New User Special Price Expires in

Let's log you in.

Sign in with Facebook


Don't have a StudySoup account? Create one here!


Create a StudySoup account

Be part of our community, it's free to join!

Sign up with Facebook


Create your account
By creating an account you agree to StudySoup's terms and conditions and privacy policy

Already have a StudySoup account? Login here

Organic Chemistry; Chapter 14-17.2 Exam Study Guide

by: Caitlin McGee

Organic Chemistry; Chapter 14-17.2 Exam Study Guide CHEM 133

Marketplace > Western Carolina University > Organic Chemistry > CHEM 133 > Organic Chemistry Chapter 14 17 2 Exam Study Guide
Caitlin McGee
GPA 4.0

Preview These Notes for FREE

Get a free preview of these Notes, just enter your email below.

Unlock Preview
Unlock Preview

Preview these materials now for free

Why put in your email? Get access to more of this material and other relevant free materials for your school

View Preview

About this Document

This study guide is everything covered for Exam 2. Covering carbonyl groups, aldehydes, ketones, carbohydrates, carboxylic acids, esters, and a portion of lipids.
Survey of Chemistry 2
Utpal Chakraborty
Study Guide
Organic Chemistry, General Chemistry
50 ?




Popular in Survey of Chemistry 2

Popular in Organic Chemistry

This 15 page Study Guide was uploaded by Caitlin McGee on Tuesday October 4, 2016. The Study Guide belongs to CHEM 133 at Western Carolina University taught by Utpal Chakraborty in Fall 2016. Since its upload, it has received 4 views. For similar materials see Survey of Chemistry 2 in Organic Chemistry at Western Carolina University.

Similar to CHEM 133 at WCU

Popular in Organic Chemistry


Reviews for Organic Chemistry; Chapter 14-17.2 Exam Study Guide


Report this Material


What is Karma?


Karma is the currency of StudySoup.

You can buy or earn more Karma at anytime and redeem it for class notes, study guides, flashcards, and more!

Date Created: 10/04/16
CH.14 ALDEHYDES, KETONES, CHIRALITY  Carbonyl Group in o Aldehyde – bonded to at least one H atom o Ketone – bonded to 2 carbon groups o Aldehydes and ketones contain a carbonyl group that consists of a carbon–oxygen double bond with two groups of atoms attached to the carbon at angles of 120°  Polarity of Carbonyls o The oxygen atom with two lone pairs of electrons is much more electronegative than the carbon atom. o The carbonyl group has a strong dipole with a partial negative charge on the oxygen and a partial positive charge on the carbon. o The polarity of the carbonyl group strongly influences the physical and chemical properties of aldehydes and ketones. δ − δ  NAMING ALDEHYDES + o Replace alkane “e” with “al” o No number because it’s always on the end  HYDRATION REACTIONS o Alkene reacts with water (H-OH) to make an alcohol o H from the water = goes to the carbon in the double bond with more H’s o OH from the water = goes to the second carbon in the double bond (the one with less H) o Also, this breaks the double bond. So it goes to single bonds.  DEHYDRATION OF ALCOHOLS o Opposite of hydration o Loss of –H and –OH = makes an alkene and water molecule o Has to have heat and acid catalyst to happen  OXIDATION AND REDUCTION o Oxidation- increase the number of C-O bonds since you’re gaining an O or losing a H o 1 (Primary) alcohol can oxidize to an aldehyde. Aldehydes oxidize to a carboxylic acid. o 2 (Secondary) alcohol oxidize to a ketone. o 3 (tertiary) alcohols DO NOT OXIDIZE o Reduction- reduces the number of bonds BETWEEN C and O atoms o Aldehydes oxidized to carboxylic acids, ketones don’t oxidize  Naming Ketones o the alkyl groups bonded to the carbonyl group are named as substituents. o Start numbering carbons at the carbonyl group (end)  Cyclic ketones o Cyclo is at the beginning o any substituent is located by numbering the ring starting with the carbonyl carbon as carbon 1. o the ring is numbered in the direction to give substituents the lowest possible numbers.  Aldehydes and ketones contain a polar carbonyl group  Aldehydes and ketones containing 3 to 10 carbon atoms are liquids.  Aldehydes and ketones have dipole–dipole interactions between polar groups o higher boiling points than alkanes and ethers of similar mass as a result of dipole–dipole interactions. o lower boiling points than alcohols of similar mass because they do not form hydrogen bonds.  Tollens’ test o Tells difference between aldehyde and ketone o Tollens reagent (Ag and ammonia) will oxidize aldehydes to carboxylic acid but not ketones (because they don’t oxidize anyway). Aldehydes gets a silver mirror layer on the inside of the container  Benedicts test o Turns brick red when added to an aldehyde with adjacent OH group. Negative (blue) with simple aldehydes and ketones o Can see if glucose is in urine  Aldehydes are reduced to primary alcohols, and ketones are reduced to secondary alcohols.  HEMIACETAL AND ACETAL o Aldehyde or ketone + alcohol + acid catalyst = hemiacetal o Unstable hemiacetal + second molecule of the alcohol = stable acetal and water  Aldehydes are often more reactive than ketones because the carbonyl carbon is more positive.  Cyclic hemiacetals can be isolated  Five- and six-atom cyclic hemiacetals and acetals are more stable than their open-chain isomers.  Glucose forms a six-carbon cyclic hemiacetal when the hydroxyl group on carbon 5 bonds with the carbonyl group on carbon 1. o An alcohol can add to the cyclic hemiacetal and form a cyclic acetal. This reaction explains how sugar molecules can link together and form disaccharides and polysaccharides.  Acetal bond (red) and hemiacetal bond (shown in green)  ACHIRAL = same thing  CHIRAL = mirror flipped  STEREOISOMERS - In stereoisomers, the atoms are bonded in the same sequence but differ in the way they are arranged in space. CHAPTER 15: CARBOHYDRATES NOTES  Carbohydrates AKA saccharides AKA sugars o Made from carbon, hydrogen, and oxygen o Gives us lots of energy  Types of carbs are: o Monosaccharides (simplest) o Disaccharides (2 monosaccharides) o Polysaccharides (3 monosaccharides or more) MONOSACCHARIDES  Have lots of hydroxyl (-OH) groups attached to 3-8 carbons in a chain o If that have a aldehyde group (H-C=O), they are ALDOSES o If they have a ketone group (C=O), they are KETOSES  Names: triose (3 carbons), tetrose (4 carbons), pentose (5 carbons), Hexose (6 carbons), aldo for aldehydyes, keto for ketones  Fischer Projections: represents carbohydrates. D-glucose, D-galactose, and D-fructose are most important monosaccharides. Shows us D or L configuration. Puts aldehyde group (H-C=O) at top. Has the –H and –OH going down the middle. Then –CH2OH at the bottom. If –HO is on the left, its L. If the –OH is on the right, its D.  Assigned from the carbon farthest from the carbonyl group.  D-Glucose o Is known as dextrose and blood sugar in body. Found in fruits, veggies, corn syrup, and honey  D-Galactose o Found in milk. Important for brain and nervous system. Galactosemia is medical condition where the builds up in body and kills you o Galactose is an aldohexose  D-Fructose o Sweetest of the carbs. Made from hydrolysis of sucrose. o Fructose is a ketohexose  Can check if glucose is in urine using benedicts test.  Haworth Structures: produced from the reaction of a carbonyl group and a hydroxyl group in the same molecule. o Turn the Fischer projection 90 DEGREES CLOCKWISE. o Bond the O on carbon #5 to carbon #1. Carbons #2 and #3 will form the base (bottom)  Draw the — OH group on carbon 1 below the ring to give the α anomer(OPPOSITE; ALPHA IS ON BOTTOM) or above the ring to give the β anomer(OPPOSITE; BETA IS ON TOP).  When placed in a solution, cyclic structures open and close and a- glucose converts to B-glucose and vice versa.  Oxidation o Produced from the oxidation of the aldehyde. o Named by replacing the “ose” ending with “onic acid” o A carb that reduces another substance is called a reducing sugar  Reduction o Converts an aldehyde group to alcohol producing sugar alcohols AKA alditols  Reducing sugars o Named by replacing the “ose” ending with “itol” o Used as sweeteners in sugar-free products like diet drinks and sugarless gums DISACCHARIDES  2 monosaccharides linked together  Formed when 2 monosaccharides combine in a dehydration reaction  Most common are maltose, lactose, and sucrose  MALTOSE aka malt sugar o Composed of 2 a-d-glucose molecules o Obtained from the hydrolysis of starch o Used in cereal, candies, and brewing  LACTOSE o Found in milk and milk products o Made of β-D-galactose and α- or β-D-glucose.  SUCROSE aka table sugar o consists of α-D-glucose and β-D-fructose. o Cannot form an open chain or be oxidized, cannot react with Beneditcts reagent, and is not a reducing sugar  Sucralose aka Splenda: made from sucrose by replacing some of the hydroxyl groups with chlorine atoms  Aspartame – marketed as NutraSweet or Equal. Noncarbohydrate sweetener, very sweet.  Neotame – artificial sweetener. Modified aspartame structure. Very sweet. 10,000 times sweeter than sucrose  Saccharin aka Sweet’N Low – banned in Canada because it is linked to bladder tumors. POLYSACCHARIDES  3 or more monosaccharides are joined together  STARCH o Storage form of glucose in plants, found as insoluble granules in rice, wheat, potatoes, beans, and cereals o Composed of two kinds of polysaccharides: amylose and amylopectin o Hydrolyzes easily in water and acid to give small saccharides aka dextrins then hydrolyzes to maltose and then glucose o AMYLOPECTIN o Makes up 80% of starch o Contain glucose molecules connected by α-(1 4)- and α- (16)-glycosidic bonds. o Digested by amylase in saliva and maltase in intestines o Provide about 50% of our nutritional calories from the glucose obtained in digestion o ANIMAL STARCH: GLYCOGEN o Polymer of glucose; stored in liver/muscle of animals o Slowly hydrolyzed to maintain blood sugar and maintain energy between meals; storage form of glucose o Similar to amylopectin  CELLULOSE o Major structural unit of wood and plants o Made of glucose units in unbranched chains with β-(14)- glycosidic bonds. o Insoluble in water(cannot form hydrogen bonds with water) o cannot be digested by humans because humans cannot break down β-(14)-glycosidic bonds. CHAPTER 16: CARBOXYLIC ACIDS AND ESTERS CARBOXYLIC ACIDS  contains a carboxyl group, which is a hydroxyl group (-OH) attached to the carbon in a carbonyl group  the “e” in the alkane name is replaced with “oic acid”  substituents are numbered from the carboxyl group, which is carbon 1  for benzoic acid, the placement of substituents is shown using the prefixes ortho, meta, and para.  can be prepared from primary alcohols or aldehydes  ALPHA HYDROXY ACIDS (AHAs) o Found in fruits, milk, and sugar cane o Can be used to remove acne scars and in skin peels in high concentrations  Carboxylate salts, sodium propionate, and sodium benzoate are used as flavor enhancers and is added to foods to inhibit the spoilage of the food  Strongly polar because they have a hydroxyl group (-OH) and a carbonyl group (C = O)  Also has a higher boiling point (118 degrees C); attributed to the formation of dimers between 2 carboxylic acids. 2 H bonds form between their carbonyl groups = increasing mass = increase in temp required to reach boiling point  Will form hydrogen bonds with many water molecules. 1-5 carbons = very soluble in water. 5 and more are less soluble.  Are weak acids.  Carboxylate salts are the product of neutralization of the acid with a strong base. Name is changed be replacing “oic acid” to “ate” o Solids at room temperature o Soluble in water o High melting points  MSG is added to enhance flavor. Could cause headaches  In the citric acid cycle (Krebs cycle), carboxylates are oxidized and decarboxylated (loss of CO2)to give energy to cells ESTERS  Salicin helps to relieve pain but it hurts the stomach. An ester of that same compound, acetylsalicylic acid (aspirin), is just as good  Synthesized from the reaction of a carboxylic acid and alcohol  Gives the aroma/flavor for bananas, oranges, strawberries, pineapples  Esterification o Reaction of a carboxylic acid and alcohol in the presence of an acid catalyst and heat = MAKING AN ESTER o the replacement of the hydrogen atom in the carboxylic acid — OH group with an alkyl group from an alcohol.  Methyl Salicylate (oil of wintergreen) has a minty odor. Used in skin ointments. Can pass through skin and can soothe sore muscles by producing heat  Dacron (plastic) – wrinkle resistant usage. Artificial blood vessels that doesn’t clot blood. Also makes mylar and plastic known as PETE for plastic bottles  The name of an ester consists of two words: o The first word indicates the alkyl part from the alcohol. o The second word is the carboxylate name of the carboxylic acid.  Change the ic acid of the acid name to ate.  Have high boiling points but lower than alcohols and carboxylic acids of similar mass  Soluble= 2-5 carbons. Non soluble (or less soluble)= 5 or more carbons  ACID HYDROLYSIS (acid catalyst and heat required) o Ester reacts with water to make carboxylic acid and alcohol  BASE HYDROLYSIS aka SAPONIFICATION o Reaction of an ester with a strong base in the presence of heat o Makes carboxylate salt and alcohol LIPIDS – up to 17.3  Biomolecules that contain fatty acids or a steroid nucleus. Lipids are nonpolar.  Soluble in organic solvents – but NOT water  Lipids are characterized by their structures  Waxes, triacylglycerols, glycerophospholipids, and sphingolipids can be hydrolyzed to give fatty acids and other molecules  Steroids do not contain fatty acids and cannot be hydrolyzed. Will have 4 fused carbon rings  Saturated fatty acids – stack closely  Unsaturated fatty acids – do not closely together  FATTY ACIDS o Long, unbranched carbon chains with a carboxylic acid group on the end o Typically 12-18 carbon atoms long (making it insoluble) o saturated when they do not contain C = C double bonds in the carbon chain. o unsaturated when they contain C = C double bonds in the carbon chain. o monounsaturated, with only one double C = C bond in the carbon chain. o polyunsaturated, with at least two double C = C bonds in the carbon chain. o Humans are capable of synthesizing some fatty acids from carbs or other fatty acids but can’t make linoleic acid, linolenic acid, or arachidonic acid. Since they can’t be made, they are called essential fatty acids because they are essential in our diets.  SATURATED FATTY ACIDS o contain only single C — C bonds and fit close together in a regular pattern, with strong dispersion forces between carbon chains. o require a significant amount of energy and high temperatures to separate and melt.  Prostaglandins o Hormone-like substances; polyunsaturated fatty acid with 20 carbon atoms o Differ according to the substituents on the 5-carbon ring o Can lower or raise blood pressure, can stimulate contraction and relaxation of the muscle in the uterus o NSAIDs block production of prostaglandins, decreasing pain and inflammation o Unsaturated fats such as those in vegetable oils and fish are recognized as more beneficial to health than saturated fats. o Vegetables contain omega-6 acids, meaning the first double bond occurs at carbon 6 counting from the methyl end of the carbon chain. Examples of omega-6 acids are linoleic and arachidonic acids. Fish have high levels of omega-3 acids, meaning the first double bond occurs at carbon 3, counting from the methyl end of the chain.


Buy Material

Are you sure you want to buy this material for

50 Karma

Buy Material

BOOM! Enjoy Your Free Notes!

We've added these Notes to your profile, click here to view them now.


You're already Subscribed!

Looks like you've already subscribed to StudySoup, you won't need to purchase another subscription to get this material. To access this material simply click 'View Full Document'

Why people love StudySoup

Jim McGreen Ohio University

"Knowing I can count on the Elite Notetaker in my class allows me to focus on what the professor is saying instead of just scribbling notes the whole time and falling behind."

Jennifer McGill UCSF Med School

"Selling my MCAT study guides and notes has been a great source of side revenue while I'm in school. Some months I'm making over $500! Plus, it makes me happy knowing that I'm helping future med students with their MCAT."

Bentley McCaw University of Florida

"I was shooting for a perfect 4.0 GPA this semester. Having StudySoup as a study aid was critical to helping me achieve my goal...and I nailed it!"

Parker Thompson 500 Startups

"It's a great way for students to improve their educational experience and it seemed like a product that everybody wants, so all the people participating are winning."

Become an Elite Notetaker and start selling your notes online!

Refund Policy


All subscriptions to StudySoup are paid in full at the time of subscribing. To change your credit card information or to cancel your subscription, go to "Edit Settings". All credit card information will be available there. If you should decide to cancel your subscription, it will continue to be valid until the next payment period, as all payments for the current period were made in advance. For special circumstances, please email


StudySoup has more than 1 million course-specific study resources to help students study smarter. If you’re having trouble finding what you’re looking for, our customer support team can help you find what you need! Feel free to contact them here:

Recurring Subscriptions: If you have canceled your recurring subscription on the day of renewal and have not downloaded any documents, you may request a refund by submitting an email to

Satisfaction Guarantee: If you’re not satisfied with your subscription, you can contact us for further help. Contact must be made within 3 business days of your subscription purchase and your refund request will be subject for review.

Please Note: Refunds can never be provided more than 30 days after the initial purchase date regardless of your activity on the site.