Organic Synthesis

Suggest the structures of compounds T and U and draw them in the boxes above.

Suggest reagents and conditions for steps 1-5.

step 1 .........................................................................................................................................

step 2 .........................................................................................................................................

step 3 .........................................................................................................................................

step 4 .........................................................................................................................................

step 5 .........................................................................................................................................

What types of reaction are steps 1 and 5?

step 1 .........................................................................................................................................

step 5 .........................................................................................................................................

$\text{Br}_2(\text{aq})$

$\text{Na}(\text{s})$

$\text{I}_2(\text{aq}) + \text{OH}^-(\text{aq})$

2,4-dinitrophenylhydrazine

Based upon the results of the above tests, suggest structures for compounds D and E.

D, $\text{C}_4\text{H}_8\text{O}$:

E, $\text{C}_3\text{H}_4\text{O}_3$:

Compound C exists as two stereoisomers.

Draw the structural formula of each of the two isomers, and state the type of stereoisomerism involved.

type of stereoisomerism .......................................................

Abscisic acid is reacted with an excess of $\text{NaBH}_4$.

Give the molecular formula of the organic product formed.

Draw the skeletal formula of the carbon-containing product with the largest molecular mass.

Identify the carbon-containing product with the smallest molecular mass. Explain how this product arises.

Identify the third carbon-containing product of this reaction by giving its displayed or structural formula.

Suggest the structures of compounds H and J and draw them in the boxes above.

Suggest reagents and conditions for steps 1-6.

step 1 .........................................................................................................................................

step 2 .........................................................................................................................................

step 3 .........................................................................................................................................

step 4 .........................................................................................................................................

step 5 .........................................................................................................................................

step 6 .........................................................................................................................................

Suggest structures for the starting material P and the intermediate Q.

Suggest reagents and conditions for the following steps in the above scheme.

step 1 ..................................................................................................................

step 2 ..................................................................................................................

step 4 ..................................................................................................................

Suggest reagents and conditions for steps 1–4.

step 1 $\text{..................................................................................................................}$

step 2 $\text{..................................................................................................................}$

step 3 $\text{..................................................................................................................}$

step 4 $\text{..................................................................................................................}$

Name the mechanism of step 2 and state the type of reaction in step 4.

mechanism of step 2 $\text{..........................................................................................................}$

type of reaction in step 4 $\text{....................................................................................................}$

Suggest the identities of the compounds B–E by drawing their structures in the boxes.

State the reagents and conditions for the following steps.

step 1: ..................................................................................................................................

step 3: ..................................................................................................................................

step 4: ..................................................................................................................................

step 6: ..................................................................................................................................

If the amount of $\text{ClCOCOCl}$ used in step 2 is decreased, another compound is formed in step 2 with the molecular formula $\text{C}_{14}\text{H}_8\text{O}_2\text{Cl}_2$.

Suggest the structure of this compound.

Identify all the steps in the synthesis of Q from benzene that are electrophilic substitution reactions.

Use this information to suggest the two functional groups, taken from the list on page 10, that each compound contains.

Suggest a structure for each compound.

Suggest the identities of compounds Y and Z by drawing their structures in the boxes.

Suggest suitable reagents and conditions for each of the steps 1–3.

step 1: ..................................................................................................................................

step 2: ..................................................................................................................................

step 3: ..................................................................................................................................