Homework - Review of Chem 2310

Name ____________________________________

1. Fill in the following partial Periodic Table of Table of Elements. Do as much as you can from memory.

2. Using the Table above, circle the more electronegative atom in each pair.

a) nitrogen oxygen

b) carbon hydrogen

c) chlorine carbon

d) carbon nitrogen

e) oxygen fluorine

f) carbon oxygen

3. What is an isotope?

4. Give the number of valence electrons of each of the following elements.

a) oxygen

b) hydrogen

c) chlorine

d) lithium

e) bromine

f) nitrogen

g) iodine

h) carbon

i) sodium

j) aluminum

k) boron

l) sulfur

m) magnesium

n) phosphorus

o) potassium

5. Draw the Lewis structure for each of the following elements, and tell how many covelent bonds you would expect each to form (no charges).

a) carbon

b) nitrogen

c) oxygen

d) hydrogen

e) bromine

f) phosphorus

g) sulfur

h) chlorine

HW Review p 2

6. Draw complete Lewis structures for three compounds with the formula C2H5NO (and no charged atoms).

7. Give the molecular formula for the following line structures.

a) b)

c) d)

NH2

O

BrN

8. Give the unsaturation number for each of the following molecular formulas, and draw one possible structure for each.

a) C5H10O b) C5H12O

c) C5H11N d) C5H8O2

9. Give the geometry of all atoms (except hydrogen) in each of the following compounds.

a) b)

O

O OH

c)

H

N

d)

N

HW Review p 3

10. Label the polar bonds in each of the following molecules (ignore C-H bonds) using partial charges

(!+, !-) or polarity arrows.

a)

Br

b)O

c)O

Hd)

O

Cl

11. Give the hybridization of each atom (except hydrogen) in the following compounds.

a) b)

O

O OH

c)

H

N

d)

N

12. Label each molecular orbital and give the atomic orbitals that it came from in the following compound.

N

O

Br

ab c

d e

fg h

i

a)

b)

c)

d)

e)

f)

g)

h)

i)

13. Draw resonance structures for the following compounds, using arrows to show where the electrons go.

a)

O

O

HW Review p 4

b)

14. Give the charge next to each atom in the following compounds which has a charge.

Oa) b) O H c)NH

e) NHd) f)O

H

15. Give all functional groups which the following compounds contain.

a)O OH

b) c)O

H

NH2

O

d) e) f)Cl

ON

O

O

Cl

O

HO NH

O

16. What functional groups do the following compounds contain?

a) 2-pentyne

b) 2-pentanone

c) trans-2-pentene

d) methyl pentanoate

e) pentanal

f) 2-cyanopentanoic acid

g) 2-pentanol

h) 2-pentanamine

HW Review p 5

17. Which intermolecular force will be the most important in the the following compounds?

a) b) c)

d) e) f)

OH

H

O

N

O

OH

Br

18. Choose the compound in each pair which will have the highest boiling point, and briefly explain your choice.

a)

b) OH

c)

d) OH

O

e)NH2

NH

19. Choose the compound in each pair which will be the most soluble in water, and briefly explain your choice.

a)

b)

c) OH O

NH2

O O

HW Review p 6

20. Assign each of the following IR's with one of the compounds shown (not all compounds will be used).

OH

N

OH

O

O

NH2

A

B

C

D

E

F

G

H

___

___

___

___

___

___

HW Review p 7

21. Give the relationship between each of the following compounds (identical, constitutional isomers, enantiomers, diastereomers, meso, not isomers).

a) b)

c) d)

e) f)

g) h)

OH

OH OH

OH

Cl Cl

NH2 NH2

22. Draw correct line structures for the following compounds.

a) 3-ethylhexane b) 1-chloro-1-methylcyclopropane c) (Z)-3-methyl-2-pentene

d) (R)-2-bromopentane e) 3-methyl-4-penten-1-yne f) bicyclo[0.3.4]nonane

g) 2-cyclopropylbutane h) cyclononyne i) (trans)-1,3-hexadiene

HW Review p 8

23. Give correct names for the following structures.

a) b)

c) d)

e) f)

Br

24. Circle the stronger acid in each pair, and briefly explain your choice.

a)OH SH

b)

c)

OH OH

d)

e)

OHOH

Cl

NH2 OH

25. Draw the Fischer projection for the following compound.

O

H

OH

OH

OH

OH

HO

HW Review p 9

26. Draw a chart showing the chemical shift, integration, and splitting for each of the following spectra. Then deduce their structures.

a)

b)

C7H12O3

C8H10O

27. Choose the correct answer.

a) If the Keq is >1, the reaction is (favorable / unfavorable).

b) If the !G is > 0, the reaction is (favorable / unfavorable).

c) If you take away a product from a reaction at equilibrium, more (products / reagents) will be

formed.

d) If you heat a reaction, the rate will (increase / decrease).

e) If you increase the concentration of a reagent which is in the rate limiting step, the reaction rate

will (increase / decrease).

HW Review p 10

28. Write the pKa of the acid on each side of the equation below it; then, use them to predict whether the products or reactants will be favored by the equilibrium.

a)

b)

c)

O+ H2SO4 O + HSO4

-

H

+ NaOH Na+ + H2O

OH

O

+ NaHCO3O

O

Na+ + H2CO3

29. What is an electrophile?

30. What is a nucleophile?

31. What is the difference between a base and a nucleophile?

32. Label the following as nucleophiles or electrophiles.

a) b) c)

d) e) f)

g) h) i)

Na+

Br CH3OH

CH3Br

CH3+

Br2

CH3O-

HW Review p 11

33. Using your knowledge of nucleophiles and electrophiles, draw arrows to show how the following species will react with each other (1st step only) and give the immediate product.

a)Br

b) Br

HO

c)

Br Br

d)Br

34. Draw the complete mechanisms of the following reactions.

a) methane + bromine + heat or light methyl bromide + HBr + byproducts

b) ethyl bromide + sodium hydroxide ethyl alcohol + sodium bromide

c) tert-butyl iodide + sodium ethoxide 2-methyl-1-propene + ethanol + sodium iodide

(cold, dark)

HW Review p 12

d) cyclopentene + sulfuric acid + water cyclopentyl alcohol

35. Give all products of the following reactions (except stereoisomers of chiral compounds).

Br

NaOH

Br2

Cl

O Na

O3

H2O2

a)

b)

c)

d)

e)

f)

g)

HCl

2 eq HCl

KMnO4

H2O, NaOH

HClh)

HW Review p 13

BrBrBr

NaINaINaI

acetone

i)

j)

acetoneacetone

Na, NH3

Br

Cl

OH

CH3OOCH3

HBr

SH

S Na

1. Hg(OAc)2, H2O

2. NaBH4

1. BH3-THF

2. H2O2, NaOH

k)

l)

m)

n)

o)

p)

q)

r)

heat

H2O

H2SO4, Hg(OAc)2

Br2

H2, Pd/C

HNO3

H2Os)

HW Review p 14

1. O3

2. (CH3)2St)

u)

Br

(CH3)3COK

w)

x)

y)

z)

aa)

bb)

cc)

dd)

v)

O3, H2O

1. disiamylborane

2. H2O2, NaOH

2 eq Br2

KMnO4

H2O, NaOH

H2, Pt/C

I2, H2O

ClNaCN

Ph OO

H

O

Br Br 2 eq NaNH2

2. H2O

HW Review p 15

ee) H2, Lindlar

ff)

Cl

Cl

2 eq NaNH2

36. Write a reaction sequence (starting materials, reagents, and products for each step) by which the following transformations could be accomplished.

a) OH

b)

c)

d)

O

(3 steps)

(3 steps)

(2 steps)

Cl

H

O

H

O

(2 steps)

2. H2O