Question

CHEM 232 Discussion Section Worksheet 11 be 1. Provide the reagent(s) needed to convert the given general functional group into a new product. Use the Synthesis Map to help you navigate between functional groups. Transform a primary alcohol into... a. An alkoxide An aldehyde An alkyl chloride An alkene A carboxylic acid O b. Transform an alkane into... An alkyl halide Transform a secondary alkyl bromide into... c. hc geoqor amaidog aiadie nbbdos wods o oubose sAn alcohol e An organolithium reagent shelaM pnihee tubon An alkene d. Transform chloromethane into... A Grignard reagent A symmetric ether Transform an aldehyde into... e. A primary alcohol A secondary alcohol An enone A carboxylic acid Transform a carboxylic acid into... f. An ester A primary alcohol

Answer 1

(a) Primary alcohol means in which -OH group is attached to primary Casson R-CH2-OH + Na - R-CH₂ONA / 24 1, e-cн, -он Рcc R-с но PC: Pyridinium chlorochromat I 1R-CH₂ - CH₂OH con Ho R-CH=CH alkaline King R-CH₂-Cooh NR-CH₂ CH₂ Ot audic Kecho . (b) Contenta de entantis CHytch hochzel

С) е око, ,014 сч, -ец –сн, 2 alkyl bromide 43-CH-CH3 , ен, -е-е, ты — CH3-CHLI CH] (ty eya-cycн, село ен,-CH=4 Ко

d)

(i) CH₃Cl + Mg ------------------> CH₃MgCl

When methyl chloride is treated with magnesium in presence of dry ether forms methyl magnesium chloride

(ii) Symmetric ether means both the alkyl groups attached to oxygen are same

When methyl chloride is treated with sodium methoxide forms Methoxy methane. This reaction is called William Son's synthesis.

CH₃Cl + CH₃ONa -------------> CH₃OCH_​3

E)

(i) When formaldehyde is treated with Grignard reagent forms primary alcohols

HCHO + CH₃MgCl --------> CH₃CH₂OH

(ii) CH₃CHO + CH₃MgCl --------> CH₃CH(OH)CH_{​​​​​3}

Whenaldehydesother than formaldehyde are treated with Grignard reagent forms secondary alcohols.

(iii)

When aldehydes having alpha hydrogen are treated with mild base undergoes condensation reaction form beta hydroxy aldehydes which on heating forms enones.

2 CH₃CHO ---------> CH₃CH(OH)CH₂CHO -------->

CH_{​​​​​3}​​​​CH=CHCHO

(IV) When aldehydes are treated with alkaline potassium permanganate or acidic potassium dichromate forms carboxylic acids.

RCHO ----------> RCOOH

F)

When carboxylic acids are treated with alcohols in presence of acids or bases, esters are formed.

RCOOH + ROH --------> RCOOR

When Carboxylic acids are treated with reducing agents like lithium aluminium hydride forms primary alcohols.

RCOOH + LiAlH_​​4 ---------> RCH₂OH