Provide the major products and reaction names for the following transformations: a) 1-chloropropane to…

Question

Provide the major products and reaction names for the following transformations: a) 1-chloropropane to propanoic acid, b) But-2-ene to butane-2,3-diol, c) But-2-ene to butane-2,3-diol using OsO4.

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Here are the completed equations and the names of the major products: a) Step 1: CH₃CH₂Cl undergoes an SN2 reaction with KCN to form a nitrile. Step 2: The nitrile is then hydrolyzed under acidic conditions to a carboxylic acid. CH₃CH₂Cl 1. KCN, EtOH, Heat CH₃CH₂CN 2. H₂O, H^+, Reflux CH₃CH₂COOH Product name: Propanoic acid b) Step 1: The alkene undergoes epoxidation with a peroxy acid (RCO₃H). Step 2: The epoxide is then opened by acid-catalyzed hydrolysis to form a trans-diol. CH₃CH=CHCH₃ 1. RCO₃H, CH₂Cl₂ Epoxide intermediate 2. H₃O^+ CH₃CH(OH)CH(OH)CH₃ Product name: Butane-2,3-diol c) Step 1: The alkene undergoes syn dihydroxylation using osmium tetroxide (OsO₄) and pyridine. Step 2: The osmate ester is then cleaved by $NaHSO₃/H₂

Provide the major products and reaction names for the following transformations: a) 1-chloropropane to propanoic acid, b) But-2-ene to butane-2,3-diol, c) But-2-ene to butane-2,3-diol using OsO4.

Answers

Step-by-step solution

Part a· 2 steps

$\text{CH}_3\text{CH}_2\text{Cl}$ undergoes an $\text{S}_{\text{N}}2$ reaction with $\text{KCN}$ to form a nitrile.

The nitrile is then hydrolyzed under acidic conditions to a carboxylic acid.

Part b· 2 steps
$\text{CH}_3\text{CH(OH)CH(OH)CH}_3$

The alkene undergoes epoxidation with a peroxy acid ( $\text{RCO}_3\text{H}$ ).

The epoxide is then opened by acid-catalyzed hydrolysis to form a trans-diol.

Part c· 2 steps

The alkene undergoes syn dihydroxylation using osmium tetroxide ( $\text{OsO}_4$ ) and pyridine.

The osmate ester is then cleaved by $\text{NaHSO}_3/H_2

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Provide the major products and reaction names for the following transformations: a) 1-chloropropane to propanoic acid, b) But-2-ene to butane-2,3-diol, c) But-2-ene to butane-2,3-diol using OsO4.

Answers

Step-by-step solution

Part a· 2 steps

CH3CH2Cl\text{CH}_3\text{CH}_2\text{Cl}CH3​CH2​Cl undergoes an SN2\text{S}_{\text{N}}2SN​2 reaction with KCN\text{KCN}KCN to form a nitrile.

The nitrile is then hydrolyzed under acidic conditions to a carboxylic acid.

Part b· 2 stepsCH3CH(OH)CH(OH)CH3\text{CH}_3\text{CH(OH)CH(OH)CH}_3CH3​CH(OH)CH(OH)CH3​

The alkene undergoes epoxidation with a peroxy acid (RCO3H\text{RCO}_3\text{H}RCO3​H).

The epoxide is then opened by acid-catalyzed hydrolysis to form a trans-diol.

Part c· 2 steps

The alkene undergoes syn dihydroxylation using osmium tetroxide (OsO4\text{OsO}_4OsO4​) and pyridine.

The osmate ester is then cleaved by $\text{NaHSO}_3/H_2

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$\text{CH}_3\text{CH}_2\text{Cl}$ undergoes an $\text{S}_{\text{N}}2$ reaction with $\text{KCN}$ to form a nitrile.

Part b· 2 steps
$\text{CH}_3\text{CH(OH)CH(OH)CH}_3$

The alkene undergoes epoxidation with a peroxy acid ( $\text{RCO}_3\text{H}$ ).

The alkene undergoes syn dihydroxylation using osmium tetroxide ( $\text{OsO}_4$ ) and pyridine.