c) cis-2-hexene

b) 1-ethyl-4-isopropylcyclohexane

a) 2,2-dimethylbutane

d) ethylene

1. Draw the structure of the following compounds. Include all hydrogens in the structure (i.e. CH3CH3 rather than C-C for ethane).

e) (Z)-2-bromo-2-pentene

2. Hydrocarbon X has 50 carbons, 2 π bonds, and one ring. How many hytdrogens are present in a molecule of X ?

3. Complete the following Newman projection for the most stable conformation of octane viewed down the C3-C4 bond.

Answer

5. How many of the four methyl groups in the following structure will be equatorial in the more stable chair conformation?

CH3

CH3

CH3

CH3

4. Complete the wedge-dotted line structure for the following Newman projection:

H

Br

CH3

H

Br

H

H

CH3

H

CH3and

a)

CH3

CH3

HH

H

CH3and

b)

6. Indicate (in the boxes) the isomer relationship between the following pairs. Your only choices are constitutional, configurational, or conformational:

H

CH3

H

CH3

H

CH3CH3

H

CHCH2CH3

Give the formal charge on the indicated atom in the following structures:9.

C

CH3

CH3

Indicate (in the boxes) the acids and the bases in the following acid-base reaction:7.

For the above structure X:

Br

BrX

S OHF

O

O

S OHHO

O

O

S OF

O

O

S OHO

O

O

H

H

+(-)

a)

How many configurations are possible for molecules with the constitution of X?

b)

How many chirality centers are present in the structure of X?

CH3 C

CH3

CH3

CH3a) b)

8.

++

progress of reaction

ener

gy

AB

C

9. For the above energy diagram:

Which product (A, B or C) is formed at the slowest rate?

a)

Answer

Which product (A, B or C) is most stable?b)

Answer

10.

Which one of the above structures (A, B or C) would have (2R, 3R) as its configuration prefix?

a)

c)

Which two of the above structures are related as enantiomers?

Which one is properly termed a ‘meso compound’?

Answer

Answer

AnswerAnswer

+

OH

HO

CH3

CH3

H

H

A B C

b)

d) Which one is an achiral molecule?

Answer

H

H

CH3

CH3

OH

HOOH

H

CH3

CH3

H

HO

11. For the above four structures (A, B, C & D):

A

Which one is (1R, 2S)-1-bromo-2-methylcyclohexane?a)

b) Which one is identical to X (below)?

B C

Answer

Answer

BrBr

D

Br

CH3

BrCH3CH3CH3

X

Which one is the enantiomer of A?c)

e) If C has a specific rotation of (+)20o, which one must have a specific rotation of (-)20o?

Answer

Answer

d) Which two are diastereomers of B?

AnswerAnswer

and

Br

H

CH3

H

f) Which one would be mixed with D to form a racemic mixture?

Answer

A B C

CH312.

Which of the above three carbocations (A, B or C) is the most stable?

Answer

(+)CH2(+)

CH3(+)

H

A B C

CH313.

Which of the above three olefins (A, B or C) releases the least heat upon catalytic hydrogenation to form methylcyclohexane?

Answer

CH3 CH2

Draw the structure of Compound X (C10H16) in the box, based on the following ozonolysis result:

14.

O3

Zn,H3O+

1)

2)

Compound X(C10H16)

CH3C

CH2C

CH3

O O

HC

CC

H

O O

CH3 CH3

+

c)

Draw the structure of the major organic product of the following reactions.15.

16. Draw the structure of the olefin monomer (in the box) used to make the following polymer:

a)BH3

b)

H2SO4

H2O2, NaOH

1)

2)

show stereochemistry

CCH3

CH3

CHCH2CH3H2O,

NaBH4C

CH3

CH3

CHCH2CH3Hg(OAc)2, H2O1)

2)

d)

NMOC

CH3

HC

OsO4H

CH3

show stereochemistry

e)

CCH3

HC

CH3

H

show stereochemistry

+

C

Cl

O OO

H

CO2H

Cl

olefin monomer

CH2 CH CH2 CH CH2 CHROOR

CH3

polymer

Draw appropriate structures in the boxes:17.

a)

CCH3

CH3CHCH2CH3 HBr+

more stable carbocation intermediate major organic product

b)

Br2/H2O+

bromonium ion intermediate, show stereochemistry with wedge/dotted lines

major organic product, show stereochemistry

CH3

c)

initial carbocation

organic product

CH

HCl

1,2 hydride shift

rearranged carbocation

CH2

Cl(-)