ethyl ether methoxyethane ethyl methyl ether ethoxymethane © 2013 Pearson Education, Inc.

3.The IUPAC name for the following compound is_______. CH 3 OCH 2 CH 3 methyl ethyl ether methoxyethane ethyl methyl ether (note this is correct alphabetically)! ethoxymethane © 2013 Pearson Education, Inc.

4.The formula for anesthetic “ether” is_______. CH 3 OCH 3 C 2 H 5 OH C 2 H 5 OC 2 H 5 CH 3 OC 2 H 5 © 2013 Pearson Education, Inc.

4.The formula for anesthetic “ether” is_______. CH 3 OCH 3 C 2 H 5 OH C 2 H 5 OC 2 H 5 CH 3 OC 2 H 5 © 2013 Pearson Education, Inc. Note: this is diethyl ether

6.Which alcohol is least soluble in water? CH 3 OH C 3 H 7 OH C 6 H 13 OH C 10 H 21 OH © 2013 Pearson Education, Inc.

6.Which alcohol is least soluble in water? (note: this is the one with the most carbons) CH 3 OH C 3 H 7 OH C 6 H 13 OH C 10 H 21 OH (this is the one with the most carbons)! (recall that increasing the # of carbons decreases the solubility in water) © 2013 Pearson Education, Inc.

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

8.All except which of the following compounds are soluble in water? ethanol 2-propanol acetone 1-hexanol (remember the cutoff is 5 carbons, this has 6)… © 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.

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.

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.

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.

13.Which grouping gives the proper order for increasing solubility in water? Recall: alcohols are the most soluble group so far, alkanes are the least! hexane < diethyl ether < butanol diethyl ether < butanol < hexane butanol < hexane < diethyl ether hexane < butanol < diethyl ether © 2013 Pearson Education, Inc.

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 (it is a ketose, it has a ketone at carbon #2) 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.

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

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 (recall lactose intolerance)… © 2013 Pearson Education, Inc. ______

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

6.Which of the following yields a sugar other than glucose upon complete hydrolysis? maltose Lactose (it gives glucose & galactose) starch cellulose © 2013 Pearson Education, Inc.

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

7.Hydrolysis of which disaccharide gives glucose and fructose as products? galactose maltose lactose Sucrose (it is made up of glucose & fructose) © 2013 Pearson Education, Inc.

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

8.Which of the following carbohydrates would not yield maltose if it were partially hydrolyzed? amylose Cellulose (recall this is the one that has all beta links. Maltose would have alpha links). glycogen starch © 2013 Pearson Education, Inc.

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

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.

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

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

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.

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.

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.

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

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

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