Chapter 7

Alkenes and Alkynes I:

Properties and
Synthesis.
Elimination Reactions
of Alkyl Halides
1. Introduction
 Alkenes
● Hydrocarbons containing C=C
● Old name: olefins

CH2OH

Vitamin A H3C

H3C

H H
Cholesterol
HO
Ch.
  Alkynes
● Hydrocarbons containing C≡C
● Common name: acetylenes
H
N O I Cl
C
O C O
Cl
F3C C Cl
C
Cl
Efavirenz Haloprogin
(antiviral, AIDS therapeutic) (antifungal, antiseptic)

Ch.
2. The (E) - (Z) System for Desig
ating Alkene Diastereomers
 Cis-Trans System
● Useful for 1,2-disubstituted
alkenes
● Examples:
H Br
(1) Cl vs Cl
Br H
H H
trans -1-Bromo- cis -1-Bromo-
2-chloroethene 2-chloroethene
Ch.
 ● Examples
H
(2) vs
H
H H
trans -3-Hexene cis -3-Hexene

Br
(3) Br Br vs
Br
trans -1,3- cis -1,3-
Dibromopropene Dibromopropene
Ch.
 (E) - (Z) System
● Difficulties encountered for
trisubstituted and
tetrasubstituted alkenes
CH3
e.g. Cl cis or trans?
Br
H
Cl is cis to CH3
and trans to Br
Ch.
 The Cahn-Ingold-Prelog (E) - (Z)
Convention

● The system is based on the

atomic number of the attached
atom

● The higher the atomic number,

the higher the priority

Ch.
 The Cahn-Ingold-Prelog (E) - (Z)
Convention
● (E) configuration – the highest
priority groups are on the opposite
side of the double bond
 “E ” stands for “entgegen”; it
means “opposite” in German
● (Z) configuration – the highest
priority groups are on the same
side of the double bond
 “Z ” stands for “zusammen”; it
means “together” in German
Ch.
● Examples
CH3
Cl 1
2 Br
H
On carbon 2: Priority of Br > C
On carbon 1: Priority of Cl > H
 highest priority groups
are Br (on carbon 2)
and Cl (on carbon 1)
Ch.
● Examples CH3
Cl
Br
H
 (E )-2-Bromo-1-chloropropene

Br
Cl
CH3
H
 (Z )-2-Bromo-1-chloropropene
Ch. 7
 ● Other examples

H (E )-1,2-Dichloroethene
(1) Cl [or trans-1,2-Dichloroethene]
2
1 Cl
H C1: Cl > H
C2: Cl > H

2 (Z )-1-Bromo-1,2-dichloroethene
Cl
(2) 1 Cl
Br C1: Br > Cl
C2: Cl > H
Ch. 7
 ● Other examples

Br
3 1
4
(3) 2
7 5
8 6 (Z )-3-Bromo-4-tert-butyl-3-octene

C3: Br > C
C4: tBu > nBu

Ch. 7
3. Relative Stabilities of Alkene
 Cis and trans alkenes do not have
the same stability
crowding

R R H R
C C C C
H H R H

Less stable More stable

Ch. 7
3A. Heat of Reaction

Pt
C C + H H C C
H H

 Heat of hydrogenation
● ∆H° ≃ -120 kJ/mol

Ch. 7
 + H2

7 kJ/mol
+ H2
H° = -127 kJ/mol
Enthalpy

5 kJ/mol + H2

H° = -120 kJ/mol

H° = -115 kJ/mol

≈ ≈ ≈

Ch. 7
3B. Overall Relative Stabilities of
Alkenes
 The greater the number of
attached alkyl groups (i.e., the
more highly substituted the
carbon atoms of the double bond),
the greater the alkene’s stability.

Ch. 7
  Relative Stabilities of Alkenes

R R R R R H R H R R R H H H
> > > > > >
R R R H R H H R H H H H H H
tetra- tri- di- mono- un-
substituted substituted substituted substituted substituted

Ch. 7
 Examples of stabilities of alkenes

(1) >

(2) >

Ch. 7
4. Cycloalkenes
 Cycloalkenes containing 5 carbon
atoms or fewer exist only in the
cis form

cyclopropene cyclobutene cyclopentene

Ch. 7
 Trans – cyclohexene and trans –
cycloheptene have a very short
lifetime and have not been
isolated

cyclohexene Hypothetical
trans - cyclohexene
(too strained to exist at r.t.)

Ch. 7
 Trans – cyclooctene has been
isolated. The molecule is chiral
and exists as a pair of
enantiomers.

cis - cyclooctene trans - cyclooctenes

Ch. 7
5. Synthesis of Alkenes via
Elimination Reactions
 Dehydrohalogenation of Alkyl
H
Halides
H H H H
base
C C
H -HX
X H H
H
 Dehydration of Alcohols
H
H H H+, heat H H
C C
H OH -HOH H H
H
Ch. 7
6. Dehydrohalogenation of Alky
Halides
 The best reaction conditions to
use when synthesizing an alkene
by dehydrohalogenation are
those that promote an E2
mechanism
H
E2
B: C C C C + B:H + X
X
Ch. 7
6A. How to Favor an E2 Mechanism
 Use a secondary or tertiary alkyl
halide if possible. (Because steric
hindrance in the substrate will
inhibit substitution)
 When a synthesis must begin with
a primary alkyl halide, use a bulky
base. (Because the steric bulk of
the base will inhibit substitution)

Ch. 7
 Use a high concentration of a
strong and non-polarizable base,
such as an alkoxide. [Because a
weak and polarizable base would
not drive the reaction toward a
bimolecular reaction, thereby
allowing unimolecular processes
(such as SN1 or E1 reactions) to
compete.]
Ch. 7
 Sodium ethoxide in ethanol
(EtONa/EtOH) and potassium tert-
butoxide in tert-butyl alcohol
(t-BuOK/t-BuOH) are bases
typically used to promote E2
reactions

 Use elevated temperature

because heat generally favors
elimination over substitution.
(Because elimination reactions are
entropically favored over Ch. 7
6B. Zaitsev’s Rule
 Examples of
dehydrohalogenations where only
a single elimination product is
possibleEtONa
(1) o
(79%)
Br EtOH, 55 C
EtONa
(2) o
(91%)
Br EtOH, 55 C
t -BuOK
(3) ( )
Br ( ) (85%)
n t -BuOH, 40oC n

Ch. 7
 H
 Rate =k H3C C CH3 EtO
Br (2nd order overall)
 bimolecular
a
̶̶̶ H
B Ha Hb
2-methyl-2-butene

Br
b
̶̶̶ H
2-methyl-1-butene
Ch. 7
 When a small base is used (e.g.
⊖ ⊖
EtO or HO ) the major product
will be the more highly substituted
alkene (the more stable alkene).
Examples:
a
H H b
EtONa
(1) +
EtOH
70oC
Br 69% 31%
(eliminate Ha) (eliminate Hb)
Br EtOK
(2) + +
EtOH
51% 18% 31%

69%

Ch. 7
 Zaitsev’s Rule
● In elimination reactions, the
more highly substituted alkene
product predominates
 Stability of alkenes
Me Me Me Me Me H
C C > C C > C C
Me Me Me H H Me

Me Me Me H
> C C > C C
H H H H
Ch. 7
Mechanism for an E2 Reaction
Et O Et O
H CH3 H CH3
α  H3C CH3
C C CH3 C C CH3 C C
H3C β H3C  H CH3
H Br H Br +

Et OH + Br
EtO⊖ removes Partial bonds
in the C=C is fully
a  hydrogen;
transition formed and
C−H breaks;
state: C−H and the other
new  bond
C−Br bonds products are
forms and Br
break, new  EtOH and
begins to
depart C−C bond Br⊖
Ch. 7
 
O Et
H3C H
 CH3CH2 C C
Et O  H
CH3 Br H
H
C C CH3
H3C
H Br
 G1‡
Free Energy

G2‡
CH3
CH3 -
CH3CH2 C CH2 + EtOH + Br
EtO- + CH3CH2 C CH3
Br
CH3
-
CH3CH C CH3 + EtOH + Br

Reaction Coordinate
Ch. 7
6C. Formation of the Less Substitu
Alkene Using a Bulky Base
 Hofmann’s Rule
● Most elimination reactions
follow Zaitsev’s rule in which
the most stable alkenes are the
major products. However,
under some circumstances, the
major elimination product is
the less substituted, less stable
alkene
Ch. 7
 ● using a bulky base
EtO CH3CH CHCH3 (80%)
+
(small) CH3CH2CH CH2 (20%)

CH3CH2CHCH3
Br t CH3CH CHCH3 (30%)
BuO
+
(bulky) CH3CH2CH CH2 (70%)
⊖
EtO
(small base)
H H H H t
BuO⊖

H C C C C H (bulky base)
H H Br H
Ch. 7
 Zaitsev Rule vs. Hofmann Rule

● Examples

Ha Hb
(1) +

Br a b
(eliminate H ) (eliminate H )
o
NaOEt, EtOH, 70 C 69% 31%

KOtBu, tBuOH, 75oC 28% 72%

Ch. 7
 ● Examples

b
H Br
Ha
(2) +

(eliminate Ha) (eliminate Hb)

o
NaOEt, EtOH, 70 C 91% 9%
t t o
KO Bu, BuOH, 75 C 7% 93%

Ch. 7
6D. The Stereochemistry of E2
Reactions
 The 5 atoms involved in the
transition state of an E2 reaction
(including the base) must lie in
the same plane
 The anti coplanar conformation is
the preferred transition state
geometry
● The anti coplanar transition
state is staggered (and
therefore of lower energy), Ch. 7
B B
H H LG
C C C C
LG

Anti coplanar Syn coplanar

transition state transition state
(preferred) (only with certain
rigid molecules)

Ch. 7
 Orientation Requirement
● H and Br have to be trans-
coplanar (also commonly called
anti periplanar)
● Examples
CH CH EtO CH CH
3 2 + 3 2

Br CH3 CH3
since: Br
CH3CH2 H Only H is
H trans-coplanar
H CH3
EtO to Br
Ch. 7
  E2 Elimination where there are
two axial β hydrogens
EtO (a) 1
H3C 4 CH(CH3)2

EtO b Ha 3 2
H 1-Menthene (78%)
1 CH(CH3)2 (more stable alkene)
H3C 4 H
3
2
H
H Cl
1
H3C 4 CH(CH3)2
Both Ha and Hb (b) 3 2
hydrogens are anti to
2-Menthene (22%)
the chlorine in this, the (less stable alkene)
more stable
conformation
Ch. 7
 E2 elimination where the only axial
β hydrogen is from a less stable
conformerH CH3
H Cl
CH(CH3)2 4
1
H3C 4 H 3 1 H
3
2 Cl 2
H H
H H H CH(CH3)2

Menthyl chloride Menthyl chloride

(more stable conformer) (less stable conformer)
Elimination is not Elimination is possible
possible for this for this conformation
conformation because because the green
no hydrogen is anti to hydrogen is anti to the
the leaving group chlorine
Ch. 7
 The transition state
for the E2
elimination is anti
CH3 coplanar
CH3
Cl Cl

H H H H
H H
H CH(CH3)2 H CH(CH3)2
OEt

2-Menthene H3C CH(CH3)2

(100%) Ch. 7
7. Acid-Catalyzed Dehydration o
Alcohols
 Most alcohols undergo
dehydration (lose a molecule of
water) to form an alkene when
heated with a strong acid
HA
C C C C + H2O
heat
H OH

Ch. 7
  The temperature and
concentration of acid required to
dehydrate an alcohol depend on
the structure of the alcohol
substrate
● Primary alcohols are the most
difficult to dehydrate. Dehydration
of ethanol, for example, requires
H H
concentrated sulfuric
conc. H and
H2SO4 acid Ha
Htemperature
C C H of 180°C C C + H2O
o
180 C H H
H OH
Ethanol (a 1o alcohol)
Ch. 7
 ● Secondary alcohols usually
dehydrate under milder conditions.
Cyclohexanol, for example,
dehydrates in 85% phosphoric acid
at 165–170°C
OH
85% H3PO4
+ H2O
165-170oC

Cyclohexanol Cyclohexene
(80%)

Ch. 7
 ● Tertiary alcohols are usually so
easily dehydrated that extremely
mild conditions can be used. tert-
Butyl alcohol, for example,
dehydrates in 20% aqueous sulfuric
acid at a temperature of 85°C
CH3 CH2
20% H2SO4
H3C C OH + H2O
CH3 85oC H3C CH3

tert-Butyl alcohol 2-Methylpropene

(84%)
Ch. 7
 ● The relative ease with which
alcohols will undergo
dehydration is in the following
order:
R R H
R C OH > R C OH > R C OH
R H H

3o alcohol 2o alcohol 1o alcohol

Ch. 7
  Some primary and secondary
alcohols also undergo
rearrangements of their carbon
CH3
skeletons during dehydration
H3C C CH CH3
CH3OH 85% H3PO4
3,3-Dimethyl-2-butanol 80oC

H3C CH3 H3C CH3

C C + C CHCH3
H3C CH3 H2C
2,3-Dimethyl-2-butene 2,3-Dimethyl-1-butene
(80%) (20%)
Ch. 7
● Notice that the carbon skeleton
of the reactant is
C
C C C C
C
while that of the product is
C C
C C
C C

Ch. 7
7A. Mechanism for Dehydration of
o
& 3 Alcohols: An E1 Reaction
 Consider the dehydration of tert-
butyl alcohol + H O
● Step 1 H

CH3 H H3C H
H3C C O H +H O H3C C O H
CH3 H CH3
protonated
alcohol
Ch. 7
 ● Step 2
H3C H CH3
H3C C O H C + H O
H3C CH3
CH3 H
a carbocation
● Step 3
H
CH2 H
H C H +
H O C + H O
C H3C CH3
H3C CH3 H H
2-Methylpropene

Ch. 7
7B. Carbocation Stability & the
Transition State
 Recall

R H H H
R C > R C > H C > H C
R R R H

3o > 2o > 1o > methyl

most least
stable stable

Ch. 7
Ch. 7
7C. A Mechanism for Dehydration o
Primary Alcohols: An E2 Reacti
protonated
1o alcohol alcohol
H H H
fast
C C O H +H A C C O H
H H acid H H
slow
catalyst
r.d.s
+A
H H
conjugate
H O + HA + C C
base
H alkene
Ch. 7
8. Carbocation Stability & Occurren
of Molecular Rearrangements
8A. Rearrangements during Dehy-
dration of Secondary Alcohols
CH3
H3C C CH CH3
CH3OH 85% H3PO4
heat
3,3-Dimethyl-2-butanol

H3C CH3 H3C CH3

C C + C CHCH3
H3C CH3 H2C
2,3-Dimethyl-2-butenol 2,3-Dimethyl-1-butene
(major product) (minor product)
Ch. 7
 Step 1
CH3 CH3
H H
H3C C C CH3 H3C C C CH3
CH3 O H CH3 OH2
H protonated
+ H O H alcohol

+ H O
H

Ch. 7
 Step 2

CH3 CH3
H
H3C C C CH3 H3C C CH CH3
H3C OH2 CH3
o
a 2 carbocation

+ H O
H

Ch. 7
 Step 3
CH3 CH3
 

H3C C CH CH3 H3C C CH CH3
CH3 CH3
2o carbocation transition state
(less stable)
3o carbocation
The less stable 2o (more stable)
carbocation CH3
rearranges to a more H3C C CH CH3
stable 3o
CH3
carbocation.
Ch. 7
 Step 4 (a)

A
(b) H

(a) or (b) H CH2 C C CH3

CH3CH3
(a) (b)
(major) (minor)
H3C CH3 H2C H
HA + C C C C CH3 + HA
H3C CH3 H3C CH3
more stable alkene less stable alkene
Ch. 7
 Other common examples of
carbocation rearrangements

● Migration of a methyl group

CH3 CH3
1 2 methanide
H3C C CH CH3 H3C C C CH3
migration
CH3 CH3
(1,2-methyl shift)
a 2o carbocation 3o carbocation

Ch. 7
 ● Migration of a hydride

H H
hydride
H3C C CH CH3 H3C C C CH3
migration
CH3 CH3
o
a 2 carbocation 3o carbocation

Ch. 7
8B. Rearrangement after Dehydration
of a Primary Alcohol
R
R H H C H
H
C C C O H +H A C C + H O +H A
E2 R H
H R H H
R R
C H C H
H H
C C +H A C C H + A
R H protonation
R H
R R
C H C H
+ H
A C C H C C H +H A
R deprotonation R
H H
Ch. 7
9. The Acidity of Terminal Alkyn
Acetylenic
hydrogen sp sp2 sp3
H H H H
H C C H C C H C C H
H H H H
pKa = 25 pKa = 44 pKa = 50

 Relative basicity of the conjugate

base
CH3CH2 > CH2 CH > CH CH
Ch. 7
  Comparison of acidity and basicity
of 1st row elements of the Periodic
Table
● >Relative
H OH H OR > H Cacidity
CR > H NH2 > H CH CH2 > H CH2CH3

pKa 15.7 16-17 25 38 44 50

● Relative basicity
OH < OR < C CR < NH2 < CH CH2 < CH2CH3

Ch. 7
10. Synthesis of Alkynes by
Elimination Reactions
 Synthesis of Alkynes by
Dehydrohalogenation of Vicinal
Dihalides

H H
2 NaNH2
C C C C
heat
Br Br

Ch. 7
 Mechanism

R
H H
NH2 H
R C C R Br
E2
Br Br R

NH2

R R

Ch. 7
 Examples
Br
H NaNH2
(1)
heat
H Br (78%)

Br H
Ph Br2 Ph
(2)
Ph CCl4 Ph NaNH2
H Br
(2 eq.)
heat

Ph Ph

Ch. 7
 Synthesis of Alkynes by
Dehydrohalogenation of Geminal
Dihalides
O Cl Cl
PCl5

R CH3 0oC R CH3

gem-dichloride

1. NaNH2 (3 equiv.),heat
2. HA

R H
Ch. 7
11. Terminal Alkynes Can Be
Converted to Nucleophiles fo
Carbon-Carbon Bond Formati
 The acetylide anion can be
prepared by
NaNH2
R H R Na + NH3
liq. NH3

Ch. 7
 Acetylide anions are useful
intermediates for the synthesis of
other alkynes

R R' X R R' + X

 ∵ 2nd step is an SN2 reaction,

o
usually only good for 1 R’ or
methyl halides
 2o and 3o R’ usually undergo E2
elimination Ch. 7
 Ph H
Examples
NaNH2
liq. NH3
I
Ph Na

CH3 I
H

SN2 E2

Ph CH3 Ph H
+ +
NaI + I

Ch. 7
11A. General Principles of Structur
and Reactivity Illustrated by t
Alkylation of Alkynide Anions
 Preparation of the alkynide anion
involves simple Brønsted–Lowry
acid–base chemistry

Ch. 7
 Once formed, the alkynide anion
is a Lewis base with which the
alkyl halide reacts as an electron
pair acceptor (a Lewis acid). The
alkynide anion can thus be called
a nucleophile because of the
negative charge concentrated at
its terminal carbon—it is a reagent
that seeks positive charge

Ch. 7
 The alkyl halide can be called an
electrophile because of the
partial positive charge at the
carbon bearing the halogen—it is
a reagent that seeks negative
charge

Ch. 7
12. Hydrogenation of Alkenes
H2
H H
Pt, Pd, or Ni
C C C C
solvent
heat and pressure

2 equiv.H2
H H
Pt, Pd, or Ni
C C C C
solvent
heatand pressure H H

 Hydrogenation is an example of
addition reaction
Ch. 7
 Examples
H
H2
H
Rh(PPh3)3Cl
(Wilkinson'scatalyst)

H
H2
Pd/C
H

Ch. 7
13. Hydrogenation: The Funct
of the Catalyst
 Hydrogenation of an alkene is an
exothermic reaction
● ∆H° ≃ -120 kJ/mol
hydrogenation
R CH CH R R CH2 CH2 R
+ H2 + heat

Ch. 7
Ch. 7
13A. Syn and Anti Additions
 An addition that places the parts
of the reagent on the same side
(or face) of the reactant is called
syn addition syn
C C + X Y C C
addition
X Y

Pt
C C + H H C C
H H

Catalytic hydrogenation is a syn addition.

Ch. 7
 An anti addition places parts of
the adding reagent on opposite
faces of the reactant
Y
anti
C C + X Y C C
addition
X

© 2014 by John Wiley & Sons, Inc. All rights reserved. Ch. 7
14. Hydrogenation of Alkynes
H2 H H

Pt or Pd
H2

H H

H H
 Using the reaction conditions,
alkynes are usually converted to
alkanes and are difficult to stop at
the alkene stage Ch. 7
14A. Syn Addition of Hydrogen:
Synthesis of cis-Alkenes
 Semi-hydrogenation of alkynes to
alkenes can be achieved using either
the Ni2B (P-2) catalyst or the Lindlar’s
catalyst
● Nickel boride
O compound
NaBH4
(P-2
catalyst)
Ni
O CH EtOH
Ni2B
3 (P-2)
 2

● Lindlar’s catalyst
Ch. 7
 Semi-hydrogenation of alkynes
using Ni2B (P-2) or Lindlar’s
catalyst causes syn addition of
hydrogen
● ExamplesH2 H H
(97%)
Ni2B (P-2)
(cis)

H2 H H
Ph CH3 (86%)
Pd/CaCO3 Ph CH3
quinoline
Ch. 7
14B. Anti Addition of Hydrogen:
Synthesis of trans-Alkenes
 Alkynes can be converted to
trans-alkenes by dissolving metal
reduction
 Anti addition of dihydrogen to the
alkyne H
o
1. Li, liq. NH3, -78 C R'
R R' R
2. aqueous work up
H

Ch. 7
 Example

o
1. Li, liq. EtNH2, -78 C
2. NH4Cl

H
anti addition
Ch. 7
 Mechanism
radical anion vinyl radical
R R H
H NHEt
R C C R C C C C
R R
Li

Li

R H EtHN H R H
C C C C
H R R

trans alkene vinyl anion

Ch. 7
15. An Introduction to Organi
Synthesis
15A. Why Do Organic Synthesis?
 To make naturally-occurring compounds
which are biologically active but difficult
(or impossible) to obtain in quantity
AcO O OH
Ph O

BzN O
H OBz O Anti-cancer
H
HO OAc agent
TAXOL OH

Ch. 7
 TAXOL (isolated from Pacific yew
 tree)
Approved by the U.S. Food & Drug
Administration in 1992 for treatment of
several types of cancer, including breast
cancer, lung cancer, and melanoma
 An estimation: a 100-year old yew tree
must be sacrificed in order to obtain 300
mg of Taxol, just enough for one single
dose for a cancer patient
 Obviously, synthetic organic chemistry
methods that would lead to the synthesis
of Taxol would be extremely useful

Ch. 7
15B. Retrosynthetic Analysis –
Planning an Organic Synthesi
Retrosynthetic analysis
Z Y X W A
Target Immediate Earlier Next earlier Starting
molecule precursor precursor precursor compound

Z can be Y can be X can be W can be

synthesize synthesize synthesize synthesize
d from Y d from X d from W d from A
using using using using
certain certain certain certain
reagents reagents reagents reagents

Forward synthetic direction

Ch. 7
 When doing retrosynthetic analysis, it
is necessary to generate as many
possible precursors, hence different
synthetic routes, as possible
2nd precursor a
1st precursor A
2nd precursor b

2nd precursor c
target
1st precursor B
molecule
2nd precursor d

2nd precursor e
1st precursor C
2nd precursor f
Ch. 7
15C. Identifying Precursors
 Synthesis of

C C

(target molecule)

Ch. 7
 Retrosynthetic Analysis
o
SN2 on 1 alkyl halide: good

X
C C +
disconnection 1 

C C

disconnection 2 
 X +

o
SN2 on 2 alkyl halide: poor
 will get E2 as major pathway
Ch. 7
 Synthesis

NaNH2
C C H C C Na
liq. NH3

(SN2) I

NaI + C C

Ch. 7
Summary of Methods for the Preparation
of Alkenes
(Dehydrohalogenati
on
C C of alkyl halides) C C
H X base, heat H+ H OH
heat (Dehydratio
n of
H2, Ni2B (P-2) C C alcohols)
or Lindlar's catalyst Li, liq. NH3
(give (Z)-alkenes) (give (E)-alkenes)

C C (Semi- (Dissolving C C
hydrogenati metal
on reduction of
of alkynes) alkynes)
Ch. 7
 Summary of Methods for the Preparation
of Alkynes
X (Dehydrohalogenati Cl
H R' Cl R'
on of geminal
R H dihalide) R H
X NaNH2 NaNH2 H
heat heat
(Dehydrohalogenati R C C R'
on of vicinal
dihalide)
(Deprotonation of 1. NaNH2, liq. NH3
terminal alkynes and SN2 2. R'-X (R' = 1o alkyl group)
reaction of the acetylide
anion) R C C H

Ch. 7