Chemistry Final Exam

What makes a molecule organic?

If it contains carbon.

Any atom that is not carbon or hydrogen in an organic compound?

A Heteroatom.

Tetrahedral angle…

109.5 degrees

Linear bond angle…

180 degrees

Bent bond angle…

104.5 degrees

Trigonal planar bond angle…

120 degrees

Have a carbon-carbon double bond (C=C) functional group

Alkene

Compound represented by a six-member carbon ring with three double bonds

Aromatic ring

Contains a carbon group bonded to e hydroxyl (R-OH)

Alcohol

Contans a carbon-nitrogen bond (R-NHx)

Amine (N for Amine!)

Contains two carbon groups bonded to the same oxygen (R-O-R’)

Ether

Contains an -OH group bonded directly to the carbonyl group (R-COOH)

Carboxylic acid

Has a hydrogen atom bonded directly to the carbonyl group (R-CHO)

Aldehyde

Contains an amino group bonded directly to the carbonyl group (R-CONHx)

Amide

Contains a -OR group bonded directly to the carbonyl carbon (R-COOR’)

Ester

Is CH3(CH2)6CH3 water soluble or organic soluble?

Soluble in organic solvents because it only contains carbon and hydrogen

Is CH3CH2OH water soluble or organic soluble?

Water soluble because it contains oxygen, and “like dissolves like”!

Hydrocarbons with the maximum number of hydrogen atoms for each carbon

Alkanes

Chains of alkanes

Acyclic

How many hydrogen atoms are present on an acyclic alkane with seven carbons?

16 (Cn + H2n + 2 = 7 × 2 = 14 + 2 = 16)

Compounds having the same molecular formula but different structures

Isomers

Where can product from petroleum be located?

Everywhere

Considering C5H12, C7H16, and C10H22, which has the highest boiling point?

Decane because greater intramolecular forces equals a higher boiling point

Considering C5H12, C7H16, and C10H22, which has the lowest melting point?

Pentane because weaker intramolecular forces equals lower melting points

Hydrocarbons containing fewer than the maximum number of hydrogen bonds per carbon

Unsaturated

What kind of hydrocarbon is (CH3)2CHC -triple bond- CCH2C(CH3)3

Alkyne

Which best describes the formula C8H16?

Alkene because there is a double bond hidden in there!

Natural occurring fatty acids obtained from vegetables

Oils

Double bonds in fatty acids tend to be in what form?

Cis

Double bonds tend to do what to the melting point of a fatty acid?

Decrease it

Red pigment in tomatoes and watermelons that is an antioxidant

Lycopene

Which of the following is an antioxidant?: Vitamin D, Pancakes, or Vanillin

Vitamin D

What is the property of plastics that makes them so useful but bad for the environment?

Last forever

The tru structure of the benzene ring cannot be drawn with just a single 1, 3, 5-cyclohexatriene structure depiction as this does not show its true character. What property of benzene is responsible for this?

Resonance

Compund with an oxygen atom bonded to to organic group (R-O-R’)

Ether

Compound with an -OH (hydroxy) group bonded to tetrahedral carbon atom (R-OH)

Alcohol

Compound with an -X (halogen) group bonded to a saturated, alkane-like carbon (R-X)

Alkyl-halide

Compound with an -SH (sulfhydryl) group bonded to a saturated, alkane-like carbon (R-SH)

Thiol

Which compound has a higher boiling point?: CH3Ch2CH2OH or CH3CH2Ch2CH3

CH3Ch2CH2OH

Which compound is water soluble?: (CH3)3C-OH, CH2 = CHCH2CH3, or CH3CH2CH2CH2CH2CH2CH3OH

(CH3)3C-OH because its a low molecular weight alcohol

Rule for assigning major and minor dehydration products?

Zaitsev rule

Property of ethanol that makes it dangerous

CNS depressant, Chirrosis of the liver, Lack of coordination

Most notable thing about thiols

Distinct odor

What is one of the early anaesthetic methods used before ethers?

Excess alcohol and hitting the head

A molecule that is not superimposable on its mirror image

Chiral Cannot overlap!

What must be present for a molecule to have a chirality center?

Four different groups on a tetrahedral carbon

Baseball bat: Chiral or achiral?

Achiral

Screw: Chiral or achiral?

Chiral

Shoe: Chiral or achiral?

Chiral

Coffe mug: Chiral or achiral?

Achiral

Chair: Chiral or achiral?

Achiral

Seashell: Chiral or achiral?

Chiral

Why is it important to understand chirality for drug chemistry?

One enantiomer may have the desired effect while the other may do nothing of have harmful effects

Drug once used as a sedative and anti-nausea drug for pregnant women that resulted in extreme birth defects

Thalidomide

An equal mixture of both enantiomers of a molecule

Racemic

Naproxen, the pain reliever in Alleve has a dangerous enantiomer. What is its effect?

Liver toxin

What physical property allows for the identification of different enantiomers?

Optical activity

(S)-alanine is an amino acid used to synthesize comple proteins for muscle tissue. It has a melting point of 297 degrees Celsius and a specific rotation of +8.5.

Is it dextrorotary or levorotatory?

What is the specific rotations of the (R)-alanine?

What is the melting point of (R)-alanine?

Dextrorotary because +

-8.5 because counterclockwise is -

297 Celsius because melting points don’t change

In a molecule that has two adjacent chiral center, stereoisomer that are not mirror images can be formed. What are these called?

Diasteromers

Has two alkyl groups bonded to the carbonyl group

Ketone

Has at least one hydrogen atom bonded to the carbonyl group

Aldehyde

Bond shape for the carbonyl carbon?

Trigonal planar, 120 degrees

Reacts with proteins in the skin to produce a brown hue

Dihydroxyacetone

Once used as an anticancer drug as it is converted to glucose and benzaldehyde with highly toxic hydrogen cyanide (HCN) as a byproduct

Amygdalin

Starting material for resins and plastics. Is a disinfectant and preservative

Formaldehyde

Why cant ketones be oxidized to carboxylic acids?

There is no hydrogen attached to the carbonyl

Compund that has a carbonyl bonded to a nitrogen atom group, RCONR’2, where the R’ groups may be alkyl or a hydrogen

Amide

A compund with a carbonyl group bonded to an -OH group (RCOOH)

Carboylic acid

A compound with a carbonyl bonded to an -OR group (RCOOR’)

Ester

Common carboxylic acid found in some ant stings

Formic

Common carboxylic acid found in the odor of dirty socks and ginkgo seeds

Hexanoic

Common carboxylic acid found as the sour component of vinegar

Acetic

An ester used as a topical oral anasthetic

Benzocain

An amide that relieves pain and fever

Acetaminophen

An amide synthesized in the brain thought to induce sleep

Melatonin

Salts of carboxylic acid have spherical droplets called

Micelles