Synthetic Routes (DP IB Chemistry: HL)

The synthesis of ethyl butanoate can be carried out in three steps:

                                         I                   II                      III

                        C₄H₉Br   →  C₄H₉OH  →  C₃H₇COOH  →  C₃H₇COOC₂H₅  

What is the correct classification of the steps?

The synthesis of 2-propyl propanoate can be carried out in two steps:

                                               I                                

                         CH₃COCH₃   →  CH₃CH(OH)CH₃

                                               II   

                  CH₃CH(OH)CH₃  → C₂H₅COOCH(CH₃)₂ 

What are the reagents needed in I and II?

The synthesis of phenylamine can be carried out in two steps:

                                   I                    II             

                      C₆H₆   →  C₆H₅NO₂   → C₆H₅NH₂                                  

What are the reaction types in I and II?

Which of the following reactions produces only pentan-2-ol?

Which compound could be X in this two step reaction pathway?

C₃H₈ → X  → C₃H₇OH

The equation below shows the conversion of propanal to propyl ethanoate.

  What are the reagents used and the reactions taking place?

But-1-ene reacts separately with HBr and H₂/ Ni to give products X and Z respectively. 

What are the major products of the reactions?

	X	Z
A.	CH2BrCH2CH2CH3	CH3CH2CCH
B.	CH3CH2CH2CH2OH	CH3CH2CH2CH3
C.	CH3CHBrCH2CH3	CH3CH2CCH
D.	CH3CHBrCH2CH3	CH3CH2CH2CH3

Methylbenzene can be converted into 4-methylphenylamine in a multi-step reaction.

Which order should the reagents be used to do this conversion? 

Which alcohol could not be produced by the reduction of an aldehyde or a ketone?

Which molecule(s) can be both reduced by sodium borohydride, NaBH_4, and oxidised by warm acidified potassium dichromate (VI)? 

1. CH₃CHBr(CH₃)₂CCHO
2. CH₃CHOHCH₂CH₃
3. (CH₃)₃CCHO