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CHM556 Sept 2012 Jan 2013 Carbonyls and Carboxylic Acids Assignment 1 Question 1 Predict the products of the

e following transformations:
A H2O, H3O+ 2CH3OH, H3O+ B

+ _ Ph3P-CH2

H2NNH2 F
NH2

1. HCN 2. (a) LiAlH4, THF (b) H2O C CH3MgBr, H3O+

Question 2 How would you prepare:


O O

a) b) c) d)

HC(CH2)3CH

from an alkene

2-butanone from an alkyne Acetic acid from dry CO2 2 molecules of butanoic acid from an alkene

Question 3 Predict the products of the following reactions:


O CH3CH=CHCH 2H2, Ni X

NaBH4

Question 4 Draw the mechanism for a base-promoted -halogenation of the following compound:
O CH(CH3)2 Br2 NaOH

Question 5 Predict the product for each of the following reactions:


a)
CO2CH2CH3 2CH3CH2MgBr H2O CH3 CH3 LiAlH4 H2O

b)

H2C=CHCHCH2CO2CH3

c)

CH3CHCH2CH2C

2H2O H+

OH

d)

CH3CO2COCH3 Pyridine

e)

COCl

CH3NH2

f)

CONH2 CH3

LiAlH4 H2O

g)

CO2H H H CH3

CH3OH H2SO4

h)
Br

CO2H

SOCl2

i)

CO2H

NaHCO3

COCl

j)

H2O, NaOH

Question 6 How would you prepare the following products from propanoic acid? (Some may require more than one step.) a) CH3CH2CH2OH b) CH3CH2CHO c) CH3CHBrCH3 d) CH3CH=CH2 e) CH3CH2CH2NH2 Question 7 Arrange the following compounds in order of increasing reactivity with ammonia, NH3. Explain your answer.
O H3C Cl H3C O O CH3 H3C O O O CH3

Question 8 Provide the major products of the following equations. Include the intermediate(s) where necessary.
O a) O 2CH3OH H3O+ O c) CH3CH2NH2 Cl d) O CH3COCH3 H2O O e) O O OH H O g) H O NH2 LiAlH4 O h) H 3C C H3 Ph 3P-CHPh O b) H 1. HCN 2. H3O+, heat

MgBr

CH3OH

f)

SOCl2

COOH i)

1. NaOH 2. HCl

O j) Ph O Ph

PhNH 2

O k) Ph Ph

PhNH2

Question 9 Arrange the following pairs of compounds in order of increasing reactivity with a nucleophile. Explain your answers.
O O O CH3 O O CH 3 O N H 2 and H 3 C Cl

i)

and

ii)

H 3C

Question 10 (Revision) Starting from benzene, how would you synthesize benzyl phenyl ether below? More than one step is required.
O Benzyl phenyl ether

Question 11 (Revision) Suggest how you would carry out the following transformations. Some may require more than one step.
O

(a)

OH OH

(b) 1-Butanol
O

2 mols of ethanol OH CH3CH2CCH2CH3 CH3

(c)

(d) CH3CH2CCH2CH3

(e)

1-Bromobutane

Pentanoic acid