The LP on N is localized, soit

will be considered when determines

hybridization

(e- deficient)

(e- rich)

EXAM 1 PRACTICE PROBLEMS

Hi everyone! I will be holding an exam review on Monday, Jan. 25

th at 5:00-6:50pm. I recommend that you all join so we

can go over the problems. Please attempt to complete this review on your own over the weekend! I recommend that youstudy by prioritizing your book + the book problems, homework problems, and the worksheets. Complete this practicetest once you feel you have utilized all other study aids to test your knowledge! If you are having trouble understandingcertain concepts it would be a good idea to read your book chapters and review your lecture notes.

1. Convert each condensed formula to line-bond structure

a. (CH

3)

3CCH(OH)CH

2CH

3

b. (HOCH2)

2CH(CH

2)

3C(CH

3)

2CH

2CH

3

2. Calculate the formal charge for each nitrogen, carbon, and oxygen

3. Classify each compound as isomers, resonance structures, or neither

A + B:A + C:A + D:

XpOH

arrHo l X'OH

I 2 1 23

N :S -4=+1 O , :b- 6=0

N :S -4=1-1 Ci : 4-4=0

Cz : 4-5=-1Oz :b - 5=+1

Og : 6-7=-1

(211402 (211402 Cztlgoz0211402

Resonance structures

Neither

Isomers

B + D:

4. Draw a second resonance structure

5. Draw a second resonance structure and identify the major and minor contributors.

6. Put the following compounds in order of increasing bond lengthH—F H—Br H—Cl

7. Put the following compounds in order of decreasing bond length(CH

3)

2NH (CH

3)

3CH CH

3OH

8. Match the hybridization with their geometry and bond angle

Sp __ a. tetrahedral, 120 degrees

Sp

2 __

b. linear, 180 degrees

Isomers

+

c .

F - retro?H :O:

AEng cuz- E-liq-"3 I

'

nn ah

t :O : i

b . as"i ,i" d

.

CHA. - inningc- e - C N

i'

Iµ H

H

'i' t

. BABEminor

masorlmorebonds.US#arges)

H

• a vttitfffffyfN IEqual H H

HFcHchHBrI '¥yJatogm¥*The larger the atom,

the longer

its bond I

* Whenranking acidity

→

*The more electroneg .the C N O F atoms in same

row, look@

atom,the shorter the bond A ¥neg ,

electronegativity . Atoms in

(CH3) 3 CH s CCH3)ZNHSCHZOH the same column , look@

longest shortest atomic site *

Sp

b F

C # Spc

Gsp's

Sp3 __ c. trigonal planar, 120 degrees

d. Tetrahedral, 109.5 degrees e. Linear, 190 degrees

9. Determine the hybridization and molecular geometry around the nitrogen, and oxygen

10. Predict the indicated bond angles in each compound

11. What orbitals are used to form each bond?

12. How many sigma and pi bonds are there in each molecule?

d

y - µ.

µHybridization: gp3

→ Molecular geometry : bent ( 104.50)

-Hybridization: Sp 's

Molecular geometry: bent

1000

wooSp , linear : 1800

1200Spl : 120

°

120

pa-5

109.50gp3 : 109.50

H2

l : Csps - Gp2←

3 2 :(gp2 - His

11 ¥ 3 : Csp - HISsingle : I 0 bond

double : I 6 bond + IT bond

*triple : I 0 bond t 21T band

G :3 IT : I = G : 8 IT :3a . b . oh

o H

C. get 6:12 IT :L d

.

N"

:

G : 6IT : 2

- ④HO

mom:÷÷i÷÷÷÷÷EEnEE÷÷:sE÷÷÷ooe"÷÷÷÷:*. "

Oi. 937g! planar- add

" ""

do. :*.ua#an-an--srm:.ans:÷÷¥÷÷÷÷÷no.M

-

E- Bent

nbeqgyadfqny.mndetermining

13. Which of the bonds shown in red in each compound or pair of compounds is shorter?

14. Indicate which of the following molecules is polar. Show the direction of the net dipole if it has one.

a. CH2Cl

2

b.

c.

15. Which compounds are Bronsted-lowry acids?HBr NH

3 CCl

4

16. Which compounds are Bronsted-lowry bases?

17. Classify each compound as an acid, a base, or both

* inc .in s - character = bond

strength increases and bond lengthdecreases bc the e

- are held

closer to the

sp sp2

Sp's nucleus wi

- TS-char .

inc. length

sp's

spa

Clf-polar

µ111£81

A

H

Qf

polar.

I

f Nonpolar . No net dipole

£

acidBronsted-Lowry : must have a Hydrogen

that can be

lost as Ht . Any substance that donates a proton(Ht)

d - proton donor :acid t base

amphoteric(has a LP t H)

Bronsted base: Ht acceptor

1 . LPd d2. C-I chargeBL- Acid LP w/

neg- charge

d d: :

acid t acid 19 acid t

No' Base ( LP)BaseUP) ( htt

18. Label the acid and base, predict the products, and identify the conjugate acid and base in the following reactions. Use

curved arrows to show the movement of electron pairs

19. Decide which compounds is the acid and which is the base. Write the mechanism and draw the products.

20. Draw the mechanism and the products of each reaction and determine the direction of equilibrium.

- I

+ :c:i :-

. a- uAcid Base T conj . acid Cong - base 1

Vs'

proton proton ( gained att) ( lost Ht )'

( donor ) (acceptor) weak acid'

strongacidmore stable O

*f .t

'' !us.

-

TH Litt Ty '

Hconj . Con ) -

I acid 1

acid Basebase

strong' ARIO :

weak :O:'

acidacid t ! O > C

#

AS.B.

5. A.→ W-AARIO

y

t HEBresonance'

w . B.

Cons - acid inductionacid

baseT cons . bae W -A.

S.A -

A.

↳ :-

t H2T

acid Baseconj - acid

strong conj. base

base pKa-

- 25

PKa -- 34

Iifa D- Iit" t i .ci :-

us. O- nine

#CONJ-acid - cons.

Base S -A .

acidbase Atomic

W -A -ARIO Effect

high→ low energy5.A.→ WA

.

:O :tf ly +"or

base cons . acid- cons.acidT base W

-A '

S.A .

21. Rank the hydrogens in order of increasing acidity

22. Which compound is the stronger acid?

23. For each pair of compounds, which indicated H is more acidic?

24. Rank the compounds in each group in order of increasing acidity

ion isv .

stable*

* chlorine

AH . it

or

Base Acid & cons . cons - base

W-A .

acid

S.A .

strongestgeU0neg - across a row

weakest iCN O F

ssg.rfindc.ws#eacoiumn&ror9m..rdldhtI

N-HSOHCSH ARIO

* atomic effect:

-. ÷ → C-H vs . O - H electroneg !

-- O > C

A-RIO

- c-H vs . O- H

which is more likely to donate all ?

Sp > spz > sp?T s char = increase

Sp : so -

i. Schar .in acidity

sp -His Sp 's - His

spa : 33-1. Schar. ARIOsp 's : 25% Schar.

SPZ - Hls Sp 's - His

ix. electrons .

cN0→f Atomic effect :

electroneg .

:

A B C csnso ARIOAccs B

Ha ! If we deprotohate(remove

A H from the acid w/ a base)

Ha , we would be able to form

a resonance structure .

Removing Hb would not allow US

to create a resonance structure

T oHb 0

g-Base 1112 11 - Jin

i

⑨ I° "11 so ,

*af:*

ARIO

*Bases stabilized bythe ARIO factors are

ARIOweak bases (themore

stable a base → the

-a.least

stable-_

Weaker it is *

on! Eminescu.cn, most basic!

Een%?I ginsmost stable (O is very electro neg → stabilizesthe f) charge ) Br

q* I s

.

ARIO

Br-

s HO-

L THz

A-RIO

yleast stable

base (no

°resonance

or

S -O-

induction )=

Full o- L"#

o-L.to-

strongestbase

qw*F is

more

weakest electroneg.

-than

base .Resonance t Cl , so

F willbe

inductionstabilised more stable

=

weakestbase!

A

ARIO

* Acidity : spsspz> sp3*

D= :'s ,

a'espastnsytarbianeaie=strongest

base!

Sp spin sp's

25. Which anion (A or B) is the stronger base?

26. Which are lewis bases?

NH3

CH

3CH

2CH

3

H:

-

keep it as an acid

27. Which are lewis acids?BBr

3

CH

3CH

2OH

A B c Resonance t Inductive effect

:

CCBC A ARIO

N -H ¥"c-H O-H

atom effect ARIO

A c -Bc N o Fqienuitroneg .

BLAS C

CH c NHL OH

* The more stable a base is→

Resonance! the less basic t

more stable

base No resonance

C-delocalizedless stable

base

e- localized

( ( P)Lewis Base : electron pair donor

(no LP)

C-I charge

.ee

Hall browsedd

Lewis Acid : electron pair acceptor

Br -B,

- Br- no filled valence shell (Only he e

-)

cowry acids Br

are Lewis i can also be lewis base

acids → not

all lewis acids&

Are Bronsted acids *

(CH

3)

3C

+

Br

-

28. For each reaction, label the lewis acid and base. Predict the products and show the mechanism

29. Classify each alkyl halide and alcohol as primary, secondary, or tertiary

30. Classify each amine in the following compound as primary, secondary, or tertiary

31. What types of intermolecular forces are present in each compound?

(f) charge→ not filled valence shell

i ! : filled valence shell → not Lewisacid

F

T , for CHSF - B - O

→ i n

Only F CHSLewis lewis

• valence Acid Base

e- in (e- acceptor) (e - donor

)

shell = T : ,OH-

e- deficient

Lewis acid page(e- acceptor)

Lewis

(e- donor)

(°

•

A o 2°

i ro lo• a o

@ 0 a

20

VDM VPN, D-D VDW , D - D , H -bonding

32. Which compound in each pair has the higher boiling point?

33. Predict which compound in each pair has the higher melting point

Functional Groups

34. Identify the functional groups present in each molecule. (add phenol, alcohol, ketone, aldehyde, and ether)

*D- D= Dipole- Dipole#

VDW VDW t D-D * more energy req. to overcome

more IMFS *

VDWID-D, vow , D- D electronegH -bonding →

vow . row .Effing *9871mg ,

D- Dp - D

Ilook @ sited

VDW H- bond ,dipole

-dipole , VDWEA nadon↳ dis p -✓ forces )

* increase in symmetry = increase in MPA

9

symmetric

* H -bonds : only 0.N.FI

tf

an:z Fannief = alkene

Ester= = alkyne

idrown

'

~ = alkanepre

eaeidgiiine far

9'

A lamide phenyl

Generalaromatic

aromaticGH fawn

" ⑧hyde

OH -O

I o

9 '

II

pretty and foketone

alkyl halide alcohol ether amine

thiol sulfide aldehyde ketone

carboxylated ester amide acid chloride

monophosphate di - phosphate triphosphate acyl phosphate

0

Knotanhydride