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Increasing carbon chain using alkyl halide

NaCN (acetone, SN2) → adds -CN (adds 1 carbon)

Extend chain from terminal alkyne

1. NaNH2 2. R-CH2Br → longer alkyne

Role of NaNH2 with terminal alkyne

Deprotonates to form acetylide ion (strong nucleophile)

Forming an internal alkyne

1. NaNH2 2. Alkyl halide (R-CH2Br)

Alkyne reaction with aldehyde/ketone

1. NaNH2 2. Carbonyl 3. H2O → alcohol

Alkyne opening an epoxide

1. NaNH2 2. Epoxide 3. H3O+ → extended chain alcohol

Ozonolysis purpose

Cleaves double/triple bonds

O3 + H2O result

Carboxylic acids + CO2 (oxidative)

O3 + H2O2 result

Strong oxidation → aldehydes → carboxylic acids

Reductive ozonolysis

O3 + DMS (or Zn/H2O) → aldehydes/ketones

Ozonolysis of rings

Opens ring → dicarbonyl compounds

Alkane to alkyl halide

Br2, hv (radical halogenation)

Alkyl halide to alkene

E2 with bulky base (e.g., (CH3)3COK)

SN2 conditions

Strong nucleophile + primary substrate

NBS function

Allylic bromination (hv)

Strong nucleophile + alkyl halide

SN2 substitution

Alkene to alkyne

1. Br2 → vicinal dihalide 2. xs NaNH2 → alkyne

Vicinal dihalide definition

Two halogens on adjacent carbons

Alkyne to alkane

H2, Pd/C (full hydrogenation)

Alkyne to cis-alkene

H2, Lindlar's catalyst

Alkyne to trans-alkene

Na, NH3 (liquid)

Acid hydration of alkyne

HgSO4, H2SO4 → ketone

Hydroboration-oxidation of alkyne

1. R2BH 2. H2O2, NaOH → aldehyde

Ozonolysis of alkyne

Carboxylic acids (+ CO2 if terminal)

Retrosynthesis definition

Work backward from product to starting materials

Chain extension strategy

Use acetylide ion + SN2

Chain shortening strategy

Use ozonolysis