Chemistry Semester Exam: Specific Study Guide

Test 1st and 2nd period, Friday Dec. 19

Structure of Guide:
I. Environmental Chemistry by Subject
II. Everything Else by Subject – Guides, reactions, etc.
Some topics are accompanied by page references for the green
book.
All sections are completed in order of the outline given.

Notice that our most recent section, analytic chemistry, will be on the
exam, despite thoughts to the contrary. It is on the hand-written
outline Mrs. Nagel gave us.

I. Environmental Chemistry
1. Nitrates – pp.135-136
They are nutrients.
Food for algae/microfauna in water.
Present from fertilizer runoff; accumulated by eutrophication
--overproduced with lack of DO (dissolved oxygen) in lakes
Dying plants decompose anaerobically, build up, DO drops
(cycle)
 Nitrates are also present in drinking water, thanks to fertilizers
and acid rain.
They’re super-soluble, so HARD to remove (tertiary treatment
necessary: see next section)
Ingestion of too many nitrates can cause diseases in babies and
cancer in adults

2. Waste Water – p. 137

Pollutants: heavy metals, particulates, pesticides, dioxins,
nitrates, phosphates
To get fresh water from sea water: distillation or reverse osmosis

Treatment
--sometimes raw sewage is released! It breaks down,
but slowly…
1. Primary – removes solids and some oxygen-
demanding
waste
Uses filters and sedimentation tanks
Flocculation: removal of suspended matter
2. Secondary – removes most oxygen
demanding waste
Uses aerobic bacteria to degrade waste
Trickle filters and/or activated sludge
3. Tertiary – rarely done – removes heavy
metals, nitrates, phosphates
Precipitation of phosphates & ions
Removes nitrates using ion exchange,
denitrifying bacteria,
or algal ponds

3. Chlorination/Ozoneation

Formation of ozone: (UV catalyst)

O2  2O∙
O∙ + O2  O3
Depletion of ozone: (UV catalyst)
O3  O2 + O∙
O3 + O∙  2O2

Chlorination: Free-radical reaction: either

CCl2F2  CClF2 + Cl∙
Cl∙ + O3  ClO∙ + O2
ClO∙ + O∙  Cl∙ + O2
Or: Formation of halogenoalkanes
1. Initiating
Cl2 Cl∙ + Cl∙

2. Propagating (2 subs)
CH4 + Cl∙  CH3∙ + HCl
And CH3∙ + Cl2  CH3Cl + Cl∙

(Remember that the two propagating steps

eventually end in a Cl-free-rad)

3. Terminating (3 subs)
Cl∙ + Cl∙ Cl2
Or C2H5. ∙ C2H5.:C2H5
Or Cl∙ + C2H5. ∙ C2H5Cl

4. Greenhouse Effect and Gases

Gases: O3, CO2, H2O, CH4, NOx
Water and Carbon dioxide are by far the main gases.
Effect: Warming Earth by trapping/accumulation of radiation:
Short-wave sunlight reflects from Earth’s surface as Long-
wave and is then absorbed by the gas bonds
Too much greenhouse gas  over-heated atmosphere = global
warming!

5. Global Warming
Overaccumulation of CO2 and other gases  Temp. increase
But: Ice core samples imply fluctuation in temperature for
centuries!
Still, there’s been a gradual temperature increase.
Consequences: Agricultural/biodiversity changes; rising sealevels

Particulates reverse global warming: they SCATTER & reflect

radiation
Leading to cooling!

6. Photochemical smog
Occurs in “bowl-shaped” cities: less air circulation
Occurs with temperature inversion: layer of warm air above cool
air
 Trapped pollutants
 Photochemical: Reducing smog due to combustion
Yellow-brown, SO2 w/soot, etc.
Primary pollutants: NOx and VOC’s (volatile org’c cmpds)
 converted to secondary in sunlight: see table below

Formation of Secondary Pollutants

(pay especial attention to top and bottom rxns)
Nitrogen oxide NO2  NO + O∙
radicalization
Hydroxyl radicalization O∙ + H2O  2OH∙
Nitric Acid formation OH∙ + NO2 HNO3
Radical Propagation OH∙ + RH  R∙ + H2O
Peroxide Radical R∙ + O2  ROO∙
formation
PAN formation Peroxide radical + nitrogen
dioxide

II. General Chemistry

1. Isomers:
Remember double/triple bonds and functional groups (eg.
esters/carboxylic acids; ethers and alcohols and aldehydes; amines
and amides)

2. IR Spectra:
--Alcohol has a broad absorption at 3300 cm-1.
--Fingerprint region: Far right side of graph. Unique to each
molecule.
--Functional groups: special absorptions (like alcohols, above)

3. NMR:
Distinguish - # of peaks = H environments
Area under = ratio of # of H’s (using relative heights)
Splitting = # of neighbors for that environment (n+1)

4. Mass Spec:
Used to determine abundance of isomers, molecular mass, and
possible functional groups of a specific sample, thanks to
fragmentation

5. Chromatography
Adsorption: Adherence of a solute to a solid surface by
chemical bond or physical attraction
Partition: The ratio/equilibrium between mobile phase (elution
of the solute) and stationary phase (adsorption of the solute)
6. Retention factor:
Rf = Dist. Traveled by solute
Dist. Traveled by solvent

7. Processes of Chromatography
Paper: dot paper with solute, wet paper with solvent – observe
dist. Traveled
Thin Layer C: like paper, but on glass with a thin gel of silica as
mobile phase
Gas C: volatile sample is heated to gas in a capillary tube, with
Helium as inert aid
Column: Uses gel as mobile phase: eluent is poured over solute,
which then seeps through gel in tube – sample can be recovered
High-perform. Liquid C: Like gas, but more efficient—sample is
forced by pressure through a short column/tube, using silica particles
with alkane chains

8. Name/Draw Org’c compounds

Alkanes, Alkenes, Alkynes
Groups: carboxylic acids, esters, ethers, ketones, amines,
amides, nitriles, halogenoalkanes

9. Reactions: (v. important)

ADDITION
a. Hydrogenation – Alkene + H2  Alkane (Platinum catalyst)
b. Addition – Alkene + HX  Halogenoalkane
c. Halogenation – Alkene + X2  “Double-halogen”-alkane
d. Hydrolysis – Alkene + H2O  Alcohol

POLYMERISATION
Occurs through addition (using free radicals) or, more commonly,
condensation
Condensation also forms esters (carboxylic acid + alcohol =
ester)

OXIDISATION of ALCOHOLS (using Cr2O7-2)

a. Primary – Distillation  Aldehyde
Reflux  Carbox. Acid
b. Secondary – Distillation/Reflux  Ketone
c. Tertiary – NO REACTION!

10. Substitution Reactions (SN1 and SN2)

 (from Oct. 27-28 guide) – in reverse: SN2, then SN1

Both SN1 and SN2 require warm conditions.

SN2 – Subst’n, Nucleophilic, Bimolecular

Single-Step, produces Intermediate (that annoying thing in

brackets):

Notice that the OH group (reversed to show that the oxygen is

really the important thing) is sneaking up on the carbon from the
opposite side from the Br. That’s what SN2 reactions do: they give two-
timing (get it? 2-timing!! Ha ha…) OH groups the chance to grab those
poor primary carbons from behind.
If the carbons were surrounded with a bunch of buddies, then the
little SN2’s couldn’t do that: only a big, tough, “number one” SN1 can
(get it? Number 1!! Hee hee)… which brings us to:

SN1 – Subst’n, Nucleophilic, unimolecular

These are the fast, strong, two-step processes that beat up even
carbons that travel surrounded by lots of themselves (ie, tertiary):

1. SLOW step

2. FAST step
 Substitution involving nitrogen:

A NITRILE is an R-C≡N.
Name it using the longest chain including N, then add “-nitrile” at
end. So the root (eg ethanenitrile) is one word.

Remember formations of amines:

Ammonia is a nucleophile and forms amines with
halogenoalkanes. (SN2)
The cyanide ion forms a nitrile with halogenoalkanes (SN2) and
then reacts with H2 and nickel to form an amine.
It can THEN react with water to form a carboxylic acid and
ammonium ions.

Remember esterification (alcohol + acid) and formation of amides:

Acid + amine  amide
(name with N prefix followed by normal name, then –amide)

4. Elimination Reactions: Formation of Alkenes

E2: Transition (intermediate) state; E1: Carbocation –like SN.
Occur in HOT conditions with concentrated, alcoholic NaOH

E1: Tertiary Carbon: halogen detaches, forms carbocation

Then (step 2) a hydrogen on the cation joins OH- and forms
water, while the extra electrons from the lost H form a double bond
between the Carbons!
It’s like the halogen is a shoe, and it comes off. So the foot (the
H) goes to join a massage parlor (the OH group) and the legs are left to
double bond themselves, unable to walk but now stronger than ever.
…yes.

E2: Primary Carbon: Halogen detaches AS the hydrogen leaves for the
OH, and electrons join the carbons as usual. One step.
It’s like a clean breakup. The halogen and hydrogen both leave
the carbons for greener pastures and better fish, so the electrons are
the rebound relationship—which is really clingy and double-bonded,
because the carbons are lonely and traumatized.
Got it?
_______________

That’s it for this guide! Please be sure to look over your notes,
especially on reactions. The theoretical explanations may not have
fixed information as well as complicated drawings might have.
Remember that your green book is your friend. It loves you!
Good luck on the exam, everyone. Peace on earth!